Dr. Laurie Starkey

Dr. Laurie Starkey

Nomenclature

Slide Duration:

Table of Contents

Section 1: Introduction to Organic Molecules
Introduction and Drawing Structures

49m 51s

Intro
0:00
Organic Chemistry
0:07
Organic
0:08
Inorganic
0:26
Examples of Organic Compounds
1:16
Review Some Chemistry Basics
5:23
Electrons
5:42
Orbitals (s,p,d,f)
6:12
Review Some Chemistry Basics
7:35
Elements & Noble Gases
7:36
Atom & Valance Shell
8:47
Review Some Chemistry Basics
11:33
Electronegative Elements
11:34
Which Is More Electronegative, C or N?
13:45
Ionic & Covalent Bonds
14:07
Ionic Bonds
14:08
Covalent Bonds
16:17
Polar Covalent Bonds
19:35
Polar Covalent Bonds & Electronegativities
19:37
Polarity of Molecules
22:56
Linear molecule
23:07
Bent Molecule
23:53
No Polar Bonds
24:21
Ionic
24:52
Line Drawings
26:36
Line Drawing Overview
26:37
Line Drawing: Example 1
27:12
Line Drawing: Example 2
29:14
Line Drawing: Example 3
29:51
Line Drawing: Example 4
30:34
Line Drawing: Example 5
31:21
Line Drawing: Example 6
32:41
Diversity of Organic Compounds
33:57
Diversity of Organic Compounds
33:58
Diversity of Organic Compounds, cont.
39:16
Diversity of Organic Compounds, cont.
39:17
Examples of Polymers
45:26
Examples of Polymers
45:27
Lewis Structures & Resonance

44m 25s

Intro
0:00
Lewis Structures
0:08
How to Draw a Lewis Structure
0:09
Examples
2:20
Lewis Structures
6:25
Examples: Lewis Structure
6:27
Determining Formal Charges
8:48
Example: Determining Formal Charges for Carbon
10:11
Example: Determining Formal Charges for Oxygen
11:02
Lewis Structures
12:08
Typical, Stable Bonding Patterns: Hydrogen
12:11
Typical, Stable Bonding Patterns: Carbon
12:58
Typical, Stable Bonding Patterns: Nitrogen
13:25
Typical, Stable Bonding Patterns: Oxygen
13:54
Typical, Stable Bonding Patterns: Halogen
14:16
Lewis Structure Example
15:17
Drawing a Lewis Structure for Nitric Acid
15:18
Resonance
21:58
Definition of Resonance
22:00
Delocalization
22:07
Hybrid Structure
22:38
Rules for Estimating Stability of Resonance Structures
26:04
Rule Number 1: Complete Octets
26:10
Rule Number 2: Separation of Charge
28:13
Rule Number 3: Negative and Positive Charges
30:02
Rule Number 4: Equivalent
31:06
Looking for Resonance
32:09
Lone Pair Next to a p Bond
32:10
Vacancy Next to a p Bond
33:53
p Bond Between Two Different Elements
35:00
Other Type of Resonance: Benzene
36:06
Resonance Example
37:29
Draw and Rank Resonance Forms
37:30
Acid-Base Reactions

1h 7m 46s

Intro
0:00
Acid-Base Reactions
0:07
Overview
0:08
Lewis Acid and Lewis Base
0:30
Example 1: Lewis Acid and Lewis Base
1:53
Example 2: Lewis Acid and Lewis Base
3:04
Acid-base Reactions
4:54
Bonsted-Lowry Acid and Bonsted-Lowry Base
4:56
Proton Transfer Reaction
5:36
Acid-Base Equilibrium
8:14
Two Acids in Competition = Equilibrium
8:15
Example: Which is the Stronger Acid?
8:40
Periodic Trends for Acidity
12:40
Across Row
12:41
Periodic Trends for Acidity
19:48
Energy Diagram
19:50
Periodic Trends for Acidity
21:28
Down a Family
21:29
Inductive Effects on Acidity
25:52
Example: Which is the Stronger Acid?
25:54
Other Electron-Withdrawing Group (EWG)
30:37
Inductive Effects on Acidity
32:55
Inductive Effects Decrease with Distance
32:56
Resonance Effects on Acidity
36:35
Examples of Resonance Effects on Acidity
36:36
Resonance Effects on Acidity
41:15
Small and Large Amount of Resonance
41:17
Acid-Base Example
43:10
Which is Most Acidic? Which is the Least Acidic?
43:12
Acid-Base Example
49:26
Which is the Stronger Base?
49:27
Acid-Base Example
53:58
Which is the Strongest Base?
53:59
Common Acids/Bases
1:00:45
Common Acids/Bases
1:00:46
Example: Determine the Direction of Equilibrium
1:04:51
Structures and Properties of Organic Molecules

1h 23m 35s

Intro
0:00
Orbitals and Bonding
0:20
Atomic Orbitals (AO)
0:21
Molecular Orbitals (MO)
1:46
Definition of Molecular Orbitals
1:47
Example 1: Formation of Sigma Bond and Molecular Orbitals
2:20
Molecular Orbitals (MO)
5:25
Example 2: Formation of Pi Bond
5:26
Overlapping E Levels of MO's
7:28
Energy Diagram
7:29
Electronic Transitions
9:18
Electronic Transitions
9:23
Hybrid Orbitals
12:04
Carbon AO
12:06
Hybridization
13:51
Hybrid Orbitals
15:02
Examples of Hybrid Orbitals
15:05
Example: Assign Hybridization
20:31
3-D Sketches
24:05
sp3
24:24
sp2
25:28
sp
27:41
3-D Sketches of Molecules
29:07
3-D Sketches of Molecules 1
29:08
3-D Sketches of Molecules 2
32:29
3-D Sketches of Molecules 3
35:36
3D Sketch
37:20
How to Draw 3D Sketch
37:22
Example 1: Drawing 3D Sketch
37:50
Example 2: Drawing 3D Sketch
43:04
Hybridization and Resonance
46:06
Example: Hybridization and Resonance
46:08
Physical Properties
49:55
Water Solubility, Boiling Points, and Intermolecular Forces
49:56
Types of 'Nonbonding' Interactions
51:47
Dipole-Dipole
52:37
Definition of Dipole-Dipole
52:39
Example: Dipole-Dipole Bonding
53:27
Hydrogen Bonding
57:14
Definition of Hydrogen Bonding
57:15
Example: Hydrogen Bonding
58:05
Van Der Waals/ London Forces
1:03:11
Van Der Waals/ London Forces
1:03:12
Example: Van Der Waals/ London Forces
1:04:59
Water Solubility
1:08:32
Water Solubility
1:08:34
Example: Water Solubility
1:09:05
Example: Acetone
1:11:29
Isomerism
1:13:51
Definition of Isomers
1:13:53
Constitutional Isomers and Example
1:14:17
Stereoisomers and Example
1:15:34
Introduction to Functional Groups
1:17:06
Functional Groups: Example, Abbreviation, and Name
1:17:07
Introduction to Functional Groups
1:20:48
Functional Groups: Example, Abbreviation, and Name
1:20:49
Alkane Structures

1h 13m 38s

Intro
0:00
Nomenclature of Alkanes
0:12
Nomenclature of Alkanes and IUPAC Rules
0:13
Examples: Nomenclature of Alkanes
4:38
Molecular Formula and Degrees of Unsaturation (DU)
17:24
Alkane Formula
17:25
Example: Heptane
17:58
Why '2n+2' Hydrogens?
18:35
Adding a Ring
19:20
Adding a p Bond
19:42
Example 1: Determine Degrees of Unsaturation (DU)
20:17
Example 2: Determine Degrees of Unsaturation (DU)
21:35
Example 3: Determine DU of Benzene
23:30
Molecular Formula and Degrees of Unsaturation (DU)
24:41
Example 4: Draw Isomers
24:42
Physical properties of Alkanes
29:17
Physical properties of Alkanes
29:18
Conformations of Alkanes
33:40
Conformational Isomers
33:42
Conformations of Ethane: Eclipsed and Staggered
34:40
Newman Projection of Ethane
36:15
Conformations of Ethane
40:38
Energy and Degrees Rotated Diagram
40:41
Conformations of Butane
42:28
Butane
42:29
Newman Projection of Butane
43:35
Conformations of Butane
44:25
Energy and Degrees Rotated Diagram
44:30
Cycloalkanes
51:26
Cyclopropane and Cyclobutane
51:27
Cyclopentane
53:56
Cycloalkanes
54:56
Cyclohexane: Chair, Boat, and Twist Boat Conformations
54:57
Drawing a Cyclohexane Chair
57:58
Drawing a Cyclohexane Chair
57:59
Newman Projection of Cyclohexane
1:02:14
Cyclohexane Chair Flips
1:04:06
Axial and Equatorial Groups
1:04:10
Example: Chair Flip on Methylcyclohexane
1:06:44
Cyclohexane Conformations Example
1:09:01
Chair Conformations of cis-1-t-butyl-4-methylcyclohexane
1:09:02
Stereochemistry

1h 40m 54s

Intro
0:00
Stereochemistry
0:10
Isomers
0:11
Stereoisomer Examples
1:30
Alkenes
1:31
Cycloalkanes
2:35
Stereoisomer Examples
4:00
Tetrahedral Carbon: Superimposable (Identical)
4:01
Tetrahedral Carbon: Non-Superimposable (Stereoisomers)
5:18
Chirality
7:18
Stereoisomers
7:19
Chiral
8:05
Achiral
8:29
Example: Achiral and Chiral
8:45
Chirality
20:11
Superimposable, Non-Superimposable, Chiral, and Achiral
20:12
Nomenclature
23:00
Cahn-Ingold-Prelog Rules
23:01
Nomenclature
29:39
Example 1: Nomenclature
29:40
Example 2: Nomenclature
31:49
Example 3: Nomenclature
33:24
Example 4: Nomenclature
35:39
Drawing Stereoisomers
36:58
Drawing (S)-2-bromopentane
36:59
Drawing the Enantiomer of (S)-2-bromopentane: Method 1
38:47
Drawing the Enantiomer of (S)-2-bromopentane: Method 2
39:35
Fischer Projections
41:47
Definition of Fischer Projections
41:49
Drawing Fischer Projection
43:43
Use of Fisher Projection: Assigning Configuration
49:13
Molecules with Two Chiral Carbons
51:49
Example A
51:42
Drawing Enantiomer of Example A
53:26
Fischer Projection of A
54:25
Drawing Stereoisomers, cont.
59:40
Drawing Stereoisomers Examples
59:41
Diastereomers
1:01:48
Drawing Stereoisomers
1:06:37
Draw All Stereoisomers of 2,3-dichlorobutane
1:06:38
Molecules with Two Chiral Centers
1:10:22
Draw All Stereoisomers of 2,3-dichlorobutane, cont.
1:10:23
Optical Activity
1:14:10
Chiral Molecules
1:14:11
Angle of Rotation
1:14:51
Achiral Species
1:16:46
Physical Properties of Stereoisomers
1:17:11
Enantiomers
1:17:12
Diastereomers
1:18:01
Example
1:18:26
Physical Properties of Stereoisomers
1:23:05
When Do Enantiomers Behave Differently?
1:23:06
Racemic Mixtures
1:28:18
Racemic Mixtures
1:28:21
Resolution
1:29:52
Unequal Mixtures of Enantiomers
1:32:54
Enantiomeric Excess (ee)
1:32:55
Unequal Mixture of Enantiomers
1:34:43
Unequal Mixture of Enantiomers
1:34:44
Example: Finding ee
1:36:38
Example: Percent of Composition
1:39:46
Section 2: Understanding Organic Reactions
Nomenclature

1h 53m 47s

Intro
0:00
Cycloalkane Nomenclature
0:17
Cycloalkane Nomenclature and Examples
0:18
Alkene Nomenclature
6:28
Alkene Nomenclature and Examples
6:29
Alkene Nomenclature: Stereochemistry
15:07
Alkenes With Two Groups: Cis & Trans
15:08
Alkenes With Greater Than Two Groups: E & Z
18:26
Alkyne Nomenclature
24:46
Alkyne Nomenclature and Examples
24:47
Alkane Has a Higher Priority Than Alkyne
28:25
Alcohol Nomenclature
29:24
Alcohol Nomenclature and Examples
29:25
Alcohol FG Has Priority Over Alkene/yne
33:41
Ether Nomenclature
36:32
Ether Nomenclature and Examples
36:33
Amine Nomenclature
42:59
Amine Nomenclature and Examples
43:00
Amine Nomenclature
49:45
Primary, Secondary, Tertiary, Quaternary Salt
49:46
Aldehyde Nomenclature
51:37
Aldehyde Nomenclature and Examples
51:38
Ketone Nomenclature
58:43
Ketone Nomenclature and Examples
58:44
Aromatic Nomenclature
1:05:02
Aromatic Nomenclature and Examples
1:05:03
Aromatic Nomenclature, cont.
1:09:09
Ortho, Meta, and Para
1:09:10
Aromatic Nomenclature, cont.
1:13:27
Common Names for Simple Substituted Aromatic Compounds
1:13:28
Carboxylic Acid Nomenclature
1:16:35
Carboxylic Acid Nomenclature and Examples
1:16:36
Carboxylic Acid Derivatives
1:22:28
Carboxylic Acid Derivatives
1:22:42
General Structure
1:23:10
Acid Halide Nomenclature
1:24:48
Acid Halide Nomenclature and Examples
1:24:49
Anhydride Nomenclature
1:28:10
Anhydride Nomenclature and Examples
1:28:11
Ester Nomenclature
1:32:50
Ester Nomenclature
1:32:51
Carboxylate Salts
1:38:51
Amide Nomenclature
1:40:02
Amide Nomenclature and Examples
1:40:03
Nitrile Nomenclature
1:45:22
Nitrile Nomenclature and Examples
1:45:23
Chemical Reactions

51m 1s

Intro
0:00
Chemical Reactions
0:06
Reactants and Products
0:07
Thermodynamics
0:50
Equilibrium Constant
1:06
Equation
2:35
Organic Reaction
3:05
Energy vs. Progress of Rxn Diagrams
3:48
Exothermic Reaction
4:02
Endothermic Reaction
6:54
Estimating ΔH rxn
9:15
Bond Breaking
10:03
Bond Formation
10:25
Bond Strength
11:35
Homolytic Cleavage
11:59
Bond Dissociation Energy (BDE) Table
12:29
BDE for Multiple Bonds
14:32
Examples
17:35
Kinetics
20:35
Kinetics
20:36
Examples
21:49
Reaction Rate Variables
23:15
Reaction Rate Variables
23:16
Increasing Temperature, Increasing Rate
24:08
Increasing Concentration, Increasing Rate
25:39
Decreasing Energy of Activation, Increasing Rate
27:49
Two-Step Mechanisms
30:06
E vs. POR Diagram (2-step Mechanism)
30:07
Reactive Intermediates
33:03
Reactive Intermediates
33:04
Example: A Carbocation
35:20
Carbocation Stability
37:24
Relative Stability of Carbocation
37:25
Alkyl groups and Hyperconjugation
38:45
Carbocation Stability
41:57
Carbocation Stabilized by Resonance: Allylic
41:58
Carbocation Stabilized by Resonance: Benzylic
42:59
Overall Carbocation Stability
44:05
Free Radicals
45:05
Definition and Examples of Free Radicals
45:06
Radical Mechanisms
49:40
Example: Regular Arrow
49:41
Example: Fish-Hook Arrow
50:17
Free Radical Halogenation

26m 23s

Intro
0:00
Free Radical Halogenation
0:06
Free Radical Halogenation
0:07
Mechanism: Initiation
1:27
Mechanism: Propagation Steps
2:21
Free Radical Halogenation
5:33
Termination Steps
5:36
Example 1: Terminations Steps
6:00
Example 2: Terminations Steps
6:18
Example 3: Terminations Steps
7:43
Example 4: Terminations Steps
8:04
Regiochemistry of Free Radical Halogenation
9:32
Which Site/Region Reacts and Why?
9:34
Bromination and Rate of Reaction
14:03
Regiochemistry of Free Radical Halogenation
14:30
Chlorination
14:31
Why the Difference in Selectivity?
19:58
Allylic Halogenation
20:53
Examples of Allylic Halogenation
20:55
Substitution Reactions

1h 48m 5s

Intro
0:00
Substitution Reactions
0:06
Substitution Reactions Example
0:07
Nucleophile
0:39
Electrophile
1:20
Leaving Group
2:56
General Reaction
4:13
Substitution Reactions
4:43
General Reaction
4:46
Substitution Reaction Mechanisms: Simultaneous
5:08
Substitution Reaction Mechanisms: Stepwise
5:34
SN2 Substitution
6:21
Example of SN2 Mechanism
6:22
SN2 Kinetics
7:58
Rate of SN2
9:10
Sterics Affect Rate of SN2
9:12
Rate of SN2 (By Type of RX)
14:13
SN2: E vs. POR Diagram
17:26
E vs. POR Diagram
17:27
Transition State (TS)
18:24
SN2 Transition State, Kinetics
20:58
SN2 Transition State, Kinetics
20:59
Hybridization of TS Carbon
21:57
Example: Allylic LG
23:34
Stereochemistry of SN2
25:46
Backside Attack and Inversion of Stereochemistry
25:48
SN2 Summary
29:56
Summary of SN2
29:58
Predict Products (SN2)
31:42
Example 1: Predict Products
31:50
Example 2: Predict Products
33:38
Example 3: Predict Products
35:11
Example 4: Predict Products
36:11
Example 5: Predict Products
37:32
SN1 Substitution Mechanism
41:52
Is This Substitution? Could This Be an SN2 Mechanism?
41:54
SN1 Mechanism
43:50
Two Key Steps: 1. Loss of LG
43:53
Two Key Steps: 2. Addition of nu
45:11
SN1 Kinetics
47:17
Kinetics of SN1
47:18
Rate of SN1 (By RX type)
48:44
SN1 E vs. POR Diagram
49:49
E vs. POR Diagram
49:51
First Transition Stage (TS-1)
51:48
Second Transition Stage (TS-2)
52:56
Stereochemistry of SN1
53:44
Racemization of SN1 and Achiral Carbocation Intermediate
53:46
Example
54:29
SN1 Summary
58:25
Summary of SN1
58:26
SN1 or SN2 Mechanisms?
1:00:40
Example 1: SN1 or SN2 Mechanisms
1:00:42
Example 2: SN1 or SN2 Mechanisms
1:03:00
Example 3: SN1 or SN2 Mechanisms
1:04:06
Example 4: SN1 or SN2 Mechanisms
1:06:17
SN1 Mechanism
1:09:12
Three Steps of SN1 Mechanism
1:09:13
SN1 Carbocation Rearrangements
1:14:50
Carbocation Rearrangements Example
1:14:51
SN1 Carbocation Rearrangements
1:20:46
Alkyl Groups Can Also Shift
1:20:48
Leaving Groups
1:24:26
Leaving Groups
1:24:27
Forward or Reverse Reaction Favored?
1:26:00
Leaving Groups
1:29:59
Making poor LG Better: Method 1
1:30:00
Leaving Groups
1:34:18
Making poor LG Better: Tosylate (Method 2)
1:34:19
Synthesis Problem
1:38:15
Example: Provide the Necessary Reagents
1:38:16
Nucleophilicity
1:41:10
What Makes a Good Nucleophile?
1:41:11
Nucleophilicity
1:44:45
Periodic Trends: Across Row
1:44:47
Periodic Trends: Down a Family
1:46:46
Elimination Reactions

1h 11m 43s

Intro
0:00
Elimination Reactions: E2 Mechanism
0:06
E2 Mechanism
0:08
Example of E2 Mechanism
1:01
Stereochemistry of E2
4:48
Anti-Coplanar & Anti-Elimination
4:50
Example 1: Stereochemistry of E2
5:34
Example 2: Stereochemistry of E2
10:39
Regiochemistry of E2
13:04
Refiochemistry of E2 and Zaitsev's Rule
13:05
Alkene Stability
17:39
Alkene Stability
19:20
Alkene Stability Examples
19:22
Example 1: Draw Both E2 Products and Select Major
21:57
Example 2: Draw Both E2 Products and Select Major
25:02
SN2 Vs. E2 Mechanisms
29:06
SN2 Vs. E2 Mechanisms
29:07
When Do They Compete?
30:34
SN2 Vs. E2 Mechanisms
31:23
Compare Rates
31:24
SN2 Vs. E2 Mechanisms
36:34
t-BuBr: What If Vary Base?
36:35
Preference for E2 Over SN2 (By RX Type)
40:42
E1 Elimination Mechanism
41:51
E1 - Elimination Unimolecular
41:52
E1 Mechanism: Step 1
44:14
E1 Mechanism: Step 2
44:48
E1 Kinetics
46:58
Rate = k[RCI]
47:00
E1 Rate (By Type of Carbon Bearing LG)
48:31
E1 Stereochemistry
49:49
Example 1: E1 Stereochemistry
49:51
Example 2: E1 Stereochemistry
52:31
Carbocation Rearrangements
55:57
Carbocation Rearrangements
56:01
Product Mixtures
57:20
Predict the Product: SN2 vs. E2
59:58
Example 1: Predict the Product
1:00:00
Example 2: Predict the Product
1:02:10
Example 3: Predict the Product
1:04:07
Predict the Product: SN2 vs. E2
1:06:06
Example 4: Predict the Product
1:06:07
Example 5: Predict the Product
1:07:29
Example 6: Predict the Product
1:07:51
Example 7: Predict the Product
1:09:18
Section 3: Alkanes, Alkenes, & Alkynes
Alkenes

36m 39s

Intro
0:00
Alkenes
0:12
Definition and Structure of Alkenes
0:13
3D Sketch of Alkenes
1:53
Pi Bonds
3:48
Alkene Stability
4:57
Alkyl Groups Attached
4:58
Trans & Cis
6:20
Alkene Stability
8:42
Pi Bonds & Conjugation
8:43
Bridgehead Carbons & Bredt's Rule
10:22
Measuring Stability: Hydrogenation Reaction
11:40
Alkene Synthesis
12:01
Method 1: E2 on Alkyl Halides
12:02
Review: Stereochemistry
16:17
Review: Regiochemistry
16:50
Review: SN2 vs. E2
17:34
Alkene Synthesis
18:57
Method 2: Dehydration of Alcohols
18:58
Mechanism
20:08
Alkene Synthesis
23:26
Alcohol Dehydration
23:27
Example 1: Comparing Strong Acids
26:59
Example 2: Mechanism for Dehydration Reaction
29:00
Example 3: Transform
32:50
Reactions of Alkenes

2h 8m 44s

Intro
0:00
Reactions of Alkenes
0:05
Electrophilic Addition Reaction
0:06
Addition of HX
2:02
Example: Regioselectivity & 2 Steps Mechanism
2:03
Markovnikov Addition
5:30
Markovnikov Addition is Favored
5:31
Graph: E vs. POR
6:33
Example
8:29
Example: Predict and Consider the Stereochemistry
8:30
Hydration of Alkenes
12:31
Acid-catalyzed Addition of Water
12:32
Strong Acid
14:20
Hydration of Alkenes
15:20
Acid-catalyzed Addition of Water: Mechanism
15:21
Hydration vs. Dehydration
19:51
Hydration Mechanism is Exact Reverse of Dehydration
19:52
Example
21:28
Example: Hydration Reaction
21:29
Alternative 'Hydration' Methods
25:26
Oxymercuration-Demercuration
25:27
Oxymercuration Mechanism
28:55
Mechanism of Oxymercuration
28:56
Alternative 'Hydration' Methods
30:51
Hydroboration-Oxidation
30:52
Hydroboration Mechanism
33:22
1-step (concerted)
33:23
Regioselective
34:45
Stereoselective
35:30
Example
35:58
Example: Hydroboration-Oxidation
35:59
Example
40:42
Example: Predict the Major Product
40:43
Synthetic Utility of 'Alternate' Hydration Methods
44:36
Example: Synthetic Utility of 'Alternate' Hydration Methods
44:37
Flashcards
47:28
Tips On Using Flashcards
47:29
Bromination of Alkenes
49:51
Anti-Addition of Br₂
49:52
Bromination Mechanism
53:16
Mechanism of Bromination
53:17
Bromination Mechanism
55:42
Mechanism of Bromination
55:43
Bromination: Halohydrin Formation
58:54
Addition of other Nu: to Bromonium Ion
58:55
Mechanism
1:00:08
Halohydrin: Regiochemistry
1:03:55
Halohydrin: Regiochemistry
1:03:56
Bromonium Ion Intermediate
1:04:26
Example
1:09:28
Example: Predict Major Product
1:09:29
Example Cont.
1:10:59
Example: Predict Major Product Cont.
1:11:00
Catalytic Hydrogenation of Alkenes
1:13:19
Features of Catalytic Hydrogenation
1:13:20
Catalytic Hydrogenation of Alkenes
1:14:48
Metal Surface
1:14:49
Heterogeneous Catalysts
1:15:29
Homogeneous Catalysts
1:16:08
Catalytic Hydrogenation of Alkenes
1:17:44
Hydrogenation & Pi Bond Stability
1:17:45
Energy Diagram
1:19:22
Catalytic Hydrogenation of Dienes
1:20:40
Hydrogenation & Pi Bond Stability
1:20:41
Energy Diagram
1:23:31
Example
1:24:14
Example: Predict Product
1:24:15
Oxidation of Alkenes
1:27:21
Redox Review
1:27:22
Epoxide
1:30:26
Diol (Glycol)
1:30:54
Ketone/ Aldehyde
1:31:13
Epoxidation
1:32:08
Epoxidation
1:32:09
General Mechanism
1:36:32
Alternate Epoxide Synthesis
1:37:38
Alternate Epoxide Synthesis
1:37:39
Dihydroxylation
1:41:10
Dihydroxylation
1:41:12
General Mechanism (Concerted Via Cycle Intermediate)
1:42:38
Ozonolysis
1:44:22
Ozonolysis: Introduction
1:44:23
Ozonolysis: Is It Good or Bad?
1:45:05
Ozonolysis Reaction
1:48:54
Examples
1:51:10
Example 1: Ozonolysis
1:51:11
Example
1:53:25
Radical Addition to Alkenes
1:55:05
Recall: Free-Radical Halogenation
1:55:15
Radical Mechanism
1:55:45
Propagation Steps
1:58:01
Atom Abstraction
1:58:30
Addition to Alkene
1:59:11
Radical Addition to Alkenes
1:59:54
Markovnivok (Electrophilic Addition) & anti-Mark. (Radical Addition)
1:59:55
Mechanism
2:01:03
Alkene Polymerization
2:05:35
Example: Alkene Polymerization
2:05:36
Alkynes

1h 13m 19s

Intro
0:00
Structure of Alkynes
0:04
Structure of Alkynes
0:05
3D Sketch
2:30
Internal and Terminal
4:03
Reductions of Alkynes
4:36
Catalytic Hydrogenation
4:37
Lindlar Catalyst
5:25
Reductions of Alkynes
7:24
Dissolving Metal Reduction
7:25
Oxidation of Alkynes
9:24
Ozonolysis
9:25
Reactions of Alkynes
10:56
Addition Reactions: Bromination
10:57
Addition of HX
12:24
Addition of HX
12:25
Addition of HX
13:36
Addition of HX: Mechanism
13:37
Example
17:38
Example: Transform
17:39
Hydration of Alkynes
23:35
Hydration of Alkynes
23:36
Hydration of Alkynes
26:47
Hydration of Alkynes: Mechanism
26:49
'Hydration' via Hydroboration-Oxidation
32:57
'Hydration' via Hydroboration-Oxidation
32:58
Disiamylborane
33:28
Hydroboration-Oxidation Cont.
34:25
Alkyne Synthesis
36:17
Method 1: Alkyne Synthesis By Dehydrohalogenation
36:19
Alkyne Synthesis
39:06
Example: Transform
39:07
Alkyne Synthesis
41:21
Method 2 & Acidity of Alkynes
41:22
Conjugate Bases
43:06
Preparation of Acetylide Anions
49:55
Preparation of Acetylide Anions
49:57
Alkyne Synthesis
53:40
Synthesis Using Acetylide Anions
53:41
Example 1: Transform
57:04
Example 2: Transform
1:01:07
Example 3: Transform
1:06:22
Section 4: Alcohols
Alcohols, Part I

59m 52s

Intro
0:00
Alcohols
0:11
Attributes of Alcohols
0:12
Boiling Points
2:00
Water Solubility
5:00
Water Solubility (Like Dissolves Like)
5:01
Acidity of Alcohols
9:39
Comparison of Alcohols Acidity
9:41
Preparation of Alkoxides
13:03
Using Strong Base Like Sodium Hydride
13:04
Using Redox Reaction
15:36
Preparation of Alkoxides
17:41
Using K°
17:42
Phenols Are More Acidic Than Other Alcohols
19:51
Synthesis of Alcohols, ROH
21:43
Synthesis of Alcohols from Alkyl Halides, RX (SN2 or SN1)
21:44
Synthesis of Alcohols, ROH
25:08
Unlikely on 2° RX (E2 Favored)
25:09
Impossible on 3° RX (E2) and Phenyl/Vinyl RX (N/R)
25:47
Synthesis of Alcohols, ROH
26:26
SN1 with H₂O 'Solvolysis' or 'Hydrolysis'
26:27
Carbocation Can Rearrange
29:00
Synthesis of Alcohols, ROH
30:08
Synthesis of Alcohols From Alkenes: Hydration
30:09
Synthesis of Alcohols From Alkenes: Oxidation/Diol
32:20
Synthesis of Alcohols, ROH
33:14
Synthesis of Alcohols From Ketones and Aldehydes
33:15
Organometallic Reagents: Preparation
37:03
Grignard (RMgX)
37:04
Organolithium (Rli)
40:03
Organometallic Reagents: Reactions
41:45
Reactions of Organometallic Reagents
41:46
Organometallic Reagents: Reactions as Strong Nu:
46:40
Example 1: Reactions as Strong Nu:
46:41
Example 2: Reactions as Strong Nu:
48:57
Hydride Nu:
50:52
Hydride Nu:
50:53
Examples
53:34
Predict 1
53:35
Predict 2
54:45
Examples
56:43
Transform
56:44
Provide Starting Material
58:18
Alcohols, Part II

45m 35s

Intro
0:00
Oxidation Reactions
0:08
Oxidizing Agents: Jones, PCC, Swern
0:09
'Jones' Oxidation
0:43
Example 1: Predict Oxidation Reactions
2:29
Example 2: Predict Oxidation Reactions
3:00
Oxidation Reactions
4:11
Selective Oxidizing Agents (PCC and Swern)
4:12
PCC (Pyridiniym Chlorochromate)
5:10
Swern Oxidation
6:05
General [ox] Mechanism
8:32
General [ox] Mechanism
8:33
Oxidation of Alcohols
10:11
Example 1: Oxidation of Alcohols
10:12
Example 2: Oxidation of Alcohols
11:20
Example 3: Oxidation of Alcohols
11:46
Example
13:09
Predict: PCC Oxidation Reactions
13:10
Tosylation of Alcohols
15:22
Introduction to Tosylation of Alcohols
15:23
Example
21:08
Example: Tosylation of Alcohols
21:09
Reductions of Alcohols
23:39
Reductions of Alcohols via SN2 with Hydride
24:22
Reductions of Alcohols via Dehydration
27:12
Conversion of Alcohols to Alkyl Halides
30:12
Conversion of Alcohols to Alkyl Halides via Tosylate
30:13
Conversion of Alcohols to Alkyl Halides
31:17
Using HX
31:18
Mechanism
32:09
Conversion of Alcohols to Alkyl Halides
35:43
Reagents that Provide LG and Nu: in One 'Pot'
35:44
General Mechanisms
37:44
Example 1: General Mechanisms
37:45
Example 2: General Mechanisms
39:25
Example
41:04
Transformation of Alcohols
41:05
Section 5: Ethers, Thiols, Thioethers, & Ketones
Ethers

1h 34m 45s

Intro
0:00
Ethers
0:11
Overview of Ethers
0:12
Boiling Points
1:37
Ethers
4:34
Water Solubility (Grams per 100mL H₂O)
4:35
Synthesis of Ethers
7:53
Williamson Ether Synthesis
7:54
Example: Synthesis of Ethers
9:23
Synthesis of Ethers
10:27
Example: Synthesis of Ethers
10:28
Intramolecular SN2
13:04
Planning an Ether Synthesis
14:45
Example 1: Planning an Ether Synthesis
14:46
Planning an Ether Synthesis
16:16
Example 2: Planning an Ether Synthesis
16:17
Planning an Ether Synthesis
22:04
Example 3: Synthesize Dipropyl Ether
22:05
Planning an Ether Synthesis
26:01
Example 4: Transform
26:02
Synthesis of Epoxides
30:05
Synthesis of Epoxides Via Williamson Ether Synthesis
30:06
Synthesis of Epoxides Via Oxidation
32:42
Reaction of Ethers
33:35
Reaction of Ethers
33:36
Reactions of Ethers with HBr or HI
34:44
Reactions of Ethers with HBr or HI
34:45
Mechanism
35:25
Epoxide Ring-Opening Reaction
39:25
Epoxide Ring-Opening Reaction
39:26
Example: Epoxide Ring-Opening Reaction
42:42
Acid-Catalyzed Epoxide Ring Opening
44:16
Acid-Catalyzed Epoxide Ring Opening Mechanism
44:17
Acid-Catalyzed Epoxide Ring Opening
50:13
Acid-Catalyzed Epoxide Ring Opening Mechanism
50:14
Catalyst Needed for Ring Opening
53:34
Catalyst Needed for Ring Opening
53:35
Stereochemistry of Epoxide Ring Opening
55:56
Stereochemistry: SN2 Mechanism
55:57
Acid or Base Mechanism?
58:30
Example
1:01:03
Transformation
1:01:04
Regiochemistry of Epoxide Ring Openings
1:05:29
Regiochemistry of Epoxide Ring Openings in Base
1:05:30
Regiochemistry of Epoxide Ring Openings in Acid
1:07:34
Example
1:10:26
Example 1: Epoxide Ring Openings in Base
1:10:27
Example 2: Epoxide Ring Openings in Acid
1:12:50
Reactions of Epoxides with Grignard and Hydride
1:15:35
Reactions of Epoxides with Grignard and Hydride
1:15:36
Example
1:21:47
Example: Ethers
1:21:50
Example
1:27:01
Example: Synthesize
1:27:02
Thiols and Thioethers

16m 50s

Intro
0:00
Thiols and Thioethers
0:10
Physical Properties
0:11
Reactions Can Be Oxidized
2:16
Acidity of Thiols
3:11
Thiols Are More Acidic Than Alcohols
3:12
Synthesis of Thioethers
6:44
Synthesis of Thioethers
6:45
Example
8:43
Example: Synthesize the Following Target Molecule
8:44
Example
14:18
Example: Predict
14:19
Ketones

2h 18m 12s

Intro
0:00
Aldehydes & Ketones
0:11
The Carbonyl: Resonance & Inductive
0:12
Reactivity
0:50
The Carbonyl
2:35
The Carbonyl
2:36
Carbonyl FG's
4:10
Preparation/Synthesis of Aldehydes & Ketones
6:18
Oxidation of Alcohols
6:19
Ozonolysis of Alkenes
7:16
Hydration of Alkynes
8:01
Reaction with Hydride Nu:
9:00
Reaction with Hydride Nu:
9:01
Reaction with Carbon Nu:
11:29
Carbanions: Acetylide
11:30
Carbanions: Cyanide
14:23
Reaction with Carbon Nu:
15:32
Organometallic Reagents (RMgX, Rli)
15:33
Retrosynthesis of Alcohols
17:04
Retrosynthesis of Alcohols
17:05
Example
19:30
Example: Transform
19:31
Example
22:57
Example: Transform
22:58
Example
28:19
Example: Transform
28:20
Example
33:36
Example: Transform
33:37
Wittig Reaction
37:39
Wittig Reaction: A Resonance-Stabilized Carbanion (Nu:)
37:40
Wittig Reaction: Mechanism
39:51
Preparation of Wittig Reagent
41:58
Two Steps From RX
41:59
Example: Predict
45:02
Wittig Retrosynthesis
46:19
Wittig Retrosynthesis
46:20
Synthesis
48:09
Reaction with Oxygen Nu:
51:21
Addition of H₂O
51:22
Exception: Formaldehyde is 99% Hydrate in H₂O Solution
54:10
Exception: Hydrate is Favored if Partial Positive Near Carbonyl
55:26
Reaction with Oxygen Nu:
57:45
Addition of ROH
57:46
TsOH: Tosic Acid
58:28
Addition of ROH Cont.
59:09
Example
1:01:43
Predict
1:01:44
Mechanism
1:03:08
Mechanism for Acetal Formation
1:04:10
Mechanism for Acetal Formation
1:04:11
What is a CTI?
1:15:04
Tetrahedral Intermediate
1:15:05
Charged Tetrahedral Intermediate
1:15:45
CTI: Acid-cat
1:16:10
CTI: Base-cat
1:17:01
Acetals & Cyclic Acetals
1:17:49
Overall
1:17:50
Cyclic Acetals
1:18:46
Hydrolysis of Acetals: Regenerates Carbonyl
1:20:01
Hydrolysis of Acetals: Regenerates Carbonyl
1:20:02
Mechanism
1:22:08
Reaction with Nitrogen Nu:
1:30:11
Reaction with Nitrogen Nu:
1:30:12
Example
1:32:18
Mechanism of Imine Formation
1:33:24
Mechanism of Imine Formation
1:33:25
Oxidation of Aldehydes
1:38:12
Oxidation of Aldehydes 1
1:38:13
Oxidation of Aldehydes 2
1:39:52
Oxidation of Aldehydes 3
1:40:10
Reductions of Ketones and Aldehydes
1:40:54
Reductions of Ketones and Aldehydes
1:40:55
Hydride/ Workup
1:41:22
Raney Nickel
1:42:07
Reductions of Ketones and Aldehydes
1:43:24
Clemmensen Reduction & Wolff-Kishner Reduction
1:43:40
Acetals as Protective Groups
1:46:50
Acetals as Protective Groups
1:46:51
Example
1:50:39
Example: Consider the Following Synthesis
1:50:40
Protective Groups
1:54:47
Protective Groups
1:54:48
Example
1:59:02
Example: Transform
1:59:03
Example: Another Route
2:04:54
Example: Transform
2:08:49
Example
2:08:50
Transform
2:08:51
Example
2:11:05
Transform
2:11:06
Example
2:13:45
Transform
2:13:46
Example
2:15:43
Provide the Missing Starting Material
2:15:44
Section 6: Organic Transformation Practice
Transformation Practice Problems

38m 58s

Intro
0:00
Practice Problems
0:33
Practice Problem 1: Transform
0:34
Practice Problem 2: Transform
3:57
Practice Problems
7:49
Practice Problem 3: Transform
7:50
Practice Problems
15:32
Practice Problem 4: Transform
15:34
Practice Problem 5: Transform
20:15
Practice Problems
24:08
Practice Problem 6: Transform
24:09
Practice Problem 7: Transform
29:27
Practice Problems
33:08
Practice Problem 8: Transform
33:09
Practice Problem 9: Transform
35:23
Section 7: Carboxylic Acids
Carboxylic Acids

1h 17m 51s

Intro
0:00
Review Reactions of Ketone/Aldehyde
0:06
Carbonyl Reactivity
0:07
Nu: = Hydride (Reduction)
1:37
Nu: = Grignard
2:08
Review Reactions of Ketone/Aldehyde
2:53
Nu: = Alcohol
2:54
Nu: = Amine
3:46
Carboxylic Acids and Their Derivatives
4:37
Carboxylic Acids and Their Derivatives
4:38
Ketone vs. Ester Reactivity
6:33
Ketone Reactivity
6:34
Ester Reactivity
6:55
Carboxylic Acids and Their Derivatives
7:30
Acid Halide, Anhydride, Ester, Amide, and Nitrile
7:43
General Reactions of Acarboxylic Acid Derivatives
9:22
General Reactions of Acarboxylic Acid Derivatives
9:23
Physical Properties of Carboxylic Acids
12:16
Acetic Acid
12:17
Carboxylic Acids
15:46
Aciditiy of Carboxylic Acids, RCO₂H
17:45
Alcohol
17:46
Carboxylic Acid
19:21
Aciditiy of Carboxylic Acids, RCO₂H
21:31
Aciditiy of Carboxylic Acids, RCO₂H
21:32
Aciditiy of Carboxylic Acids, RCO₂H
24:48
Example: Which is the Stronger Acid?
24:49
Aciditiy of Carboxylic Acids, RCO₂H
30:06
Inductive Effects Decrease with Distance
30:07
Preparation of Carboxylic Acids, RCO₂H
31:55
A) By Oxidation
31:56
Preparation of Carboxylic Acids, RCO₂H
34:37
Oxidation of Alkenes/Alkynes - Ozonolysis
34:38
Preparation of Carboxylic Acids, RCO₂H
36:17
B) Preparation of RCO₂H from Organometallic Reagents
36:18
Preparation of Carboxylic Acids, RCO₂H
38:02
Example: Preparation of Carboxylic Acids
38:03
Preparation of Carboxylic Acids, RCO₂H
40:38
C) Preparation of RCO₂H by Hydrolysis of Carboxylic Acid Derivatives
40:39
Hydrolysis Mechanism
42:19
Hydrolysis Mechanism
42:20
Mechanism: Acyl Substitution (Addition/Elimination)
43:05
Hydrolysis Mechanism
47:27
Substitution Reaction
47:28
RO is Bad LG for SN1/SN2
47:39
RO is okay LG for Collapse of CTI
48:31
Hydrolysis Mechanism
50:07
Base-promoted Ester Hydrolysis (Saponification)
50:08
Applications of Carboxylic Acid Derivatives:
53:10
Saponification Reaction
53:11
Ester Hydrolysis
57:15
Acid-Catalyzed Mechanism
57:16
Ester Hydrolysis Requires Acide or Base
1:03:06
Ester Hydrolysis Requires Acide or Base
1:03:07
Nitrile Hydrolysis
1:05:22
Nitrile Hydrolysis
1:05:23
Nitrile Hydrolysis Mechanism
1:06:53
Nitrile Hydrolysis Mechanism
1:06:54
Use of Nitriles in Synthesis
1:12:39
Example: Nitirles in Synthesis
1:12:40
Carboxylic Acid Derivatives

1h 21m 4s

Intro
0:00
Carboxylic Acid Derivatives
0:05
Carboxylic Acid Derivatives
0:06
General Structure
1:00
Preparation of Carboxylic Acid Derivatives
1:19
Which Carbonyl is the Better E+?
1:20
Inductive Effects
1:54
Resonance
3:23
Preparation of Carboxylic Acid Derivatives
6:52
Which is Better E+, Ester or Acid Chloride?
6:53
Inductive Effects
7:02
Resonance
7:20
Preparation of Carboxylic Acid Derivatives
10:45
Which is Better E+, Carboxylic Acid or Anhydride?
10:46
Inductive Effects & Resonance
11:00
Overall: Order of Electrophilicity and Leaving Group
14:49
Order of Electrophilicity and Leaving Group
14:50
Example: Acid Chloride
16:26
Example: Carboxylate
19:17
Carboxylic Acid Derivative Interconversion
20:53
Carboxylic Acid Derivative Interconversion
20:54
Preparation of Acid Halides
24:31
Preparation of Acid Halides
24:32
Preparation of Anhydrides
25:45
A) Dehydration of Acids (For Symmetrical Anhydride)
25:46
Preparation of Anhydrides
27:29
Example: Dehydration of Acids
27:30
Preparation of Anhydrides
29:16
B) From an Acid Chloride (To Make Mixed Anhydride)
29:17
Mechanism
30:03
Preparation of Esters
31:53
A) From Acid Chloride or Anhydride
31:54
Preparation of Esters
33:48
B) From Carboxylic Acids (Fischer Esterification)
33:49
Mechanism
36:55
Preparations of Esters
41:38
Example: Predict the Product
41:39
Preparation of Esters
43:17
C) Transesterification
43:18
Mechanism
45:17
Preparation of Esters
47:58
D) SN2 with Carboxylate
47:59
Mechanism: Diazomethane
49:28
Preparation of Esters
51:01
Example: Transform
51:02
Preparation of Amides
52:27
A) From an Acid Cl or Anhydride
52:28
Preparations of Amides
54:47
B) Partial Hydrolysis of Nitriles
54:48
Preparation of Amides
56:11
Preparation of Amides: Find Alternate Path
56:12
Preparation of Amides
59:04
C) Can't be Easily Prepared from RCO₂H Directly
59:05
Reactions of Carboxylic Acid Derivatives with Nucleophiles
1:01:41
A) Hydride Nu: Review
1:01:42
A) Hydride Nu: Sodium Borohydride + Ester
1:02:43
Reactions of Carboxylic Acid Derivatives with Nucleophiles
1:03:57
Lithium Aluminum Hydride (LAH)
1:03:58
Mechanism
1:04:29
Summary of Hydride Reductions
1:07:09
Summary of Hydride Reductions 1
1:07:10
Summary of Hydride Reductions 2
1:07:36
Hydride Reduction of Amides
1:08:12
Hydride Reduction of Amides Mechanism
1:08:13
Reaction of Carboxylic Acid Derivatives with Organometallics
1:12:04
Review 1
1:12:05
Review 2
1:12:50
Reaction of Carboxylic Acid Derivatives with Organometallics
1:14:22
Example: Lactone
1:14:23
Special Hydride Nu: Reagents
1:16:34
Diisobutylaluminum Hydride
1:16:35
Example
1:17:25
Other Special Hydride
1:18:41
Addition of Organocuprates to Acid Chlorides
1:19:07
Addition of Organocuprates to Acid Chlorides
1:19:08
Section 8: Enols & Enolates
Enols and Enolates, Part 1

1h 26m 22s

Intro
0:00
Enols and Enolates
0:09
The Carbonyl
0:10
Keto-Enol Tautomerization
1:17
Keto-Enol Tautomerization Mechanism
2:28
Tautomerization Mechanism (2 Steps)
2:29
Keto-Enol Tautomerization Mechanism
5:15
Reverse Reaction
5:16
Mechanism
6:07
Formation of Enolates
7:27
Why is a Ketone's α H's Acidic?
7:28
Formation of Other Carbanions
10:05
Alkyne
10:06
Alkane and Alkene
10:53
Formation of an Enolate: Choice of Base
11:27
Example: Choice of Base
11:28
Formation of an Enolate: Choice of Base
13:56
Deprotonate, Stronger Base, and Lithium Diisopropyl Amide (LDA)
13:57
Formation of an Enolate: Choice of Base
15:48
Weaker Base & 'Active' Methylenes
15:49
Why Use NaOEt instead of NaOH?
19:01
Other Acidic 'α' Protons
20:30
Other Acidic 'α' Protons
20:31
Why is an Ester Less Acidic than a Ketone?
24:10
Other Acidic 'α' Protons
25:19
Other Acidic 'α' Protons Continue
25:20
How are Enolates Used
25:54
Enolates
25:55
Possible Electrophiles
26:21
Alkylation of Enolates
27:56
Alkylation of Enolates
27:57
Resonance Form
30:03
α-Halogenation
32:17
α-Halogenation
32:18
Iodoform Test for Methyl Ketones
33:47
α-Halogenation
35:55
Acid-Catalyzed
35:57
Mechanism: 1st Make Enol (2 Steps)
36:14
Whate Other Eloctrophiles ?
39:17
Aldol Condensation
39:38
Aldol Condensation
39:39
Aldol Mechanism
41:26
Aldol Mechanism: In Base, Deprotonate First
41:27
Aldol Mechanism
45:28
Mechanism for Loss of H₂O
45:29
Collapse of CTI and β-elimination Mechanism
47:51
Loss of H₂0 is not E2!
48:39
Aldol Summary
49:53
Aldol Summary
49:54
Base-Catalyzed Mechanism
52:34
Acid-Catalyzed Mechansim
53:01
Acid-Catalyzed Aldol Mechanism
54:01
First Step: Make Enol
54:02
Acid-Catalyzed Aldol Mechanism
56:54
Loss of H₂0 (β elimination)
56:55
Crossed/Mixed Aldol
1:00:55
Crossed/Mixed Aldol & Compound with α H's
1:00:56
Ketone vs. Aldehyde
1:02:30
Crossed/Mixed Aldol & Compound with α H's Continue
1:03:10
Crossed/Mixed Aldol
1:05:21
Mixed Aldol: control Using LDA
1:05:22
Crossed/Mixed Aldol Retrosynthesis
1:08:53
Example: Predic Aldol Starting Material (Aldol Retrosyntheiss)
1:08:54
Claisen Condensation
1:12:54
Claisen Condensation (Aldol on Esters)
1:12:55
Claisen Condensation
1:19:52
Example 1: Claisen Condensation
1:19:53
Claisen Condensation
1:22:48
Example 2: Claisen Condensation
1:22:49
Enols and Enolates, Part 2

50m 57s

Intro
0:00
Conjugate Additions
0:06
α, β-unsaturated Carbonyls
0:07
Conjugate Additions
1:50
'1,2-addition'
1:51
'1,-4-addition' or 'Conjugate Addition'
2:24
Conjugate Additions
4:53
Why can a Nu: Add to this Alkene?
4:54
Typical Alkene
5:09
α, β-unsaturated Alkene
5:39
Electrophilic Alkenes: Michael Acceptors
6:35
Other 'Electrophilic' Alkenes (Called 'Michael Acceptors)
6:36
1,4-Addition of Cuprates (R2CuLi)
8:29
1,4-Addition of Cuprates (R2CuLi)
8:30
1,4-Addition of Cuprates (R2CuLi)
11:23
Use Cuprates in Synthesis
11:24
Preparation of Cuprates
12:25
Prepare Organocuprate From Organolithium
12:26
Cuprates Also Do SN2 with RX E+ (Not True for RMgX, RLi)
13:06
1,4-Addition of Enolates: Michael Reaction
13:50
1,4-Addition of Enolates: Michael Reaction
13:51
Mechanism
15:57
1,4-Addition of Enolates: Michael Reaction
18:47
Example: 1,4-Addition of Enolates
18:48
1,4-Addition of Enolates: Michael Reaction
21:02
Michael Reaction, Followed by Intramolecular Aldol
21:03
Mechanism of the Robinson Annulation
24:26
Mechanism of the Robinson Annulation
24:27
Enols and Enolates: Advanced Synthesis Topics
31:10
Stablized Enolates and the Decarboxylation Reaction
31:11
Mechanism: A Pericyclic Reaction
32:08
Enols and Enolates: Advanced Synthesis Topics
33:32
Example: Advance Synthesis
33:33
Enols and Enolates: Advanced Synthesis Topics
36:10
Common Reagents: Diethyl Malonate
36:11
Common Reagents: Ethyl Acetoacetate
37:27
Enols and Enolates: Advanced Synthesis Topics
38:06
Example: Transform
38:07
Advanced Synthesis Topics: Enamines
41:52
Enamines
41:53
Advanced Synthesis Topics: Enamines
43:06
Reaction with Ketone/Aldehyde
43:07
Example
44:08
Advanced Synthesis Topics: Enamines
45:31
Example: Use Enamines as Nu: (Like Enolate)
45:32
Advanced Synthesis Topics: Enamines
47:56
Example
47:58
Section 9: Aromatic Compounds
Aromatic Compounds: Structure

1h 59s

Intro
0:00
Aromatic Compounds
0:05
Benzene
0:06
3D Sketch
1:33
Features of Benzene
4:41
Features of Benzene
4:42
Aromatic Stability
6:41
Resonance Stabilization of Benzene
6:42
Cyclohexatriene
7:24
Benzene (Actual, Experimental)
8:11
Aromatic Stability
9:03
Energy Graph
9:04
Aromaticity Requirements
9:55
1) Cyclic and Planar
9:56
2) Contiguous p Orbitals
10:49
3) Satisfy Huckel's Rule
11:20
Example: Benzene
12:32
Common Aromatic Compounds
13:28
Example: Pyridine
13:29
Common Aromatic Compounds
16:25
Example: Furan
16:26
Common Aromatic Compounds
19:42
Example: Thiophene
19:43
Example: Pyrrole
20:18
Common Aromatic Compounds
21:09
Cyclopentadienyl Anion
21:10
Cycloheptatrienyl Cation
23:48
Naphthalene
26:04
Determining Aromaticity
27:28
Example: Which of the Following are Aromatic?
27:29
Molecular Orbital (MO) Theory
32:26
What's So Special About '4n + 2' Electrons?
32:27
π bond & Overlapping p Orbitals
32:53
Molecular Orbital (MO) Diagrams
36:56
MO Diagram: Benzene
36:58
Drawing MO Diagrams
44:26
Example: 3-Membered Ring
44:27
Example: 4-Membered Ring
46:04
Drawing MO Diagrams
47:51
Example: 5-Membered Ring
47:52
Example: 8-Membered Ring
49:32
Aromaticity and Reactivity
51:03
Example: Which is More Acidic?
51:04
Aromaticity and Reactivity
56:03
Example: Which has More Basic Nitrogen, Pyrrole or Pyridine?
56:04
Aromatic Compounds: Reactions, Part 1

1h 24m 4s

Intro
0:00
Reactions of Benzene
0:07
N/R as Alkenes
0:08
Substitution Reactions
0:50
Electrophilic Aromatic Substitution
1:24
Electrophilic Aromatic Substitution
1:25
Mechanism Step 1: Addition of Electrophile
2:08
Mechanism Step 2: Loss of H+
4:14
Electrophilic Aromatic Substitution on Substituted Benzenes
5:21
Electron Donating Group
5:22
Electron Withdrawing Group
8:02
Halogen
9:23
Effects of Electron-Donating Groups (EDG)
10:23
Effects of Electron-Donating Groups (EDG)
10:24
What Effect Does EDG (OH) Have?
11:40
Reactivity
13:03
Regioselectivity
14:07
Regioselectivity: EDG is o/p Director
14:57
Prove It! Add E+ and Look at Possible Intermediates
14:58
Is OH Good or Bad?
17:38
Effects of Electron-Withdrawing Groups (EWG)
20:20
What Effect Does EWG Have?
20:21
Reactivity
21:28
Regioselectivity
22:24
Regioselectivity: EWG is a Meta Director
23:23
Prove It! Add E+ and Look at Competing Intermediates
23:24
Carbocation: Good or Bad?
26:01
Effects of Halogens on EAS
28:33
Inductive Withdrawal of e- Density vs. Resonance Donation
28:34
Summary of Substituent Effects on EAS
32:33
Electron Donating Group
32:34
Electron Withdrawing Group
33:37
Directing Power of Substituents
34:35
Directing Power of Substituents
34:36
Example
36:41
Electrophiles for Electrophilic Aromatic Substitution
38:43
Reaction: Halogenation
38:44
Electrophiles for Electrophilic Aromatic Substitution
40:27
Reaction: Nitration
40:28
Electrophiles for Electrophilic Aromatic Substitution
41:45
Reaction: Sulfonation
41:46
Electrophiles for Electrophilic Aromatic Substitution
43:19
Reaction: Friedel-Crafts Alkylation
43:20
Electrophiles for Electrophilic Aromatic Substitution
45:43
Reaction: Friedel-Crafts Acylation
45:44
Electrophilic Aromatic Substitution: Nitration
46:52
Electrophilic Aromatic Substitution: Nitration
46:53
Mechanism
48:56
Nitration of Aniline
52:40
Nitration of Aniline Part 1
52:41
Nitration of Aniline Part 2: Why?
54:12
Nitration of Aniline
56:10
Workaround: Protect Amino Group as an Amide
56:11
Electrophilic Aromatic Substitution: Sulfonation
58:16
Electrophilic Aromatic Substitution: Sulfonation
58:17
Example: Transform
59:25
Electrophilic Aromatic Substitution: Friedel-Crafts Alkylation
1:02:24
Electrophilic Aromatic Substitution: Friedel-Crafts Alkylation
1:02:25
Example & Mechanism
1:03:37
Friedel-Crafts Alkylation Drawbacks
1:05:48
A) Can Over-React (Dialkylation)
1:05:49
Friedel-Crafts Alkylation Drawbacks
1:08:21
B) Carbocation Can Rearrange
1:08:22
Mechanism
1:09:33
Friedel-Crafts Alkylation Drawbacks
1:13:35
Want n-Propyl? Use Friedel-Crafts Acylation
1:13:36
Reducing Agents
1:16:45
Synthesis with Electrophilic Aromatic Substitution
1:18:45
Example: Transform
1:18:46
Synthesis with Electrophilic Aromatic Substitution
1:20:59
Example: Transform
1:21:00
Aromatic Compounds: Reactions, Part 2

59m 10s

Intro
0:00
Reagents for Electrophilic Aromatic Substitution
0:07
Reagents for Electrophilic Aromatic Substitution
0:08
Preparation of Diazonium Salt
2:12
Preparation of Diazonium Salt
2:13
Reagents for Sandmeyer Reactions
4:14
Reagents for Sandmeyer Reactions
4:15
Apply Diazonium Salt in Synthesis
6:20
Example: Transform
6:21
Apply Diazonium Salt in Synthesis
9:14
Example: Synthesize Following Target Molecule from Benzene or Toluene
9:15
Apply Diazonium Salt in Synthesis
14:56
Example: Transform
14:57
Reactions of Aromatic Substituents
21:56
A) Reduction Reactions
21:57
Reactions of Aromatic Substituents
23:24
B) Oxidations of Arenes
23:25
Benzylic [ox] Even Breaks C-C Bonds!
25:05
Benzylic Carbon Can't Be Quaternary
25:55
Reactions of Aromatic Substituents
26:21
Example
26:22
Review of Benzoic Acid Synthesis
27:34
Via Hydrolysis
27:35
Via Grignard
28:20
Reactions of Aromatic Substituents
29:15
C) Benzylic Halogenation
29:16
Radical Stabilities
31:55
N-bromosuccinimide (NBS)
32:23
Reactions of Aromatic Substituents
33:08
D) Benzylic Substitutions
33:09
Reactions of Aromatic Side Chains
37:08
Example: Transform
37:09
Nucleophilic Aromatic Substitution
43:13
Nucleophilic Aromatic Substitution
43:14
Nucleophilic Aromatic Substitution
47:08
Example
47:09
Mechanism
48:00
Nucleophilic Aromatic Substitution
50:43
Example
50:44
Nucleophilic Substitution: Benzyne Mechanism
52:46
Nucleophilic Substitution: Benzyne Mechanism
52:47
Nucleophilic Substitution: Benzyne Mechanism
57:31
Example: Predict Product
57:32
Section 10: Dienes & Amines
Conjugated Dienes

1h 9m 12s

Intro
0:00
Conjugated Dienes
0:08
Conjugated π Bonds
0:09
Diene Stability
2:00
Diene Stability: Cumulated
2:01
Diene Stability: Isolated
2:37
Diene Stability: Conjugated
2:51
Heat of Hydrogenation
3:00
Allylic Carbocations and Radicals
5:15
Allylic Carbocations and Radicals
5:16
Electrophilic Additions to Dienes
7:00
Alkenes
7:01
Unsaturated Ketone
7:47
Electrophilic Additions to Dienes
8:28
Conjugated Dienes
8:29
Electrophilic Additions to Dienes
9:46
Mechanism (2-Steps): Alkene
9:47
Electrophilic Additions to Dienes
11:40
Mechanism (2-Steps): Diene
11:41
1,2 'Kinetic' Product
13:08
1,4 'Thermodynamic' Product
14:47
E vs. POR Diagram
15:50
E vs. POR Diagram
15:51
Kinetic vs. Thermodynamic Control
21:56
Kinetic vs. Thermodynamic Control
21:57
How? Reaction is Reversible!
23:51
1,2 (Less Stable product)
23:52
1,4 (More Stable Product)
25:16
Diels Alder Reaction
26:34
Diels Alder Reaction
26:35
Dienophiles (E+)
29:23
Dienophiles (E+)
29:24
Alkyne Diels-Alder Example
30:48
Example: Alkyne Diels-Alder
30:49
Diels-Alder Reaction: Dienes (Nu:)
32:22
Diels-Alder ReactionL Dienes (Nu:)
32:23
Diels-Alder Reaction: Dienes
33:51
Dienes Must Have 's-cis' Conformation
33:52
Example
35:25
Diels-Alder Reaction with Cyclic Dienes
36:08
Cyclic Dienes are Great for Diels-Alder Reaction
36:09
Cyclopentadiene
37:10
Diels-Alder Reaction: Bicyclic Products
40:50
Endo vs. Exo Terminology: Norbornane & Bicyclo Heptane
40:51
Example: Bicyclo Heptane
42:29
Diels-Alder Reaction with Cyclic Dienes
44:15
Example
44:16
Stereochemistry of the Diels-Alder Reaction
47:39
Stereochemistry of the Diels-Alder Reaction
47:40
Example
48:08
Stereochemistry of the Diels-Alder Reaction
50:21
Example
50:22
Regiochemistry of the Diels-Alder Reaction
52:42
Rule: 1,2-Product Preferred Over 1,3-Product
52:43
Regiochemistry of the Diels-Alder Reaction
54:18
Rule: 1,4-Product Preferred Over 1,3-Product
54:19
Regiochemistry of the Diels-Alder Reaction
55:02
Why 1,2-Product or 1,4-Product Favored?
55:03
Example
56:11
Diels-Alder Reaction
58:06
Example: Predict
58:07
Diels-Alder Reaction
1:01:27
Explain Why No Diels-Alder Reaction Takes Place in This Case
1:01:28
Diels-Alder Reaction
1:03:09
Example: Predict
1:03:10
Diels-Alder Reaction: Synthesis Problem
1:05:39
Diels-Alder Reaction: Synthesis Problem
1:05:40
Pericyclic Reactions and Molecular Orbital (MO) Theory

1h 21m 31s

Intro
0:00
Pericyclic Reactions
0:05
Pericyclic Reactions
0:06
Electrocyclic Reactions
1:19
Electrocyclic Reactions
1:20
Electrocyclic Reactions
3:13
Stereoselectivity
3:14
Electrocyclic Reactions
8:10
Example: Predict
8:11
Sigmatropic Rearrangements
12:29
Sigmatropic Rearrangements
12:30
Cope Rearrangement
14:44
Sigmatropic Rearrangements
16:44
Claisen Rearrangement 1
16:45
Claisen Rearrangement 2
17:46
Cycloaddition Reactions
19:22
Diels-Alder
19:23
1,3-Dipolar Cycloaddition
20:32
Cycloaddition Reactions: Stereochemistry
21:58
Cycloaddition Reactions: Stereochemistry
21:59
Cycloaddition Reactions: Heat or Light?
26:00
4+2 Cycloadditions
26:01
2+2 Cycloadditions
27:23
Molecular Orbital (MO) Theory of Chemical Reactions
29:26
Example 1: Molecular Orbital Theory of Bonding
29:27
Molecular Orbital (MO) Theory of Chemical Reactions
31:59
Example 2: Molecular Orbital Theory of Bonding
32:00
Molecular Orbital (MO) Theory of Chemical Reactions
33:33
MO Theory of Aromaticity, Huckel's Rule
33:34
Molecular Orbital (MO) Theory of Chemical Reactions
36:43
Review: Molecular Orbital Theory of Conjugated Systems
36:44
Molecular Orbital (MO) Theory of Chemical Reactions
44:56
Review: Molecular Orbital Theory of Conjugated Systems
44:57
Molecular Orbital (MO) Theory of Chemical Reactions
46:54
Review: Molecular Orbital Theory of Conjugated Systems
46:55
Molecular Orbital (MO) Theory of Chemical Reactions
48:36
Frontier Molecular Orbitals are Involved in Reactions
48:37
Examples
50:20
MO Theory of Pericyclic Reactions: The Woodward-Hoffmann Rules
51:51
Heat-promoted Pericyclic Reactions and Light-promoted Pericyclic Reactions
51:52
MO Theory of Pericyclic Reactions: The Woodward-Hoffmann Rules
53:42
Why is a [4+2] Cycloaddition Thermally Allowed While the [2+2] is Not?
53:43
MO Theory of Pericyclic Reactions: The Woodward-Hoffmann Rules
56:51
Why is a [2+2] Cycloaddition Photochemically Allowed?
56:52
Pericyclic Reaction Example I
59:16
Pericyclic Reaction Example I
59:17
Pericyclic Reaction Example II
1:07:40
Pericyclic Reaction Example II
1:07:41
Pericyclic Reaction Example III: Vitamin D - The Sunshine Vitamin
1:14:22
Pericyclic Reaction Example III: Vitamin D - The Sunshine Vitamin
1:14:23
Amines

34m 58s

Intro
0:00
Amines: Properties and Reactivity
0:04
Compare Amines to Alcohols
0:05
Amines: Lower Boiling Point than ROH
0:55
1) RNH₂ Has Lower Boiling Point than ROH
0:56
Amines: Better Nu: Than ROH
2:22
2) RNH₂ is a Better Nucleophile than ROH Example 1
2:23
RNH₂ is a Better Nucleophile than ROH Example 2
3:08
Amines: Better Nu: than ROH
3:47
Example
3:48
Amines are Good Bases
5:41
3) RNH₂ is a Good Base
5:42
Amines are Good Bases
7:06
Example 1
7:07
Example 2: Amino Acid
8:27
Alkyl vs. Aryl Amines
9:56
Example: Which is Strongest Base?
9:57
Alkyl vs. Aryl Amines
14:55
Verify by Comparing Conjugate Acids
14:56
Reaction of Amines
17:42
Reaction with Ketone/Aldehyde: 1° Amine (RNH₂)
17:43
Reaction of Amines
18:48
Reaction with Ketone/Aldehyde: 2° Amine (R2NH)
18:49
Use of Enamine: Synthetic Equivalent of Enolate
20:08
Use of Enamine: Synthetic Equivalent of Enolate
20:09
Reaction of Amines
24:10
Hofmann Elimination
24:11
Hofmann Elimination
26:16
Kinetic Product
26:17
Structure Analysis Using Hofmann Elimination
28:22
Structure Analysis Using Hofmann Elimination
28:23
Biological Activity of Amines
30:30
Adrenaline
31:07
Mescaline (Peyote Alkaloid)
31:22
Amino Acids, Amide, and Protein
32:14
Biological Activity of Amines
32:50
Morphine (Opium Alkaloid)
32:51
Epibatidine (Poison Dart Frog)
33:28
Nicotine
33:48
Choline (Nerve Impulse)
34:03
Section 11: Biomolecules & Polymers
Biomolecules

1h 53m 20s

Intro
0:00
Carbohydrates
1:11
D-glucose Overview
1:12
D-glucose: Cyclic Form (6-membered ring)
4:31
Cyclic Forms of Glucose: 6-membered Ring
8:24
α-D-glucopyranose & β-D-glucopyranose
8:25
Formation of a 5-Membered Ring
11:05
D-glucose: Formation of a 5-Membered Ring
11:06
Cyclic Forms of Glucose: 5-membered Ring
12:37
α-D-glucofuranose & β-D-glucofuranose
12:38
Carbohydrate Mechanism
14:03
Carbohydrate Mechanism
14:04
Reactions of Glucose: Acetal Formation
21:35
Acetal Formation: Methyl-α-D-glucoside
21:36
Hemiacetal to Acetal: Overview
24:58
Mechanism for Formation of Glycosidic Bond
25:51
Hemiacetal to Acetal: Mechanism
25:52
Formation of Disaccharides
29:34
Formation of Disaccharides
29:35
Some Polysaccharides: Starch
31:33
Amylose & Amylopectin
31:34
Starch: α-1,4-glycosidic Bonds
32:22
Properties of Starch Molecule
33:21
Some Polysaccharides: Cellulose
33:59
Cellulose: β-1,4-glycosidic bonds
34:00
Properties of Cellulose
34:59
Other Sugar-Containing Biomolecules
35:50
Ribonucleoside (RNA)
35:51
Deoxyribonucleoside (DMA)
36:59
Amino Acids & Proteins
37:32
α-amino Acids: Structure & Stereochemistry
37:33
Making a Protein (Condensation)
42:46
Making a Protein (Condensation)
42:47
Peptide Bond is Planar (Amide Resonance)
44:55
Peptide Bond is Planar (Amide Resonance)
44:56
Protein Functions
47:49
Muscle, Skin, Bones, Hair Nails
47:50
Enzymes
49:10
Antibodies
49:44
Hormones, Hemoglobin
49:58
Gene Regulation
50:20
Various Amino Acid Side Chains
50:51
Nonpolar
50:52
Polar
51:15
Acidic
51:24
Basic
51:55
Amino Acid Table
52:22
Amino Acid Table
52:23
Isoelectric Point (pI)
53:43
Isoelectric Point (pI) of Glycine
53:44
Isoelectric Point (pI) of Glycine: pH 11
56:42
Isoelectric Point (pI) of Glycine: pH 1
57:20
Isoelectric Point (pI), cont.
58:05
Asparatic Acid
58:06
Histidine
1:00:28
Isoelectric Point (pI), cont.
1:02:54
Example: What is the Net Charge of This Tetrapeptide at pH 6.0?
1:02:55
Nucleic Acids: Ribonucleosides
1:10:32
Nucleic Acids: Ribonucleosides
1:10:33
Nucleic Acids: Ribonucleotides
1:11:48
Ribonucleotides: 5' Phosphorylated Ribonucleosides
1:11:49
Ribonucleic Acid (RNA) Structure
1:12:35
Ribonucleic Acid (RNA) Structure
1:12:36
Nucleic Acids: Deoxyribonucleosides
1:14:08
Nucleic Acids: Deoxyribonucleosides
1:14:09
Deoxythymidine (T)
1:14:36
Nucleic Acids: Base-Pairing
1:15:17
Nucleic Acids: Base-Pairing
1:15:18
Double-Stranded Structure of DNA
1:18:16
Double-Stranded Structure of DNA
1:18:17
Model of DNA
1:19:40
Model of DNA
1:19:41
Space-Filling Model of DNA
1:20:46
Space-Filling Model of DNA
1:20:47
Function of RNA and DNA
1:23:06
DNA & Transcription
1:23:07
RNA & Translation
1:24:22
Genetic Code
1:25:09
Genetic Code
1:25:10
Lipids/Fats/Triglycerides
1:27:10
Structure of Glycerol
1:27:43
Saturated & Unsaturated Fatty Acids
1:27:51
Triglyceride
1:28:43
Unsaturated Fats: Lower Melting Points (Liquids/Oils)
1:29:15
Saturated Fat
1:29:16
Unsaturated Fat
1:30:10
Partial Hydrogenation
1:32:05
Saponification of Fats
1:35:11
Saponification of Fats
1:35:12
History of Soap
1:36:50
Carboxylate Salts form Micelles in Water
1:41:02
Carboxylate Salts form Micelles in Water
1:41:03
Cleaning Power of Micelles
1:42:21
Cleaning Power of Micelles
1:42:22
3-D Image of a Micelle
1:42:58
3-D Image of a Micelle
1:42:59
Synthesis of Biodiesel
1:44:04
Synthesis of Biodiesel
1:44:05
Phosphoglycerides
1:47:54
Phosphoglycerides
1:47:55
Cell Membranes Contain Lipid Bilayers
1:48:41
Cell Membranes Contain Lipid Bilayers
1:48:42
Bilayer Acts as Barrier to Movement In/Out of Cell
1:50:24
Bilayer Acts as Barrier to Movement In/Out of Cell
1:50:25
Organic Chemistry Meets Biology… Biochemistry!
1:51:12
Organic Chemistry Meets Biology… Biochemistry!
1:51:13
Polymers

45m 47s

Intro
0:00
Polymers
0:05
Monomer to Polymer: Vinyl Chloride to Polyvinyl Chloride
0:06
Polymer Properties
1:32
Polymer Properties
1:33
Natural Polymers: Rubber
2:30
Vulcanization
2:31
Natural Polymers: Polysaccharides
4:55
Example: Starch
4:56
Example: Cellulose
5:45
Natural Polymers: Proteins
6:07
Example: Keratin
6:08
DNA Strands
7:15
DNA Strands
7:16
Synthetic Polymers
8:30
Ethylene & Polyethylene: Lightweight Insulator & Airtight Plastic
8:31
Synthetic Organic Polymers
12:22
Polyethylene
12:28
Polyvinyl Chloride (PVC)
12:54
Polystyrene
13:28
Polyamide
14:34
Polymethyl Methacrylate
14:57
Kevlar
15:25
Synthetic Material Examples
16:30
How are Polymers Made?
21:00
Chain-growth Polymers Additions to Alkenes can be Radical, Cationic or Anionic
21:01
Chain Branching
22:34
Chain Branching
22:35
Special Reaction Conditions Prevent Branching
24:28
Ziegler-Natta Catalyst
24:29
Chain-Growth by Cationic Polymerization
27:35
Chain-Growth by Cationic Polymerization
27:36
Chain-Growth by Anionic Polymerization
29:35
Chain-Growth by Anionic Polymerization
29:36
Step-Growth Polymerization: Polyamides
32:16
Step-Growth Polymerization: Polyamides
32:17
Step-Growth Polymerization: Polyesters
34:23
Step-Growth Polymerization: Polyesters
34:24
Step-Growth Polymerization: Polycarbonates
35:56
Step-Growth Polymerization: Polycarbonates
35:57
Step-Growth Polymerization: Polyurethanes
37:18
Step-Growth Polymerization: Polyurethanes
37:19
Modifying Polymer Properties
39:35
Glass Transition Temperature
40:04
Crosslinking
40:42
Copolymers
40:58
Additives: Stabilizers
42:08
Additives: Flame Retardants
43:03
Additives: Plasticizers
43:41
Additives: Colorants
44:54
Section 12: Organic Synthesis
Organic Synthesis Strategies

2h 20m 24s

Intro
0:00
Organic Synthesis Strategies
0:15
Goal
0:16
Strategy
0:29
Example of a RetroSynthesis
1:30
Finding Starting Materials for Target Molecule
1:31
Synthesis Using Starting Materials
4:56
Synthesis of Alcohols by Functional Group Interconversion (FGI)
6:00
Synthesis of Alcohols by Functional Group Interconversion Overview
6:01
Alcohols by Reduction
7:43
Ketone to Alcohols
7:45
Aldehyde to Alcohols
8:26
Carboxylic Acid Derivative to Alcohols
8:36
Alcohols by Hydration of Alkenes
9:28
Hydration of Alkenes Using H₃O⁺
9:29
Oxymercuration-Demercuration
10:35
Hydroboration Oxidation
11:02
Alcohols by Substitution
11:42
Primary Alkyl Halide to Alcohols Using NaOH
11:43
Secondary Alkyl Halide to Alcohols Using Sodium Acetate
13:07
Tertiary Alkyl Halide to Alcohols Using H₂O
15:08
Synthesis of Alcohols by Forming a New C-C Bond
15:47
Recall: Alcohol & RMgBr
15:48
Retrosynthesis
17:28
Other Alcohol Disconnections
19:46
19:47
Synthesis Using PhMGgBr: Example 2
23:05
Synthesis of Alkyl Halides
26:06
Synthesis of Alkyl Halides Overview
26:07
Synthesis of Alkyl Halides by Free Radical Halogenation
27:04
Synthesis of Alkyl Halides by Free Radical Halogenation
27:05
Synthesis of Alkyl Halides by Substitution
29:06
Alcohol to Alkyl Halides Using HBr or HCl
29:07
Alcohol to Alkyl Halides Using SOCl₂
30:57
Alcohol to Alkyl Halides Using PBr₃ and Using P, I₂
31:03
Synthesis of Alkyl Halides by Addition
32:02
Alkene to Alkyl Halides Using HBr
32:03
Alkene to Alkyl Halides Using HBr & ROOR (Peroxides)
32:35
Example: Synthesis of Alkyl Halide
34:18
Example: Synthesis of Alkyl Halide
34:19
Synthesis of Ethers
39:25
Synthesis of Ethers
39:26
Example: Synthesis of an Ether
41:12
Synthesize TBME (t-butyl methyl ether) from Alcohol Starting Materials
41:13
Synthesis of Amines
46:05
Synthesis of Amines
46:06
Gabriel Synthesis of Amines
47:57
Gabriel Synthesis of Amines
47:58
Amines by SN2 with Azide Nu:
49:50
Amines by SN2 with Azide Nu:
49:51
Amines by SN2 with Cyanide Nu:
50:31
Amines by SN2 with Cyanide Nu:
50:32
Amines by Reduction of Amides
51:30
Amines by Reduction of Amides
51:31
Reductive Amination of Ketones/Aldehydes
52:42
Reductive Amination of Ketones/Aldehydes
52:43
Example : Synthesis of an Amine
53:47
Example 1: Synthesis of an Amine
53:48
Example 2: Synthesis of an Amine
56:16
Synthesis of Alkenes
58:20
Synthesis of Alkenes Overview
58:21
Synthesis of Alkenes by Elimination
59:04
Synthesis of Alkenes by Elimination Using NaOH & Heat
59:05
Synthesis of Alkenes by Elimination Using H₂SO₄ & Heat
59:57
Synthesis of Alkenes by Reduction
1:02:05
Alkyne to Cis Alkene
1:02:06
Alkyne to Trans Alkene
1:02:56
Synthesis of Alkenes by Wittig Reaction
1:03:46
Synthesis of Alkenes by Wittig Reaction
1:03:47
Retrosynthesis of an Alkene
1:05:35
Example: Synthesis of an Alkene
1:06:57
Example: Synthesis of an Alkene
1:06:58
Making a Wittig Reagent
1:10:31
Synthesis of Alkynes
1:13:09
Synthesis of Alkynes
1:13:10
Synthesis of Alkynes by Elimination (FGI)
1:13:42
First Step: Bromination of Alkene
1:13:43
Second Step: KOH Heat
1:14:22
Synthesis of Alkynes by Alkylation
1:15:02
Synthesis of Alkynes by Alkylation
1:15:03
Retrosynthesis of an Alkyne
1:16:18
Example: Synthesis of an Alkyne
1:17:40
Example: Synthesis of an Alkyne
1:17:41
Synthesis of Alkanes
1:20:52
Synthesis of Alkanes
1:20:53
Synthesis of Aldehydes & Ketones
1:21:38
Oxidation of Alcohol Using PCC or Swern
1:21:39
Oxidation of Alkene Using 1) O₃, 2)Zn
1:22:42
Reduction of Acid Chloride & Nitrile Using DiBAL-H
1:23:25
Hydration of Alkynes
1:24:55
Synthesis of Ketones by Acyl Substitution
1:26:12
Reaction with R'₂CuLi
1:26:13
Reaction with R'MgBr
1:27:13
Synthesis of Aldehydes & Ketones by α-Alkylation
1:28:00
Synthesis of Aldehydes & Ketones by α-Alkylation
1:28:01
Retrosynthesis of a Ketone
1:30:10
Acetoacetate Ester Synthesis of Ketones
1:31:05
Acetoacetate Ester Synthesis of Ketones: Step 1
1:31:06
Acetoacetate Ester Synthesis of Ketones: Step 2
1:32:13
Acetoacetate Ester Synthesis of Ketones: Step 3
1:32:50
Example: Synthesis of a Ketone
1:34:11
Example: Synthesis of a Ketone
1:34:12
Synthesis of Carboxylic Acids
1:37:15
Synthesis of Carboxylic Acids
1:37:16
Example: Synthesis of a Carboxylic Acid
1:37:59
Example: Synthesis of a Carboxylic Acid (Option 1)
1:38:00
Example: Synthesis of a Carboxylic Acid (Option 2)
1:40:51
Malonic Ester Synthesis of Carboxylic Acid
1:42:34
Malonic Ester Synthesis of Carboxylic Acid: Step 1
1:42:35
Malonic Ester Synthesis of Carboxylic Acid: Step 2
1:43:36
Malonic Ester Synthesis of Carboxylic Acid: Step 3
1:44:01
Example: Synthesis of a Carboxylic Acid
1:44:53
Example: Synthesis of a Carboxylic Acid
1:44:54
Synthesis of Carboxylic Acid Derivatives
1:48:05
Synthesis of Carboxylic Acid Derivatives
1:48:06
Alternate Ester Synthesis
1:48:58
Using Fischer Esterification
1:48:59
Using SN2 Reaction
1:50:18
Using Diazomethane
1:50:56
Using 1) LDA, 2) R'-X
1:52:15
Practice: Synthesis of an Alkyl Chloride
1:53:11
Practice: Synthesis of an Alkyl Chloride
1:53:12
Patterns of Functional Groups in Target Molecules
1:59:53
Recall: Aldol Reaction
1:59:54
β-hydroxy Ketone Target Molecule
2:01:12
α,β-unsaturated Ketone Target Molecule
2:02:20
Patterns of Functional Groups in Target Molecules
2:03:15
Recall: Michael Reaction
2:03:16
Retrosynthesis: 1,5-dicarbonyl Target Molecule
2:04:07
Patterns of Functional Groups in Target Molecules
2:06:38
Recall: Claisen Condensation
2:06:39
Retrosynthesis: β-ketoester Target Molecule
2:07:30
2-Group Target Molecule Summary
2:09:03
2-Group Target Molecule Summary
2:09:04
Example: Synthesis of Epoxy Ketone
2:11:19
Synthesize the Following Target Molecule from Cyclohexanone: Part 1 - Retrosynthesis
2:11:20
Synthesize the Following Target Molecule from Cyclohexanone: Part 2 - Synthesis
2:14:10
Example: Synthesis of a Diketone
2:16:57
Synthesis of a Diketone: Step 1 - Retrosynthesis
2:16:58
Synthesis of a Diketone: Step 2 - Synthesis
2:18:51
Section 12: Organic Synthesis & Organic Analysis
Organic Analysis: Classical & Modern Methods

46m 46s

Intro
0:00
Organic Analysis: Classical Methods
0:17
Classical Methods for Identifying Chemicals
0:18
Organic Analysis: Classical Methods
2:21
When is Structure Identification Needed?
2:22
Organic Analysis: Classical Methods
6:17
Classical Methods of Structure Identification: Physical Appearance
6:18
Classical Methods of Structure Identification: Physical Constants
6:42
Organic Analysis: Classical Methods
7:37
Classical Methods of Structure Identification: Solubility Tests - Water
7:38
Organic Analysis: Classical Methods
10:51
Classical Methods of Structure Identification: Solubility Tests - 5% aq. HCl Basic FG (Amines)
10:52
Organic Analysis: Classical Methods
11:50
Classical Methods of Structure Identification: Solubility Tests - 5% aq. NaOH Acidic FG (Carboxylic Acids, Phenols)
11:51
Organic Analysis: Classical Methods
13:28
Classical Methods of Structure Identification: Solubility Tests - 5% aq. NaHCO3 Strongly Acidic FG (Carboxylic Acids)
13:29
Organic Analysis: Classical Methods
15:35
Classical Methods of Structure Identification: Solubility Tests - Insoluble in All of the Above
15:36
Organic Analysis: Classical Methods
16:49
Classical Methods of Structure Identification: Idoform Test for Methyl Ketones
16:50
Organic Analysis: Classical Methods
22:02
Classical Methods of Structure Identification: Tollens' Test or Fehling's Solution for Aldehydes
22:03
Organic Analysis: Classical Methods
25:01
Useful Application of Classical Methods: Glucose Oxidase on Glucose Test Strips
25:02
Organic Analysis: Classical Methods
26:26
Classical Methods of Structure Identification: Starch-iodide Test
26:27
Organic Analysis: Classical Methods
28:22
Classical Methods of Structure Identification: Lucas Reagent to Determine Primary/Secondary/Tertiary Alcohol
28:23
Organic Analysis: Classical Methods
31:35
Classical Methods of Structure Identification: Silver Nitrate Test for Alkyl Halides
31:36
Organic Analysis: Classical Methods
33:23
Preparation of Derivatives
33:24
Organic Analysis: Modern Methods
36:55
Modern Methods of Chemical Characterization
36:56
Organic Analysis: Modern Methods
40:36
Checklist for Manuscripts Submitted to the ACS Journal Organic Letters
40:37
Organic Analysis: Modern Methods
42:39
Checklist for Manuscripts Submitted to the ACS Journal Organic Letters
42:40
Analysis of Stereochemistry

1h 2m 52s

Intro
0:00
Chirality & Optical Activity
0:32
Levorotatory & Dextrorotatory
0:33
Example: Optically Active?
2:22
Example: Optically Active?
2:23
Measurement of Specific Rotation, [α]
5:09
Measurement of Specific Rotation, [α]
5:10
Example: Calculation of Specific Rotation
8:56
Example: Calculation of Specific Rotation
8:57
Variability of Specific Rotation, [α]
12:52
Variability of Specific Rotation, [α]
12:53
Other Measures of Optical Activity: ORD and CD
15:04
Optical Rotary Dispersion (ORD)
15:05
Circular Dischroism (CD)
18:32
Circular Dischroism (CD)
18:33
Mixtures of Enantiomers
20:16
Racemic Mixtures
20:17
Unequal Mixtures of Enantiomers
21:36
100% ee
22:48
0% ee
23:34
Example: Definition of ee?
24:00
Example: Definition of ee?
24:01
Analysis of Optical Purity: [α]
27:47
[α] Measurement Can Be Used for Known Compounds
27:48
Analysis of Optical Purity: [α]
34:30
NMR Methods Using a Chiral Derivatizing Agent (CDA): Mosher's Reagent
34:31
Analysis of Optical Purity: [α]
40:01
NMR Methods Using a Chiral Derivatizing Agent (CDA): CDA Salt Formation
40:02
Analysis of Optical Purity: Chromatography
42:46
Chiral Chromatography
42:47
Stereochemistry Analysis by NMR: J Values (Coupling Constant)
51:28
NMR Methods for Structure Determination
51:29
Stereochemistry Analysis by NRM: NOE
57:00
NOE - Nuclear Overhauser Effect ( 2D Versions: NOESY or ROESY)
57:01
Section 13: Spectroscopy
Infrared Spectroscopy, Part I

1h 4m

Intro
0:00
Infrared (IR) Spectroscopy
0:09
Introduction to Infrared (IR) Spectroscopy
0:10
Intensity of Absorption Is Proportional to Change in Dipole
3:08
IR Spectrum of an Alkane
6:08
Pentane
6:09
IR Spectrum of an Alkene
13:12
1-Pentene
13:13
IR Spectrum of an Alkyne
15:49
1-Pentyne
15:50
IR Spectrum of an Aromatic Compound
18:02
Methylbenzene
18:24
IR of Substituted Aromatic Compounds
24:04
IR of Substituted Aromatic Compounds
24:05
IR Spectrum of 1,2-Disubstituted Aromatic
25:30
1,2-dimethylbenzene
25:31
IR Spectrum of 1,3-Disubstituted Aromatic
27:15
1,3-dimethylbenzene
27:16
IR Spectrum of 1,4-Disubstituted Aromatic
28:41
1,4-dimethylbenzene
28:42
IR Spectrum of an Alcohol
29:34
1-pentanol
29:35
IR Spectrum of an Amine
32:39
1-butanamine
32:40
IR Spectrum of a 2° Amine
34:50
Diethylamine
34:51
IR Spectrum of a 3° Amine
35:47
Triethylamine
35:48
IR Spectrum of a Ketone
36:41
2-butanone
36:42
IR Spectrum of an Aldehyde
40:10
Pentanal
40:11
IR Spectrum of an Ester
42:38
Butyl Propanoate
42:39
IR Spectrum of a Carboxylic Acid
44:26
Butanoic Acid
44:27
Sample IR Correlation Chart
47:36
Sample IR Correlation Chart: Wavenumber and Functional Group
47:37
Predicting IR Spectra: Sample Structures
52:06
Example 1
52:07
Example 2
53:29
Example 3
54:40
Example 4
57:08
Example 5
58:31
Example 6
59:07
Example 7
1:00:52
Example 8
1:02:20
Infrared Spectroscopy, Part II

48m 34s

Intro
0:00
Interpretation of IR Spectra: a Basic Approach
0:05
Interpretation of IR Spectra: a Basic Approach
0:06
Other Peaks to Look for
3:39
Examples
5:17
Example 1
5:18
Example 2
9:09
Example 3
11:52
Example 4
14:03
Example 5
16:31
Example 6
19:31
Example 7
22:32
Example 8
24:39
IR Problems Part 1
28:11
IR Problem 1
28:12
IR Problem 2
31:14
IR Problem 3
32:59
IR Problem 4
34:23
IR Problem 5
35:49
IR Problem 6
38:20
IR Problems Part 2
42:36
IR Problem 7
42:37
IR Problem 8
44:02
IR Problem 9
45:07
IR Problems10
46:10
Nuclear Magnetic Resonance (NMR) Spectroscopy, Part I

1h 32m 14s

Intro
0:00
Purpose of NMR
0:14
Purpose of NMR
0:15
How NMR Works
2:17
How NMR Works
2:18
Information Obtained From a ¹H NMR Spectrum
5:51
No. of Signals, Integration, Chemical Shifts, and Splitting Patterns
5:52
Number of Signals in NMR (Chemical Equivalence)
7:52
Example 1: How Many Signals in ¹H NMR?
7:53
Example 2: How Many Signals in ¹H NMR?
9:36
Example 3: How Many Signals in ¹H NMR?
12:15
Example 4: How Many Signals in ¹H NMR?
13:47
Example 5: How Many Signals in ¹H NMR?
16:12
Size of Signals in NMR (Peak Area or Integration)
21:23
Size of Signals in NMR (Peak Area or Integration)
21:24
Using Integral Trails
25:15
Example 1: C₈H₁₈O
25:16
Example 2: C₃H₈O
27:17
Example 3: C₇H₈
28:21
Location of NMR Signal (Chemical Shift)
29:05
Location of NMR Signal (Chemical Shift)
29:06
¹H NMR Chemical Shifts
33:20
¹H NMR Chemical Shifts
33:21
¹H NMR Chemical Shifts (Protons on Carbon)
37:03
¹H NMR Chemical Shifts (Protons on Carbon)
37:04
Chemical Shifts of H's on N or O
39:01
Chemical Shifts of H's on N or O
39:02
Estimating Chemical Shifts
41:13
Example 1: Estimating Chemical Shifts
41:14
Example 2: Estimating Chemical Shifts
43:22
Functional Group Effects are Additive
45:28
Calculating Chemical Shifts
47:38
Methylene Calculation
47:39
Methine Calculation
48:20
Protons on sp³ Carbons: Chemical Shift Calculation Table
48:50
Example: Estimate the Chemical Shift of the Selected H
50:29
Effects of Resonance on Chemical Shifts
53:11
Example 1: Effects of Resonance on Chemical Shifts
53:12
Example 2: Effects of Resonance on Chemical Shifts
55:09
Example 3: Effects of Resonance on Chemical Shifts
57:08
Shape of NMR Signal (Splitting Patterns)
59:17
Shape of NMR Signal (Splitting Patterns)
59:18
Understanding Splitting Patterns: The 'n+1 Rule'
1:01:24
Understanding Splitting Patterns: The 'n+1 Rule'
1:01:25
Explanation of n+1 Rule
1:02:42
Explanation of n+1 Rule: One Neighbor
1:02:43
Explanation of n+1 Rule: Two Neighbors
1:06:23
Summary of Splitting Patterns
1:06:24
Summary of Splitting Patterns
1:10:45
Predicting ¹H NMR Spectra
1:10:46
Example 1: Predicting ¹H NMR Spectra
1:13:30
Example 2: Predicting ¹H NMR Spectra
1:19:07
Example 3: Predicting ¹H NMR Spectra
1:23:50
Example 4: Predicting ¹H NMR Spectra
1:29:27
Nuclear Magnetic Resonance (NMR) Spectroscopy, Part II

2h 3m 48s

Intro
0:00
¹H NMR Problem-Solving Strategies
0:18
Step 1: Analyze IR Spectrum (If Provided)
0:19
Step 2: Analyze Molecular Formula (If Provided)
2:06
Step 3: Draw Pieces of Molecule
3:49
Step 4: Confirm Pieces
6:30
Step 5: Put the Pieces Together!
7:23
Step 6: Check Your Answer!
8:21
Examples
9:17
Example 1: Determine the Structure of a C₉H₁₀O₂ Compound with the Following ¹H NMR Data
9:18
Example 2: Determine the Structure of a C₉H₁₀O₂ Compound with the Following ¹H NMR Data
17:27
¹H NMR Practice
20:57
¹H NMR Practice 1: C₁₀H₁₄
20:58
¹H NMR Practice 2: C₄H₈O₂
29:50
¹H NMR Practice 3: C₆H₁₂O₃
39:19
¹H NMR Practice 4: C₈H₁₈
50:19
More About Coupling Constants (J Values)
57:11
Vicinal (3-bond) and Geminal (2-bond)
57:12
Cyclohexane (ax-ax) and Cyclohexane (ax-eq) or (eq-eq)
59:50
Geminal (Alkene), Cis (Alkene), and Trans (Alkene)
1:02:40
Allylic (4-bond) and W-coupling (4-bond) (Rigid Structures Only)
1:04:05
¹H NMR Advanced Splitting Patterns
1:05:39
Example 1: ¹H NMR Advanced Splitting Patterns
1:05:40
Example 2: ¹H NMR Advanced Splitting Patterns
1:10:01
Example 3: ¹H NMR Advanced Splitting Patterns
1:13:45
¹H NMR Practice
1:22:53
¹H NMR Practice 5: C₁₁H₁₇N
1:22:54
¹H NMR Practice 6: C₉H₁₀O
1:34:04
¹³C NMR Spectroscopy
1:44:49
¹³C NMR Spectroscopy
1:44:50
¹³C NMR Chemical Shifts
1:47:24
¹³C NMR Chemical Shifts Part 1
1:47:25
¹³C NMR Chemical Shifts Part 2
1:48:59
¹³C NMR Practice
1:50:16
¹³C NMR Practice 1
1:50:17
¹³C NMR Practice 2
1:58:30
C-13 DEPT NMR Experiments

23m 10s

Intro
0:00
C-13 DEPT NMR Spectoscopy
0:13
Overview
0:14
C-13 DEPT NMR Spectoscopy, Cont.
3:31
Match C-13 Peaks to Carbons on Structure
3:32
C-13 DEPT NMR Spectoscopy, Cont.
8:46
Predict the DEPT-90 and DEPT-135 Spectra for the Given Compound
8:47
C-13 DEPT NMR Spectoscopy, Cont.
12:30
Predict the DEPT-90 and DEPT-135 Spectra for the Given Compound
12:31
C-13 DEPT NMR Spectoscopy, Cont.
17:19
Determine the Structure of an Unknown Compound using IR Spectrum and C-13 DEPT NMR
17:20
Two-Dimensional NMR Techniques: COSY

33m 39s

Intro
0:00
Two-Dimensional NMR Techniques: COSY
0:14
How Do We Determine Which Protons are Related in the NMR?
0:15
Two-Dimensional NMR Techniques: COSY
1:48
COSY Spectra
1:49
Two-Dimensional NMR Techniques: COSY
7:00
COSY Correlation
7:01
Two-Dimensional NMR Techniques: COSY
8:55
Complete the COSY NMR Spectrum for the Given Compoun
8:56
NMR Practice Problem
15:40
Provide a Structure for the Unknown Compound with the H NMR and COSY Spectra Shown
15:41
Two-Dimensional NMR Techniques: HETCOR & HMBC

15m 5s

Intro
0:00
HETCOR
0:15
Heteronuclear Correlation Spectroscopy
0:16
HETCOR
2:04
HETCOR Example
2:05
HMBC
11:07
Heteronuclear Multiple Bond Correlation
11:08
HMBC
13:14
HMB Example
13:15
Mass Spectrometry

1h 28m 35s

Intro
0:00
Introduction to Mass Spectrometry
0:37
Uses of Mass Spectrometry: Molecular Mass
0:38
Uses of Mass Spectrometry: Molecular Formula
1:04
Uses of Mass Spectrometry: Structural Information
1:21
Uses of Mass Spectrometry: In Conjunction with Gas Chromatography
2:03
Obtaining a Mass Spectrum
2:59
Obtaining a Mass Spectrum
3:00
The Components of a Mass Spectrum
6:44
The Components of a Mass Spectrum
6:45
What is the Mass of a Single Molecule
12:13
Example: CH₄
12:14
Example: ¹³CH₄
12:51
What Ratio is Expected for the Molecular Ion Peaks of C₂H₆?
14:20
Other Isotopes of High Abundance
16:30
Example: Cl Atoms
16:31
Example: Br Atoms
18:33
Mass Spectrometry of Chloroethane
19:22
Mass Spectrometry of Bromobutane
21:23
Isotopic Abundance can be Calculated
22:48
What Ratios are Expected for the Molecular Ion Peaks of CH₂Br₂?
22:49
Determining Molecular Formula from High-resolution Mass Spectrometry
26:53
Exact Masses of Various Elements
26:54
Fragmentation of various Functional Groups
28:42
What is More Stable, a Carbocation C⁺ or a Radical R?
28:43
Fragmentation is More Likely If It Gives Relatively Stable Carbocations and Radicals
31:37
Mass Spectra of Alkanes
33:15
Example: Hexane
33:16
Fragmentation Method 1
34:19
Fragmentation Method 2
35:46
Fragmentation Method 3
36:15
Mass of Common Fragments
37:07
Mass of Common Fragments
37:08
Mass Spectra of Alkanes
39:28
Mass Spectra of Alkanes
39:29
What are the Peaks at m/z 15 and 71 So Small?
41:01
Branched Alkanes
43:12
Explain Why the Base Peak of 2-methylhexane is at m/z 43 (M-57)
43:13
Mass Spectra of Alkenes
45:42
Mass Spectra of Alkenes: Remove 1 e⁻
45:43
Mass Spectra of Alkenes: Fragment
46:14
High-Energy Pi Electron is Most Likely Removed
47:59
Mass Spectra of Aromatic Compounds
49:01
Mass Spectra of Aromatic Compounds
49:02
Mass Spectra of Alcohols
51:32
Mass Spectra of Alcohols
51:33
Mass Spectra of Ethers
54:53
Mass Spectra of Ethers
54:54
Mass Spectra of Amines
56:49
Mass Spectra of Amines
56:50
Mass Spectra of Aldehydes & Ketones
59:23
Mass Spectra of Aldehydes & Ketones
59:24
McLafferty Rearrangement
1:01:29
McLafferty Rearrangement
1:01:30
Mass Spectra of Esters
1:04:15
Mass Spectra of Esters
1:01:16
Mass Spectrometry Discussion I
1:05:01
For the Given Molecule (M=58), Do You Expect the More Abundant Peak to Be m/z 15 or m/z 43?
1:05:02
Mass Spectrometry Discussion II
1:08:13
For the Given Molecule (M=74), Do You Expect the More Abundant Peak to Be m/z 31, m/z 45, or m/z 59?
1:08:14
Mass Spectrometry Discussion III
1:11:42
Explain Why the Mass Spectra of Methyl Ketones Typically have a Peak at m/z 43
1:11:43
Mass Spectrometry Discussion IV
1:14:46
In the Mass Spectrum of the Given Molecule (M=88), Account for the Peaks at m/z 45 and m/z 57
1:14:47
Mass Spectrometry Discussion V
1:18:25
How Could You Use Mass Spectrometry to Distinguish Between the Following Two Compounds (M=73)?
1:18:26
Mass Spectrometry Discussion VI
1:22:45
What Would be the m/z Ratio for the Fragment for the Fragment Resulting from a McLafferty Rearrangement for the Following Molecule (M=114)?
1:22:46
Section 14: Organic Chemistry Lab
Completing the Reagent Table for Prelab

21m 9s

Intro
0:00
Sample Reagent Table
0:11
Reagent Table Overview
0:12
Calculate Moles of 2-bromoaniline
6:44
Calculate Molar Amounts of Each Reagent
9:20
Calculate Mole of NaNO₂
9:21
Calculate Moles of KI
10:33
Identify the Limiting Reagent
11:17
Which Reagent is the Limiting Reagent?
11:18
Calculate Molar Equivalents
13:37
Molar Equivalents
13:38
Calculate Theoretical Yield
16:40
Theoretical Yield
16:41
Calculate Actual Yield (%Yield)
18:30
Actual Yield (%Yield)
18:31
Introduction to Melting Points

16m 10s

Intro
0:00
Definition of a Melting Point (mp)
0:04
Definition of a Melting Point (mp)
0:05
Solid Samples Melt Gradually
1:49
Recording Range of Melting Temperature
2:04
Melting Point Theory
3:14
Melting Point Theory
3:15
Effects of Impurities on a Melting Point
3:57
Effects of Impurities on a Melting Point
3:58
Special Exception: Eutectic Mixtures
5:09
Freezing Point Depression by Solutes
5:39
Melting Point Uses
6:19
Solid Compound
6:20
Determine Purity of a Sample
6:42
Identify an Unknown Solid
7:06
Recording a Melting Point
9:03
Pack 1-3 mm of Dry Powder in MP Tube
9:04
Slowly Heat Sample
9:55
Record Temperature at First Sign of Melting
10:33
Record Temperature When Last Crystal Disappears
11:26
Discard MP Tube in Glass Waste
11:32
Determine Approximate MP
11:42
Tips, Tricks and Warnings
12:28
Use Small, Tightly Packed Sample
12:29
Be Sure MP Apparatus is Cool
12:45
Never Reuse a MP Tube
13:16
Sample May Decompose
13:30
If Pure Melting Point (MP) Doesn't Match Literature
14:20
Melting Point Lab

8m 17s

Intro
0:00
Melting Point Tubes
0:40
Melting Point Apparatus
3:42
Recording a melting Point
5:50
Introduction to Recrystallization

22m

Intro
0:00
Crystallization to Purify a Solid
0:10
Crude Solid
0:11
Hot Solution
0:20
Crystals
1:09
Supernatant Liquid
1:20
Theory of Crystallization
2:34
Theory of Crystallization
2:35
Analysis and Obtaining a Second Crop
3:40
Crystals → Melting Point, TLC
3:41
Supernatant Liquid → Crude Solid → Pure Solid
4:18
Crystallize Again → Pure Solid (2nd Crop)
4:32
Choosing a Solvent
5:19
1. Product is Very Soluble at High Temperatures
5:20
2. Product has Low Solubility at Low Temperatures
6:00
3. Impurities are Soluble at All Temperatures
6:16
Check Handbooks for Suitable Solvents
7:33
Why Isn't This Dissolving?!
8:46
If Solid Remains When Solution is Hot
8:47
Still Not Dissolved in Hot Solvent?
10:18
Where Are My Crystals?!
12:23
If No Crystals Form When Solution is Cooled
12:24
Still No Crystals?
14:59
Tips, Tricks and Warnings
16:26
Always Use a Boiling Chip or Stick!
16:27
Use Charcoal to Remove Colored Impurities
16:52
Solvent Pairs May Be Used
18:23
Product May 'Oil Out'
20:11
Recrystallization Lab

19m 7s

Intro
0:00
Step 1: Dissolving the Solute in the Solvent
0:12
Hot Filtration
6:33
Step 2: Cooling the Solution
8:01
Step 3: Filtering the Crystals
12:08
Step 4: Removing & Drying the Crystals
16:10
Introduction to Distillation

25m 54s

Intro
0:00
Distillation: Purify a Liquid
0:04
Simple Distillation
0:05
Fractional Distillation
0:55
Theory of Distillation
1:04
Theory of Distillation
1:05
Vapor Pressure and Volatility
1:52
Vapor Pressure
1:53
Volatile Liquid
2:28
Less Volatile Liquid
3:09
Vapor Pressure vs. Boiling Point
4:03
Vapor Pressure vs. Boiling Point
4:04
Increasing Vapor Pressure
4:38
The Purpose of Boiling Chips
6:46
The Purpose of Boiling Chips
6:47
Homogeneous Mixtures of Liquids
9:24
Dalton's Law
9:25
Raoult's Law
10:27
Distilling a Mixture of Two Liquids
11:41
Distilling a Mixture of Two Liquids
11:42
Simple Distillation: Changing Vapor Composition
12:06
Vapor & Liquid
12:07
Simple Distillation: Changing Vapor Composition
14:47
Azeotrope
18:41
Fractional Distillation: Constant Vapor Composition
19:42
Fractional Distillation: Constant Vapor Composition
19:43
Distillation Lab

24m 13s

Intro
0:00
Glassware Overview
0:04
Heating a Sample
3:09
Bunsen Burner
3:10
Heating Mantle 1
4:45
Heating Mantle 2
6:18
Hot Plate
7:10
Simple Distillation Lab
8:37
Fractional Distillation Lab
17:13
Removing the Distillation Set-Up
22:41
Introduction to TLC (Thin-Layer Chromatography)

28m 51s

Intro
0:00
Chromatography
0:06
Purification & Analysis
0:07
Types of Chromatography: Thin-layer, Column, Gas, & High Performance Liquid
0:24
Theory of Chromatography
0:44
Theory of Chromatography
0:45
Performing a Thin-layer Chromatography (TLC) Analysis
2:30
Overview: Thin-layer Chromatography (TLC) Analysis
2:31
Step 1: 'Spot' the TLC Plate
4:11
Step 2: Prepare the Developing Chamber
5:54
Step 3: Develop the TLC Plate
7:30
Step 4: Visualize the Spots
9:02
Step 5: Calculate the Rf for Each Spot
12:00
Compound Polarity: Effect on Rf
16:50
Compound Polarity: Effect on Rf
16:51
Solvent Polarity: Effect on Rf
18:47
Solvent Polarity: Effect on Rf
18:48
Example: EtOAc & Hexane
19:35
Other Types of Chromatography
22:27
Thin-layer Chromatography (TLC)
22:28
Column Chromatography
22:56
High Performance Liquid (HPLC)
23:59
Gas Chromatography (GC)
24:38
Preparative 'prep' Scale Possible
28:05
TLC Analysis Lab

20m 50s

Intro
0:00
Step 1: 'Spot' the TLC Plate
0:06
Step 2: Prepare the Developing Chamber
4:06
Step 3: Develop the TLC Plate
6:26
Step 4: Visualize the Spots
7:45
Step 5: Calculate the Rf for Each Spot
11:48
How to Make Spotters
12:58
TLC Plate
16:04
Flash Column Chromatography
17:11
Introduction to Extractions

34m 25s

Intro
0:00
Extraction Purify, Separate Mixtures
0:07
Adding a Second Solvent
0:28
Mixing Two Layers
0:38
Layers Settle
0:54
Separate Layers
1:05
Extraction Uses
1:20
To Separate Based on Difference in Solubility/Polarity
1:21
To Separate Based on Differences in Reactivity
2:11
Separate & Isolate
2:20
Theory of Extraction
3:03
Aqueous & Organic Phases
3:04
Solubility: 'Like Dissolves Like'
3:25
Separation of Layers
4:06
Partitioning
4:14
Distribution Coefficient, K
5:03
Solutes Partition Between Phases
5:04
Distribution Coefficient, K at Equilibrium
6:27
Acid-Base Extractions
8:09
Organic Layer
8:10
Adding Aqueous HCl & Mixing Two Layers
8:46
Neutralize (Adding Aqueous NaOH)
10:05
Adding Organic Solvent Mix Two Layers 'Back Extract'
10:24
Final Results
10:43
Planning an Acid-Base Extraction, Part 1
11:01
Solute Type: Neutral
11:02
Aqueous Solution: Water
13:40
Solute Type: Basic
14:43
Solute Type: Weakly Acidic
15:23
Solute Type: Acidic
16:12
Planning an Acid-Base Extraction, Part 2
17:34
Planning an Acid-Base Extraction
17:35
Performing an Extraction
19:34
Pour Solution into Sep Funnel
19:35
Add Second Liquid
20:07
Add Stopper, Cover with Hand, Remove from Ring
20:48
Tip Upside Down, Open Stopcock to Vent Pressure
21:00
Shake to Mix Two Layers
21:30
Remove Stopper & Drain Bottom Layer
21:40
Reaction Work-up: Purify, Isolate Product
22:03
Typical Reaction is Run in Organic Solvent
22:04
Starting a Reaction Work-up
22:33
Extracting the Product with Organic Solvent
23:17
Combined Extracts are Washed
23:40
Organic Layer is 'Dried'
24:23
Finding the Product
26:38
Which Layer is Which?
26:39
Where is My Product?
28:00
Tips, Tricks and Warnings
29:29
Leaking Sep Funnel
29:30
Caution When Mixing Layers & Using Ether
30:17
If an Emulsion Forms
31:51
Extraction Lab

14m 49s

Intro
0:00
Step 1: Preparing the Separatory Funnel
0:03
Step 2: Adding Sample
1:18
Step 3: Mixing the Two Layers
2:59
Step 4: Draining the Bottom Layers
4:59
Step 5: Performing a Second Extraction
5:50
Step 6: Drying the Organic Layer
7:21
Step 7: Gravity Filtration
9:35
Possible Extraction Challenges
12:55
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Lecture Comments (109)

2 answers

Last reply by: Professor Starkey
Tue Jul 13, 2021 6:04 PM

Post by Michael De La Rosa on July 13, 2021

Great video. I have used what I learned about Alkene nomenclature on practice questions and have gotten most of them right. Although there is one that I can not answer correctly.

What is the IUPAC name of a cyclooctadiene with double bonds at carbons 1 and 6 and a propene group at its carbon 3. The propene group has its double bond at the end of it.

I wanted to paste a picture of the molecule, but this comment box will not let me.

Here is the link to the site which has the molecule. It is Part C question 5.

2 answers

Last reply by: Professor Starkey
Sun Oct 4, 2020 7:12 PM

Post by John Gibson on October 4, 2020

Dr. Starkey,

@29:00 when naming the molecule do we have to denote whether it is "cis" or "trans"?
I was wondering if the correct name would be, "trans-7-phenyl-2-heptene-6-yne" or "trans-7-phenylhept-2-en-6-yne"?

Thank you.

2 answers

Last reply by: Professor Starkey
Thu Oct 24, 2019 9:33 PM

Post by Euichul Jung on October 20, 2019

Hi Dr. Starkey,

I have a question!!!!

At 9:50,  I thought that IUPAC name of the molecule is 3-ethyl-2-methyl-1-pentene because I just ranked the carbon which is the closest to the pi bond. so why is not 3-ethyl-2-methyl-1-pentene??

1 answer

Last reply by: Professor Starkey
Tue May 15, 2018 1:08 PM

Post by Parsa Abadi on May 14, 2018

at 11:30 how do you know which chain two number, the first chain has 1 pi bond and the other has 3 pi bonds?

1 answer

Last reply by: Professor Starkey
Tue May 15, 2018 1:06 PM

Post by Parsa Abadi on May 14, 2018

At 6:03 why is it dimethylethyl and not just methylethyl? why is there a prefix di-? also why is it dimethylethyl and not diethylmethyl?
Thank You

1 answer

Last reply by: Professor Starkey
Fri Feb 3, 2017 9:55 PM

Post by DOMNIC KIPLANGAT on December 24, 2016

I think the 3-propyl-1-octene in the alkenes section should have been 2-propyl-1-octene?

1 answer

Last reply by: Professor Starkey
Sun May 15, 2016 12:22 PM

Post by dayun hwang on May 13, 2016

Hi Dr. Starkey, In the cycloalkane nomenclature, there was a 1-fluro 1-methyl-3-(1-methyl propyl) cyclohexane example, I was wondering that why it can't be (numbering) 1-(1-methyl propyl) 3-fluoro 3-methyl. I studied organic chemistry for the first time with your lectures, and it is amazing! I am really appreciate for your lectures, thank you!

2 answers

Last reply by: Professor Starkey
Tue Jan 19, 2016 1:14 PM

Post by Alexandra Baran on January 19, 2016

Professor Starkey,

At 70:45 in the lecture.  You discuss naming the meta-bromoidobenzene.  Is the idobenzene the parent because of alphabetical order?

1 answer

Last reply by: Professor Starkey
Thu Apr 30, 2015 12:55 AM

Post by Rene Whitaker on April 29, 2015

At 63:04, it is not necessary to specify "1-one" since it is assumed the carbonyl is at carbon 1 in a cyclic compound, correct?

1 answer

Last reply by: Professor Starkey
Mon Apr 27, 2015 7:16 PM

Post by Lyngage Tan on April 26, 2015

hi dr. starkey on minute 27 the name should be 3-methyl-4-phenyl-1-pentyne instead of 4-methyl-5-phenyl-1-hexyne. am i right on this one?

1 answer

Last reply by: Professor Starkey
Fri Nov 7, 2014 12:50 AM

Post by Cassia Tremblay on November 6, 2014

Are there no practice questions for nomenclature? Or is my computer just being funky?

1 answer

Last reply by: Professor Starkey
Sun Nov 2, 2014 1:46 PM

Post by Fobe Aloo on November 2, 2014

On minute 28, shouldn't the structure be pentyne?  The parent chain only has 5 carbons.

1 answer

Last reply by: Professor Starkey
Sun Oct 12, 2014 11:59 PM

Post by Brijae Chavarria on October 12, 2014

Shouldn't the 3-propyl-1-octene in the alkenes section be named 2-propyl-1-octene?

2 answers

Last reply by: Professor Starkey
Wed Oct 8, 2014 10:54 AM

Post by BENSON SAMKUTTY on October 8, 2014

Hi Dr. Starkey, In the amine section of the lecture, there was a t-butylamine example, I was wondering is it really 2-methylpropanamine, because the amino group is on carbon 2, and it is not properly identified or designated. Could it be N,N-dimethylethanamide? Please let me know when you get a chance. Great lectures by the way, I'm learning a lot!

1 answer

Last reply by: Professor Starkey
Sun Jun 1, 2014 6:04 PM

Post by Julie Mohamed on May 31, 2014

Alcohol nomenclature:

There is two OH groups on example #3. Why do you not include the OH that is on carbon #1 in the name? would it be 1,4- pentanediol?

1 answer

Last reply by: Professor Starkey
Sat May 10, 2014 12:09 AM

Post by somia abdelgawad on May 7, 2014

ON 26 MINTUE TEH THIRD MOLECULE SHOULD BE PENTYNE NOT HEXYNE I THINK. PLEASE LET ME KNOW.

1 answer

Last reply by: Professor Starkey
Sat May 10, 2014 12:06 AM

Post by somia abdelgawad on May 7, 2014

I FEEL BAD I DID NOT PURCHASE EDUCATOR.COM IN THE BEGINING OF THE SEMESTER BUT I THINK YOU ARE SUCH A GREAT WONDERFUL HELP. THANK YOU SO MUCH.

1 answer

Last reply by: Professor Starkey
Sat May 10, 2014 12:11 AM

Post by somia abdelgawad on May 7, 2014

on 11 mintue the foruth compound should be 2-propyl-1-octene not 3-propyle-1-octene. I AM RIGHT OR NOT.

1 answer

Last reply by: Professor Starkey
Sun Feb 16, 2014 11:23 PM

Post by nneka igwemadu on February 14, 2014

Can someone direct me to where she talks about (Haloalkanes) I'm using that term in search and not finding anything.
Thank you

1 answer

Last reply by: Professor Starkey
Sun Feb 9, 2014 2:44 PM

Post by Angela Gomez on February 7, 2014

in the ester nomenclature, why you did not use the cis or trans when you named the phenylmethyl 4-pentenoate

1 answer

Last reply by: Professor Starkey
Wed Nov 13, 2013 1:35 AM

Post by Johnathan Beldin on November 12, 2013

For 2-cyclohexen-1-one could it just be named 2-cyclohexenone since the location of the carbonyl group has to be carbon number 1?

1 answer

Last reply by: Professor Starkey
Fri Oct 18, 2013 2:06 PM

Post by Nicholas Elias on October 16, 2013

If you have a cycloalkane ring connected to a longer alkyl chain would the chain be the parent constituent since it is longer or would the cyclo hexane group?? Ex a cyclohexane connected to an n-octyl group

1 answer

Last reply by: Professor Starkey
Tue Oct 8, 2013 11:44 PM

Post by Ardeshir Badr on October 8, 2013

at around 10:53 is it not 2 propyl octene? not 3 propyl octene, you even said at carbon 2 its propyl but then wrote 3 propyl 1 octene, am i missing something?

1 answer

Last reply by: Professor Starkey
Thu Oct 3, 2013 11:35 PM

Post by Eric Garnett on October 2, 2013

Would a FG of NO2 still be an amine group?
e.g.
2,4-Dinitrophenol

2 answers

Last reply by: Professor Starkey
Tue Sep 17, 2013 10:21 PM

Post by daniel nicoll on September 17, 2013

In the last example for the alkynes (hept-2-en-6-yne), would you include a trans- for the double bond in the name?

3 answers

Last reply by: Professor Starkey
Sun Aug 11, 2013 10:48 AM

Post by Scott Katzelnick on August 8, 2013

At 23:15 you named an alkene (E)-2,3,4-Trimethyl-3-hexene. Wouldn't the correct mane be (Z)-2-Ethyl-3,4-dimethyl-2-pentene as this would give the double bond the lower number with the same number of constituents with the same numbering as your name?

1 answer

Last reply by: Professor Starkey
Wed Jul 10, 2013 2:16 AM

Post by Jon Sorensen on July 9, 2013

so at 29:20 is trans also included?

1 answer

Last reply by: Professor Starkey
Wed May 15, 2013 11:33 PM

Post by mateusz marciniak on May 15, 2013

hi professor i have a general question, whenever your naming compounds like ketones do you have to write out the 1 along with the name of the carbon chain or can you write out the parent name and put any functional groups like usual

1 answer

Last reply by: Professor Starkey
Tue Apr 30, 2013 10:37 PM

Post by Nawaphan Jedjomnongkit on April 30, 2013

In Aromatic nomenclature slide, when give number to C for naphthalene , why skip the C in the middle? Thank you

1 answer

Last reply by: Professor Starkey
Tue Apr 30, 2013 11:36 PM

Post by Nawaphan Jedjomnongkit on April 29, 2013

In cycloalkane nomenclature we have to give number depend on alphabet of the substituent, so from your last example if you didn't change the methyl to ethyl, which C will be the first one because now both substituents begin with the same alphabet? Thank you!

1 answer

Last reply by: Professor Starkey
Sun Feb 17, 2013 5:28 PM

Post by Ashley Nicole Leung on February 16, 2013

how do you determine if a structure is ortho, meta, or para when the group is only on one substituent?

1 answer

Last reply by: Professor Starkey
Tue Jan 29, 2013 8:53 AM

Post by Norma Saderi Moreira on January 29, 2013

Hello Dr: Laurie ,

Would you have any recommendations of good books with good exercises to practice the nomenclature and stereochemistry ?

1 answer

Last reply by: Professor Starkey
Thu Jan 3, 2013 11:28 PM

Post by Aaron Harper on January 3, 2013

There appears to be a mistake; at about 10:57, the compound is 2-propyl-1-octene, not 3-propyl-1-octene.

1 answer

Last reply by: Professor Starkey
Thu Nov 29, 2012 10:21 PM

Post by kathy jarman on November 29, 2012

At 6:06, I thought that the prefixes such as "di" is included in the alphabetization when the substituent name is in parentheses (part of the branch name). If so, would the name 2-(1,1-dimethylethyl)-1-ethylcyclobutane instead of 1-ethyl-2-(1,1-dimethylethyl)cyclobutane?

1 answer

Last reply by: Professor Starkey
Fri Oct 19, 2012 10:57 AM

Post by Dennis Antigha on October 18, 2012

When a cycloalkane is not the parent chain, do you name it as cycloalkyl or cycloalkane. example 2-cyclopentyl-1-butene or 2-cyclopentane-1-butene

1 answer

Last reply by: Professor Starkey
Fri Oct 12, 2012 8:29 PM

Post by Dennis Antigha on October 11, 2012

For frame 46:22 why not call out the position of the amonio group say something like 2-Ethylpropan-2-amine?

Thank you

2 answers

Last reply by: Professor Starkey
Sun Oct 7, 2012 11:40 AM

Post by Alan Delez on October 5, 2012

Hello Dr. Starkey and all students,
For the 2nd compound discussed in min 4:30. Could that also be written as 1-fluoro-1-chloro-3-iso-butylcyclohexane?

1 answer

Last reply by: Professor Starkey
Fri Sep 28, 2012 10:43 AM

Post by Saith Sanchez on September 26, 2012

why can't we use the term T-butyl on example 3 of the cycloalkane nomenclature?

1 answer

Last reply by: Professor Starkey
Thu Jul 19, 2012 12:46 AM

Post by Bien Grama on July 17, 2012

i supposed to finished this topic for less than 2 hours.,., but it took me almost one day .,., i keep on reloading! and reloading!and reloading ! wow this is not what i payed for

0 answers

Post by harman bhullar on June 16, 2012

i just saw your reply professor but i let the entire thing load and tried multiple browsers. i cant skip ahead past ether section.

2 answers

Last reply by: Jessica Martinez
Thu Jun 14, 2012 12:36 PM

Post by Jessica Martinez on June 13, 2012

Hello Dr. Starkey,

you named 7-phenylhept-2-en-6-yne. Would 7-phenyl-2-heptene-6-yne also be correct?

1 answer

Last reply by: Robert Shaw
Sat Dec 10, 2011 10:07 AM

Post by NGAWANG TSERING on December 4, 2011

for this video i have been trying to forward by scrolling but its not working......cos iw ant to jump to ester part video but its not working...i tried a lot......

1 answer

Last reply by: Professor Starkey
Fri Oct 12, 2012 11:13 PM

Post by Jamie Spritzer on October 24, 2011

IUPAC name for tert-butylamine should be
2-methylpropan-2-amine

1 answer

Last reply by: Professor Starkey
Thu Oct 20, 2011 11:13 PM

Post by Leighann Bailey on October 8, 2011

are you familiar with a site that has many practice problems with answers?

1 answer

Last reply by: Professor Starkey
Sat Jul 30, 2011 12:01 AM

Post by Costa Sakellariou on July 18, 2011

How can i move around backwards and forward?
Can you please help?
Thank you.

1 answer

Last reply by: Professor Starkey
Wed Apr 6, 2011 11:32 PM

Post by Billy Jay on March 15, 2011

For the example in 26:55, is there any particular reason the compound wouldn't be named: 1-(1,2-dimethyl-4-butyne)-benzene as opposed to 3-methyl-4-phenyl-1-pentyne?

2 answers

Last reply by: Professor Starkey
Wed Apr 6, 2011 11:33 PM

Post by Billy Jay on March 15, 2011

Correction @ 11:20

2-propyloctene not 3-propyloctene

1 answer

Last reply by: Professor Starkey
Sun Feb 6, 2011 1:56 PM

Post by yasser algoufily on December 3, 2010

26:55 she made a mistake in numbering; there should be 5 carbons in the longest carbon chain not 6

Nomenclature

Draw all the products and select the major product for this reaction:
  • Loss of β2 H
  • Loss of β2 H
    Arrange these Alkene in order of increasing stability:
    Draw the product formed for this reaction:
    What is the major E2 elimination product formed:
    Draw the major alkene product formed for this compound in an E1 reaction:
    Draw the organic products formed in this reaction:

*These practice questions are only helpful when you work on them offline on a piece of paper and then use the solution steps function to check your answer.

Answer

Nomenclature

Lecture Slides are screen-captured images of important points in the lecture. Students can download and print out these lecture slide images to do practice problems as well as take notes while watching the lecture.

  • Intro 0:00
  • Cycloalkane Nomenclature 0:17
    • Cycloalkane Nomenclature and Examples
  • Alkene Nomenclature 6:28
    • Alkene Nomenclature and Examples
  • Alkene Nomenclature: Stereochemistry 15:07
    • Alkenes With Two Groups: Cis & Trans
    • Alkenes With Greater Than Two Groups: E & Z
  • Alkyne Nomenclature 24:46
    • Alkyne Nomenclature and Examples
    • Alkane Has a Higher Priority Than Alkyne
  • Alcohol Nomenclature 29:24
    • Alcohol Nomenclature and Examples
    • Alcohol FG Has Priority Over Alkene/yne
  • Ether Nomenclature 36:32
    • Ether Nomenclature and Examples
  • Amine Nomenclature 42:59
    • Amine Nomenclature and Examples
  • Amine Nomenclature 49:45
    • Primary, Secondary, Tertiary, Quaternary Salt
  • Aldehyde Nomenclature 51:37
    • Aldehyde Nomenclature and Examples
  • Ketone Nomenclature 58:43
    • Ketone Nomenclature and Examples
  • Aromatic Nomenclature 1:05:02
    • Aromatic Nomenclature and Examples
  • Aromatic Nomenclature, cont. 1:09:09
    • Ortho, Meta, and Para
  • Aromatic Nomenclature, cont. 1:13:27
    • Common Names for Simple Substituted Aromatic Compounds
  • Carboxylic Acid Nomenclature 1:16:35
    • Carboxylic Acid Nomenclature and Examples
  • Carboxylic Acid Derivatives 1:22:28
    • Carboxylic Acid Derivatives
    • General Structure
  • Acid Halide Nomenclature 1:24:48
    • Acid Halide Nomenclature and Examples
  • Anhydride Nomenclature 1:28:10
    • Anhydride Nomenclature and Examples
  • Ester Nomenclature 1:32:50
    • Ester Nomenclature
    • Carboxylate Salts
  • Amide Nomenclature 1:40:02
    • Amide Nomenclature and Examples
  • Nitrile Nomenclature 1:45:22
    • Nitrile Nomenclature and Examples

Transcription: Nomenclature

Welcome back to Educator.0000

We've already had a brief introduction on how to name alkanes; some basic IUPAC rules; methane, ethane, propane, and so on.0003

Let's take a look at some more complex alkanes and cycloalkanes and a variety of other functional groups we will encounter.0010

If we have a ring in a compound, we call those cycloalkanes; we simply take the name of that alkane and we put the prefix cyclo- before it to indicate that those carbons are forming a ring.0018

If there is a single group that is attached, if it is a mono-substituted ring, then we assume that the point of attachment is carbon number 1, defined as carbon number 1.0031

Because when we have a carbon chain... when we have a carbon chain, we have to decide which end to number from.0040

But when the carbons are in a ring, any carbon within the ring can be carbon number 1; we have to decide which one to assign as number 1.0046

For this first example, we have a five-membered ring; a five carbon alkane is called pentane; so this is called cyclopentane.0054

Then we take... that is our parent; then we alphabetize and number our substituents as usual and put them out front.0066

We have a two carbon chain here; that is an ethyl group; this is simply called ethylcyclopentane, all one word.0073

There is no number that needs to be drawn because any place you put the ethyl on that ring, you are going to get the same compound; so this is called ethylcyclopentane.0082

If we have two more groups, now we have to decide which carbon is defined as carbon number 1.0092

If there is one carbon with two groups on there, then that would be the best place to assign as number 1 because then we would have two groups at position number 1.0097

Remember we always want to get the lowest possible numbers that we can; so we will define that as carbon number 1.0107

Now we have to decide, are we going to number in a clockwise fashion or counterclockwise?0112

We want to number in the direction closest to the next substituent so that that substituent gets as low a number as possible.0117

Let's number here in a counterclockwise, this direction; two, three, four, five, six; this is a cyclohexane parent; cyclohexane.0123

We have a fluoro and a methyl and then this group is a little more complex than a simple methyl, ethyl, propyl, that sort of thing; how would we name that?0139

We have some instruction here; to name a complex substituent, we need to define the point of attachment to the parent as carbon number 1.0151

Then we perform a second, like a little mini IUPAC, to describe the name of that complex group.0159

For example, this is the group that... this is the point of attachment; so this has to be described as carbon number 1 for this substituent.0165

Then we ask what is the longest carbon chain from that point on?--we see that we can have a three carbon chain here; this is actually a propyl group.0174

But it is more than just a propyl; what does it have on carbon 1?--it has a methyl group; we are going to describe this as a... this whole group is described as a 1-methylpropyl.0184

That is how we will handle more complex substituents; now let's alphabetize these and list them in the proper order; the fluoro comes first so we have a 1-fluoro.0200

Then methyl comes before methylpropyl; just like if you look that up in the dictionary, the shorter word would come next; we have a 1-methyl.0211

Then at carbon 3, we have this big whole group; what we do is we write a 3, and then in parentheses, we write this big name of the complex group.0220

Let's see if I can not completely run out of room; we have a 1-methylpropylcyclohexane.0229

How about this last case?--we have a four-membered ring; we call that cyclobutane.0241

Here we have two groups; we have to decide now which one should be carbon 1 because we could either have 1,2 or 1,2; we would get the same set of numbers either way that we numbered it.0250

In that case what we do is the carbon bearing the group that comes first alphabetically is assigned number 1.0263

That way the substituents are listed alphabetically and the numbers are listed in increasing order.0271

What we have here is a methyl; then this is going to be a longer word; we will have that next.0277

You know what?--let's make this an ethyl... sorry... so this comes first alphabetically; we will just change that.0285

This is... we will do one and two and three and four; this is another complex substituent that we are going to have to name.0293

It looks like a t-butyl group; that would be nice if we were allowed to use a common name; we could just describe it as a t-butyl.0302

But an IUPAC name can't use that term; so instead we go through our rules again; now this is carbon number 1; what is the longest carbon chain from that point on?0308

No matter which direction you go, the most you can have is two carbons; so this is actually an ethyl group.0320

But it not just an ethyl; it has a methyl here on carbon 1 and another methyl on carbon 1; what we are going to call this is a 1,1-dimethylethyl.0327

This is the IUPAC name for the t-butyl group; it is a 1,1-dimethylethyl; and where was this whole group?--this whole group was on position 2.0345

On position 1, we had an ethyl; we could double check, see how we alphabetized e- comes before m-; when we go to alphabetize, we ignore the prefixes like di- and tri-.0357

So we have a 1-ethyl-2-(1,1-dimethylethyl)cyclobutane; we have the ring for the cyclo; we have the four carbons.0372

Bit by bit, step by step, in a systematic way, we are going to build these complex names up.0383

If we have a carbon-carbon double bond in a structure, those compounds are called alkenes; the way we are going to name them is we are going to look for the longest carbon chain.0390

But that longest carbon chain must include both carbons of the carbon-carbon double bond; it is no longer just where is the longest carbon chain throughout the whole structure?0399

Now that we have a functional group in the molecule, we need to incorporate that functional group into the parent; so the longest carbon chain must contain both carbons of the carbon-carbon double bond.0407

Then we are going to number from the end that is closer to the carbon-carbon double bond so that the double bond will get the lowest number possible.0418

After doing that, what we are going to do is we are going to take the ?a in the word alkane, methane, ethane, propane, butane, and we are going to change it to an -e.0427

We are going to call it an alkene instead; and we are going to put a number out front that tells the reader where the double bond starts--what is the first carbon of that carbon-carbon double bond.0436

We are going to call it a #-alkene or you can insert that number inside the name; this is actually the preferred way for IUPAC.0447

But I think it is a little more difficult for beginning students to look at that convention.0456

For example, our simplest alkene is a two-carbon alkene; he has a common name; this is called ethylene; ethylene is a gas that is generated by fruits in the ripening process.0463

Ethylene is actually sprayed on fruit to help them ripen when they are picked earlier for packaging and for handling.0473

This is commonly known as ethylene gas; but the IUPAC name, it would be an ethane derivative because it is two carbons; instead of calling it ethane, we call it ethene.0481

Not a big difference between the common name and the IUPAC name; but the IUPAC name is ethene; this tells the reader... that E tells the reader that there is a double bond in this molecule.0496

In this case, I don't need to indicate where the double bond is because there is only one place for it to be--connecting those two carbons.0506

This compound is commonly known as allyl chloride because you have a chlorine that is allylic--next to a double bond.0512

It is known as allyl chloride; but let's do its IUPAC name; we have our three carbon chain is right here; that is our only possibility for our longest carbon chain.0519

When we go to number it, we are going to number it from the end closest to the double bond; we will start from this end; one, two, three.0528

Three carbons means it is a propane derivative; because of the double bond, we call it propene; this is 1-propene.0538

We are going to indicate the first carbon of the carbon-carbon double bond; this implies that there is double bond starting at 1 and going to 2.0547

What else do we have on here?--we have a chloro group at carbon 3; so this is 3-chloro-1-propene; remember there is dashes between numbers and letters.0555

Sometimes we leave off the 1; in this case, that might be implied; but it is a really good habit to leave that 1 in there.0569

We don't want to make that assumption then make a mistake; so this would be the best name for that.0576

How about this case?--where is our longest carbon chain that contains both carbons of the double bond?0582

It looks like we will come across here but then we will move down in this direction because that would be a longer chain than over here.0588

How are we going to number it?--if we numbered it from here, our double bond would start at carbon 2.0596

If we numbered it from here--one, two, three four, it wouldn't start till carbon number 4.0601

We would rather have it be at carbon 2; one, two, three, four, five, six; a six carbon alkene is going to be called hexene; it is a 2-hexene.0605

By circling off and blocking off the parent, it is very easy for me to see what other groups are attached.0622

We still have this two-carbon group; that is called an ethyl group; at carbon 3, we have an ethyl.0628

How about this next case?--our longest carbon chain would be this one; but the longest carbon chain containing the carbon-carbon double bond would be down here.0638

We have to make sure to include that; and how long is that?--one, two, three, four, five, six, seven, eight carbons; that is an octane derivative; we are going to call this 1-octene.0647

At carbon 2, we have a one, two, three carbon chain; that is a 3-propyl; 3-propyl-1-octene.0663

We can incorporate a double bond into a cyclic structure as well; remember, with a ring, we have to decide where to start numbering our carbon chain.0673

One of the double bond carbons is going to be carbon number 1; we are going to have to number through the carbon chain and then continue on to also give the substituent the lowest possible number.0685

If I numbered from here, one, two, three, four, five, six, the substituent wouldn't be until position 6.0695

If I numbered this way, one, two, three, I get the lowest number for the double bond; that has to be at carbon 1; then I also get the substituent at the lowest number.0702

Four, five, six; this is a six-membered ring; we would call that cyclohexane because it is a ring; because it has a double bond, we call it cyclohexene.0712

Where is our group?--what is this group called?--the benzene ring is called a phenyl group; we have a 3-phenylcyclohexene.0725

Here is a case where we really don't need the number; the double bond has to be between carbons 1 and 2; that is how you define a ring.0734

There is no other place to put the double bond since that is our highest priority; if you want to put that in there just to be safe, that probably won't hurt if you want.0741

What if we have two double bond?--if we have two double bonds, we are going to indicate both numbers of where the double bonds start.0751

We are going to call it a diene or a triene or a tetraene and so on; so we are going to include that, we are going to put that in there.0758

Again, we want to give our double bonds the lowest possible number; and I need to give both double bonds the lowest possible number.0768

The only way to number this to give the double bonds the lowest possible number would be as so; one, two, three, four, five.0778

What do we have on carbon 5?--we have a bromo; we have another 5-bromo; we are going to call that a 5,5-dibromo... a 5,5-dibromo.0787

Then at carbon 1 and carbon 3 is where we have our double bond starting; this is a 1,3-cyclopentadiene.0797

Notice we stick that -e back in; it would be called cyclopentene, but when we have the diene or the triene, we put the -a back in just because it is easier to read that way.0812

So it is called cyclopentadiene or hexadiene or some such thing.0822

Another thing that we need to be concerned with with double bonds is the fact that we can have stereochemistry associated with the double bond.0830

Where if we have two groups... remember we have cis or trans as a relationship that those double bonds can have; all the examples here don't have that shown.0837

This molecule can have cis-trans isomerism, but I haven't shown one particular stereoisomer; I haven't shown the geometry of this molecule.0848

I have drawn this as a linear molecule with these bonds hanging straight down; we wouldn't be able to tell which stereoisomer I was dealing with here.0857

When you have a double bond in a ring, in a five or six-membered ring, that double bond has to be cis.0866

Those two alkyl groups have to be pointing in the same direction in order for them to reach each other and form a small ring.0872

So this must be cis if you are looking at a seven or fewer... for small rings, let's just say... for small rings.0879

So we don't say that it is cis-cyclohexane because there is no such thing as trans-cyclohexane; it would be impossible to build that.0892

Let's take a look at some examples that do have stereochemistry involved because we are going to want to include that as part of the name.0901

If you have an alkene simply with two groups and two hydrogens, then we could describe those two groups as being cis or trans.0909

Cis means they are on the same side; trans means they are on opposite sides.0917

For example, we have an alkene here; let's number from the end closest to the alkene; one, two, three, four, five, six; this is hexene; this is 2-hexene.0926

But one particular stereoisomer is shown of 2-hexene, where the two alkyl groups are pointing on the same side; we are going to describe this as cis-2-hexene.0937

We are going to put that stereochemistry all the way out in front of the name to describe the stereochemistry of the double bond.0948

Here is another example; we have this in a ring; one, two, three, four, five, six, seven, eight, nine, ten; this is a ten-membered ring.0955

We would call this a cyclodecane if it was an alkane; because it has a double bond, we call it cyclodecene.0966

In this case now, we have one carbon group pointing this way and one pointing this way... let's write the name first, sorry... cyclodecene.0975

But in this case, the two carbon groups are not pointing in the same direction; they are pointing in opposite directions.0989

If you want to look at the hydrogens to confirm that, you drawn in those hydrogens for those trigonal planar carbons.0994

You see that in fact they are pointing in opposite directions; so this is an example of trans-cyclodecene.0999

If we had looked at this molecule instead, if the double bond were here, this would be an example of cis-cyclodecene because those two carbon groups are pointing in the same direction.1006

When stereoisomers can exist, we need to look carefully at the three-dimensional picture that is shown to decide which stereoisomer it is that we are trying to name.1020

Here is another example; now we have three alkenes; let's number from here so we get the lowest numbers possible--one, two, three, four, five, six, seven.1031

Seven carbons is a heptane; when we have three double bonds, we call this heptatriene; where are those three double bonds?--they start at 1 and 3 and 6.1041

If it is a triene, we need to have three numbers out front; the triene, one, two, three, tells us where those three double bonds are.1057

Is there any stereochemistry in this problem?--there can't be any stereochemistry on this first or this last one because there is only one group attached.1068

But look at this middle one; there are two groups attached; what is the arrangement of those two groups?--they are on opposite sides; this is trans.1076

Sometimes we might miss that; if it is a line drawing and it is obviously drawn in the same side, then we might notice that it is cis.1084

But when we leave it in its regular zigzag notation, sometimes we might miss that that must actually be the trans isomer that is shown; this is trans-1,3,6-heptatriene.1090

I don't need to say which double bond is trans because it is the only double bond that can have stereochemistry.1101

If we only have groups, we can use the word cis and trans; if we have more than two groups, the term cis and trans doesn't mean anything more.1108

Cis means the two groups are on the same side; trans means the two groups are on the opposite side; if I have three groups on the alkene, the term cis and trans is now ambiguous.1116

We need to learn new terms to describe those stereochemistries; the new terms we have are going to be E or Z.1125

Z is what means the same side; so if we are similar to cis, we are going to call it Z; and E means opposite sides.1134

Where do these letters come from?--E and Z, they come from German words; if you speak German, you will have no trouble remembering these rules.1149

If you are like me and these words are not familiar to you, then you need some kind of way to remember which is E and which is Z and what do they mean.1156

I have a little mnemonic that I came up with that I will share with you; see if that helps.1165

Here is how we assign it; what we do is we look at one carbon at a time and we assign the priorities to those two carbons.1172

We are going to use the same... we are going to prioritize them based on simply their atomic number.1180

We are comparing a chlorine to a carbon; chlorine has a higher atomic number so chlorine is a higher priority than carbon.1186

Then we go to the second carbon and we do the same ranking; carbon versus hydrogen; carbons wins; it is a higher priority, higher atomic number; that is also number 1.1194

We ranked them 1,2 and 1,2; now what we do is we compare the number 1 groups and we ask: are those number 1 groups on Zis same side?1205

If we say it with a little crazy accent, then we remember that Zis same side means that it is the Z stereochemistry.1215

In other words, since these number 1 priority groups are cisoid to each other, we are going to describe this molecule as being the Z stereochemistry.1221

We put that all the way out in front in parentheses; this is italicized as is the cis and trans are italicized, you see when they are in print; this is going to be called (Z)-2-chloro-2-butene.1230

The other stereoisomer, if I swap the chlorine and the methyl, the chlorine and the CH3, now you see that my number 1 priority group is here and my number 1 priority group is here.1241

Now they are transoid to each other; we ask: are the higher priority groups on Zis same side?--they are not; now it is the opposite of Z; it is E.1250

We need to remember what both of those names are; of course, the more you work with these, the more you will become familiar with which is which; this would be called the E isomer.1258

Let's just take a look at a couple quick examples here; how would we name this alkene?--the longest chain that contains the double bonds is right here.1267

What side do we number from?--one, two, three; one, two, three; this is a case where we would we have a tie for the double bond.1279

How do we break that tie?--now we want to consider the substituents and try and give them also the lowest possible number.1288

We will number from the end closest to the first substituent; one, two, three; this would be the better direction to go, the correct direction to go.1294

This is a six carbon chain; we call that hexene; the double bond starts at carbon 3 so we call this 3-hexene.1304

What else does it have attached?--we have a methyl and a methyl and a methyl; we group those all together; we call this a 2,3,4-trimethyl.1315

Sorry, I ran out of room here... 2,3,4-trimethyl-3-hexene; which isomer have we shown?1330

Again, I can't... what does the word cis mean here?--or trans?--it has no meaning; we have to define it as E or Z.1336

What we do is we break the double bond in half; we look at one carbon at a time.1343

This carbon... we are comparing a carbon and a carbon; that is a tie; how do we break the tie?--we are going to move the next atom and so on until we find a difference.1348

This has three hydrogens attached; this has another carbon attached; this group wins; this is number 1; this is number 2; in other words, an ethyl beats a methyl.1357

Over here, we have again a tie--carbon versus carbon; but this carbon just has three hydrogens on it while this carbon has two other carbons attached; this is number 1 and this is number 2.1368

Which isomer do we have here?--do we have E or Z?--we compare the number 1 groups; are they on Zis same side?--they are not; they are on opposite sides.1382

We call that the E stereochemistry; that goes all the way out front; we describe this as E.1391

How about last one?--what is our longest carbon chain?--we have to come down in this direction to find the longest carbon chain containing the two carbons.1398

We will number from this end to give the double bond on carbon 2; this is a pentene derivative; it is pentene; it is 2-pentene.1408

We also a chloro and a methyl; who will come first?--we will do alphabetically; 1-chloro-3-methyl.1425

Finally, do we have stereochemistry?--we need to check every time; is there stereochemistry in this case?1436

There is because we have three different groups on here; if I flip these two groups around, it would be a different isomer; it would be a different compound.1441

How do we describe this isomer in its name?--we rank the two groups on carbon 3; we have a methyl and an ethyl; we have done that ranking before; the ethyl is the higher priority.1449

What are the two groups on carbon 2?--we have a carbon and a hydrogen; there is just a hydrogen here; so this chloro substitute group is the higher priority.1461

Here we see our two higher priority groups are on Zis same side; they are on the same side; they are cisoid to each other; we describe it as the Z stereochemistry.1471

When we have a carbon-carbon triple bond in a molecule, we call it an alkyne; we are going to very much follow the same rules we did for alkenes.1488

Except instead of replacing the -a in the alkane, we are going to replace it with a -y instead of with an -e; we are going to name it as an alkyne.1495

Once again, we have to put the number out in front or insert it in the middle to say where the triple bond is on the carbon chain.1505

We are going to try and give the triple bond the lowest number possible; if we had two or three or four alkynes, we would call it a diyne or a triyne or a tetrayne.1514

Let's again look at some simple examples; this is the simplest alkyne; it is called acetylene; that is another fuel; acetylene is what is used in torches, very hot burning fuel.1527

This is called acetylene; its IUPAC name, since it is two carbons, means it is an ethane derivative; we are going to call this ethyne.1537

We are going to call it ethyne or acetylene--is another name that you should be familiar with.1547

The word propargyl means next to a triple bond; just like we use the word allylic to mean next to a double bond; propargyl means it is next to a triple bond.1553

This could commonly be known as propargyl bromide; but let's do its IUPAC; we have a three carbon chain in this case; numbering to give the triple bond the lowest number.1566

This is a propyne derivative; it is 1-propyne; at carbon 3, we have a bromine; we are going to call it 3-bromo; 3-bromo-1-propyne.1576

How about this case?--what is our longest carbon chain?--longest carbon chain will go here and here and don't be fooled by this CH3 group.1593

I am not going to stop at the end of this carbon chain because my carbon chain is not done; it extends up here.1602

There is actually a one, two, three, four, five, six carbon chain here, with a triple bond at carbon 1; we are going to call that a 1-hexyne... a 1-hexyne.1608

What else do we have?--we have a methyl and we have a phenyl... we have a phenyl; which comes first?--L-M-N-O-P, methyl comes first; so we have a 4-methyl and a 5-phenyl.1621

That is our hexyne; if we have multiple double bonds and triple bonds, our names get pretty ugly pretty quickly.1639

Here we can number one, two, three, four, five, six, seven, eight; it is an octane derivative; but we have a double bond at 1 and 6; it is an octadiene; plus we have a triple bond at carbon 3.1646

Here we have to... because we have two different functional groups in the same molecule, we have to break the name up and insert the number right before the suffix it is modifying.1663

This means I have a triple bond at carbon 3 and my diene is at carbons 1 and 6, starting at 1 and 6.1674

Or you could break up the name more completely and insert the numbers in both cases immediately before the functional group that they are representing, that they are defining.1684

Either one of these is fine; but the one where the numbers are inserted are becoming increasingly more common.1700

If you have to make a choice between an alkene and an alkyne, who gets the lower number?--it is the alkene that wins.1707

In this case, when we look at our longest carbon chain right here, we want to number from this end so that the double bond gets the lowest number possible.1713

Then the triple bond just ends up where it ends up; this is a seven carbon chain; what do we call that?--that is a heptane derivative.1726

But now we have an ?ene and an ?yne; let's break up the name; we have a hept-2-ene and then a 6-yne; hept-2-ene-6-yne.1734

We also have a phenyl group here on 7; we can throw in a 7-phenyl; then that continues all one word hept-2-ene-6-yne.1754

If you an OH on a carbon chain, we are going to describe that molecule as an alcohol; that is going to define the parent chain.1766

It is going to be the carbon containing... the chain which contains the carbon bearing the OH group; and it is going to be named as an alcohol.1776

We will find the longest carbon chain that has the alcohol attached to it; and we are going to number from the end closest to that alcohol so that that alcohol gets the lowest possible number.1785

What we are going to do is we are going to drop the ?e at the end of the name and we are going to add a new suffix; we are going to put the ?ol at the end of it.1795

So it is going to be called methanol, ethanol, propanol, and so on.1805

We need to also put a number out in front to tell the reader where along the carbon chain that OH group resides.1809

Once again, you can sometimes see the number inserted immediately preceding the suffix so that it is no question to what the number refers.1817

For example, this looks like the isopropyl group, when we have three groups and attached at the middle; this is called isopropyl alcohol.1828

You may have heard of that compound; that is used as rubbing alcohol; it is an astringent; you can use that as a cleaning agent.1835

You might find that in your medicine cabinet for facial cleaners and such.1842

Isopropyl alcohol, that is the common name for this; its IUPAC name would follow the rules described above--longest carbon chain containing the OH group; the OH defines our parent.1847

It doesn't matter in this case which way we number it because both of them would put the carbon bearing the OH as the carbon 2.1862

We are going to call this 2... instead of propane, it is propanol... propanol.1870

We dropped the -e and we replaced it with an ?ol; the number 2 tell us where that alcohol is, where that hydroxyl group, that OH group is.1876

Here is another example; we have a four carbon chain; now we would have to number it in this direction to give the OH the lowest possible number.1887

This is called a... it is four carbons so it is called 2-butanol; but this also has a common name.1895

What does this arrangement look like?--when we have a four carbon chain and we've attached something at the second carbon, the secondary carbon?--we call this sec-butyl.1902

This could also be called sec-butyl alcohol; those common names just give us a picture so quickly that it is really useful to be familiar with them.1911

How about this case?--we have a couple OHs; this is where we are going to now call it a diol; our longest carbon chain must contain both OHs.1926

Once we find an OH on our structure, we have to... that defines our parent carbon chain; it is no longer just about finding the longest carbon chain; that is if all we have is an alkane.1937

Let's go up here; it looks like that is the longest carbon chain that contains our two OHs.1948

We will number it to the end closest to the first OH; we will number down here one, two, three, four, five so that we have an OH at carbon 1.1955

Let's see, a five carbon alkane is called pentane; with one OH, we would call it pentanol; with two OHs, we call it pentane diol.1965

Notice we add the -e back in; we actually at the ?e back in because it is easier to read that way than just saying pentandiol; that would be difficult; so it is called pentane diol.1975

We have to tell everyone where these OHs are; they are at 1 and 4; these numbers tell us where to find the OHs.1989

What else do I have on this chain?--I have a 3-methyl; and I have a one, two, three, four, five, six; I have a hexyl; that comes first; we have a 2-hexyl and a 3-methyl... 1,4-pentane diol.2002

Once I see an OH on our chain, that is going to have the highest priority number; I no longer care where the double bond or triple bond is; I always want to make sure my OH gets the lowest possible number.2023

For example, in this ring, since any carbon can be carbon 1, we have to decide which is carbon 1; it is the carbon bearing the OH; that must be carbon 1.2034

Then we are going to number again either clockwise or counterclockwise to take care of the rest of the functional groups.2044

Of course, now we will number in a counterclockwise direction so that the double bond gets the lowest possible number.2049

This molecule is called 2-cyclohexene-1-ol; the 2 refers to the double bond and the 1 refers to the OH group.2056

Again, when you have two functional groups with numbers on them, it is sometimes a little clearer to break up the name and insert both numbers directly into the name.2066

But you clearly have to break it up a little bit; otherwise, you can't just put the 2 and the 1 out in the front, because then you wouldn't know which number describes which functional group.2077

We have to break up the name at least this much; and you insert a number immediately before the suffix.2085

How about this next one?--longest carbon chain is right here; how do we number it?--which end do we number it from?2094

I don't care what number the triple bond gets; I care instead what number the OH gets so I am going to number from this direction; one, two, three, four, five.2104

Let's see, five carbons would be a pentane; the triple bond makes it a pentyne... pentyne; this is where the triple bond changes this middle letter.2116

Because of the OH, we call it a pentyne-ol; let's put the 2 in here so we know where that alcohol group is; and the triple bond was at carbon 4; this is 4-pentyne-2-ol.2130

Or you could say pent-4-yne; the triple bond starts at carbon 4; -2-ol; the suffix always goes at the end; the ?ol is always the very last thing that you have.2145

We take care of all this parent stuff; then we list out front everything else that is attached.2159

We have already handled the OH; we've already handled the triple bond; the only thing left is this methyl group at carbon 2; we alphabetize all those, put them out in front.2164

Notice how we keep building on these systematic IUPAC rules; so it is really important to get that foundation down of your alkanes.2175

Then gradually build on them with each new functional group so that you can see how they work together when you have multiple functional groups in the same structure.2183

If you have an ether in your compound, an ether means that we have an oxygen attached to two carbons.2194

An ether is not something that changes the parent name like an alcohol does; we are not going to learn a new suffix for it.2201

Instead, it is simply a substituent that you might find attached to the parent; it is just a group; how do we name that group?2208

If we have an OR group hanging off of a parent, normally we would call that R group, have a -yl ending like a methyl, ethyl, propyl.2215

What we are going to do is we are going to change that -yl and we are going to make it ?oxy instead; instead of ethyl, we have ethoxy; so we have ethoxy, propoxy, butoxy, and so on.2224

If we have very simple ethers, sometimes we just use common names by listing the two alkyl groups on either side; again it is nice to be familiar with the common names; but that is not IUPAC.2237

For example, this could be named isobutyl ethyl ether as a common name because it has an isobutyl on one side, has an ethyl on the other side.2250

That is one name for this ether; but let's see how we would do it by IUPAC.2260

With an ether, what we have to decide is of the two alkyl groups on either side, or the two carbon chains on either side of the oxygen, which one is going to be the parent.2264

We are going to look for either one that has a functional group on it or one that is a longer carbon chain; here they are both just alkanes so we will go on this side with the longest carbon chain.2272

Here is our longest carbon chain; now it is an alkane; so we treat it like any alkane; we are going to number it so that the substituents get the lowest possible number.2283

We will number from this end; one, two, three; this is a propane derivative; what does that propane have on it?--it has a methyl.2291

Then this group, what do we call this group?--it has one, two carbons, plus an oxygen; we are going to call that an ethoxy group; this is an ethoxy group.2301

Then we alphabetize it just as usual; ethoxy comes before methyl; so we have a 1-ethyoxy-2-methyl; pretty complicated name for this molecule.2312

You can see why we might prefer to just call it isobutyl ethyl ether because that gives a much quicker picture to those who are familiar with those common names.2324

How about this guy... I'm sorry, I skipped some information on that previous slide; it pointed out that these aromatic groups, the benzene with an OH is called phenol.2336

This parent could be named as phenol; the OH is defined as carbon number 1; in the 3 position, we have a methoxy group; this is called 3-methoxyphenol.2351

This compound is called diethyl ether as its common name; again just two ethyl groups attached to an oxygen; that is usually how we describe this molecule.2370

But what would its IUPAC name be?--you have to pick one of those ethyl groups to be your parent; it is no longer an ethyl group; it is now ethane as your parent.2379

What does that ethane have attached to it?--it has an ethoxy group; ethoxyethane.2391

What if we have an OH and an ether again?--how do we decide who has priority and where do we go for the parent chain?2405

Again, as soon as you see that OH, that means your molecule is an alcohol and that carbon attached to that OH has to be your parent.2413

Let's define that as our parent; here is our carbon chain containing the OH group; we will number it from this direction to give the OH the lowest possible number.2421

This is a 3-hexanol... 3-hexanol because it has an OH group; what are we going to call this group?--again, this is not a simple methyl, ethyl, propyl.2436

What we need to do is we need to figure out how to name this; what we are going to do is our little mini IUPAC here.2452

Remember, by definition, the point of attachment to the parent must be defined as carbon number 1; we number from there; one, two, three, four; this would be a butyl group.2459

But it is just not a butyl group; it has a 2-methyl; it would be called 2-methylbutyl.2472

But it not a 2-methylbutyl because we also have this oxygen; it is going to be called 2-methylbutoxy; it is a 2-methylbutoxy group.2479

Without this, it would just be a butoxy, but now we have a 2-methylbutoxy.2492

We put that all in parentheses and where is that entire group attached to the parent?--to carbon 5; step by step, we will build up these names.2497

Last case here, we have a triple bond; that is going to define our parent--any functional group that modifies the parent name; so instead of having ethane, now you have ethanol or ethene or ethyne.2509

Anything that modifies the name of the parent--double bond, triple bond, or an OH group; that is going to be your higher priority compared to any other ordinary substituent that you have.2524

This is an alkyne; we are going to name it as such; we will number it from here to give the lowest number possible; a four carbon alkyne is called butyne; this is 1-butyne.2534

What do we have attached here at carbon 3?--if this oxygen weren't here, we would call this cyclopentane group, we would call it a cyclopentyl group, right?2546

If it was just five straight chain carbon, we would call it pentyl; now that is called cyclopentyl.2557

With the oxygen, we call it cyclopentoxy... cyclopentoxy; where is this cyclopentoxy?--carbon 3; 3-cyclopentoxy-1-butyne.2563

If we have a nitrogen containing compound, we call those amines; as usual, we are going to find our parent chain that contains the nitrogen.2582

We are going to drop the ?e at the end of the name; we are going to add a new suffix; we are going to add the word -amine as our suffix.2592

It is going to be named as an alkanamine, ethanamine, propanamine, butanamine, so on.2598

It is possible for a nitrogen to have more than one alkyl group; one of those alkyl groups is going to be the parent; the other alkyl groups would be described as substituents.2605

Because they are attached to the nitrogen rather than a carbon chain, we don't give the number of the carbon; we just list a capital N to indicate where it is being substituted.2615

Again, we will find some common names; if it is a simple alkyl group, we will just call it an alkyl amine; we will see some examples of that.2626

We will also see some examples where maybe it is not the highest priority functional group.2634

For example, this amine has four carbons and a straight chain; it would just be called butyl amine or N-butylamine; that would be a common name for that.2639

But its IUPAC would be... longest carbon chain; one, two, three, four; it is a butane derivative; at carbon 1, we have an amino group, we have a nitrogen group; this is called 1-butanamine.2648

We've dropped the -e of butane and we've replaced it with the word ?amine; 1-butanamine.2665

This next one, we have two alkyl groups; one of them is going to be the parent; we will pick the longer one; this is our parent.2674

One, two, three to give the nitrogen the lowest possible number; this is propanamine; this is 1-propanamine.2681

But it is not just propanamine because it has on the nitrogen, it has an ethyl group attached; the way we are going to describe that is with a letter N; N-ethyl-1-propanamine.2691

Just like a number refers to one of the carbons in the carbon chain, a capital letter N, it is italicized, refers to the nitrogen in the compound as the location of the substituent.2703

When an NH2 is on a benzene ring, we call that molecule analine; we could use that as a parent name; you might come across that name.2716

This NH3 all by itself was called ammonia; that is not really an organic molecule; it has no carbons in there; but we will see ammonia a lot; you should be familiar with that name.2726

Let's see a few more examples; this is another one that has a very simple common name; how would you describe the alkyl group attached to the nitrogen in this case?2736

It is four carbons arranged, attached to the middle carbon; this is the t-butyl group; we could just call this t-butyl amine as a common name; t-butyl amine.2745

But its IUPAC name, we would have to follow the rules--find our longest carbon chain bearing the nitrogen.2758

That is right there; it is a three carbon chain; one, two, three; this would actually be propanamine.2766

What else does it have attached?--on carbon 2, it has a methyl group; we could call this 2-methyl; 2-methylpropanamine.2775

If we have an OH and an NH2, we have to decide which one is the higher priority because we can only have one suffix; we can't have an ?ol and an ?amine suffix.2787

The rule is that OH is the higher priority; we would have the same carbon chain in both cases; but in this case, now we are going to name it as an alcohol.2798

We want to give the OH the lowest possible number; so we will number from this direction; one, two, three, four, five, six.2815

This is a six carbon alcohol; we call hexanol; it is a 3-hexanol; remember the ?ol ending tells us there is an OH in the molecule.2822

Now we just simply name the NH2 group as a substituent, as a group hanging off; just like we have a methyl or a phenyl or a chloro.2835

What we call an NH2 group is an amino group; we have a 5-amino-3-hexanol; amino just like methyl or ethyl or propyl or bromo or chloro.2842

How about this one?--it looks like we can use that analine as the parent; analine; how is this different from analine itself?2859

It has a methyl group on the nitrogen and a methyl group on the nitrogen; as usual, we combine the common substituents all together.2872

Where are they?--it is a dimethyl, but they are both on nitrogen; we are going to call this N,N-dimethyl; N,N-dimethylanaline; that means each methyl group is on the nitrogen.2882

Here is an example; now we have an ether and an alcohol and a nitrogen; how do we handle this?--thus far, our highest priority group is the oxygen, the OH alcohol.2898

The longest... the highest priority group is the one containing... the parent chain is the one containing the OH; we give the OH the lowest possible number.2910

Everyone else just gets whatever number they end up with; this is actually a propanol; 1-propanol derivative; what do we have attached to it?2920

This is a one, two, three carbon chain; we would call that a propyl; but with the oxygen, we call it a propoxy.2933

Here, if it was just a nitrogen, we would call that an amino group; but it has something else attached to it; what is attached to it?2942

It has a phenyl attached to it; just like IUPAC, this is not... we just do a little IUPAC here; instead of just amino, it is a phenylamino.2950

We don't have to locate the position of it because it is just one atom; it has to be attached to the nitrogen.2960

That would come first alphabetically; we will list that first; 2-phenylamino and then 3-propoxy-1-propanol.2969

A little bit more about amines; we could describe an amine as alkyl or aryl depending on the type of carbon group that is attached.2987

If you have a benzene ring attached, we would call it an arylamine; otherwise, it is an alkylamine.2995

We can also describe the amine as being primary, secondary, tertiary, or quaternary; we define it by describing how many carbon groups are attached to the amines.2999

A primary amine, which we designate with this 1° sign, that means primary, means we have just one R group; then it is an NH2.3011

Remember nitrogen likes to have three bonds and a lone pair to be neutral.3019

Because this has just one alkyl group, it is described as a primary amine; this would be methylamine or methanamine would be the IUPAC.3023

But if we had two alkyl groups attached, like two methyl groups here, we describe it as a secondary; it is just an NH group.3032

Here we see our two alkyl groups; we would call this diethylamine as the simplest name; here is the IUPAC; you can check that; N-methylmethanamine would be its IUPAC name.3041

Tertiary is what we have when we have three alkyl groups or aryl groups, three groups attached to the nitrogen.3052

This is called triethylamine--would be a common name for this; that is usually how we call it because look how big and awful the IUPAC name is; that is called a tertiary amine.3060

It is even possible to have four bonds to nitrogen; but any nitrogen with four bonds is now going to be a charged nitrogen; this is called a salt.3070

It is called a quaternary ammonium salt; this is called tetramethylammonium iodide; ammonium means we have an N+.3082

So it is possible to have even four groups on a nitrogen; but that is going to be an ionic compound.3090

Let's move into compounds that have carbonyls, C-O double bond; the carbonyl is what we call a C-O double bond; there are many functional groups that contain carbonyls.3099

The first one we will talk about is an aldehyde; an aldehyde has the formula here, RCHO; we have a carbon chain on one side and a hydrogen on the other; that is described as an aldehyde.3111

When we have an aldehyde, we are going to find the longest carbon chain that starts at the carbonyl; because there is a hydrogen here, the carbonyl is necessarily at the end of a carbon chain.3127

We start from here and we count our longest carbon chain; the carbonyl carbon is always carbon number 1; we don't say that it is... we don't list it as carbon 1; that is the definition of an aldehyde.3138

What we are going to do is we are going to drop the -e of the alkane name and we are going to add the suffix ?al; it is going to be called an alkanal.3151

The ?AL ending means we have an aldehyde; notice how close that is to an -ol ending we saw for the alcohol.3161

It is very important to have neat penmanship when you are doing these nomenclature problems because the difference of a single letter can mean a right or wrong answer or a totally different structure.3167

As I mentioned, no number is given to indicate where the carbonyl is.3178

Our simplest carbonyl is right here, simplest aldehyde actually; it has a hydrogen on both sides; that is the simplest aldehyde; he is called formaldehyde.3183

If you have ever worked in a biology lab, you are familiar with formaldehyde because this is used as a preservative for dead tissues if you ever dissected a frog or something.3192

That smell that is associated with that is the formaldehyde coming from that preservative solution.3201

This is the simplest case, just a single carbon; that means it is a methane derivative; what do we call this?--we drop the ?e from methane and we add the letters ?al; this is called methanal.3208

Methanal means I have an aldehyde; but almost always this is called formaldehyde instead; it is such a common name.3221

This one where we have the next simplest aldehyde--has just a methyl group on one side; he is known as acetaldehyde; we are going to see this acet common name pop up again and again and again.3228

This acet group or the Ac group represents a carbonyl and a methyl group attached; a COCH3, a carbonyl with a methyl group attached.3240

Because this is the aldehyde derived from this acetyl group, we call this acetaldehyde; we are going to see this name pop up again and again.3252

But that is its common name; what would its IUPAC name be?--longest carbon chain; we have two carbons; one, two; instead of ethane, we have ethanal.3260

Notice there is no number; we don't say 1-ethanal; that is impossible; it is just called ethanal because the carbonyl has to be a carbon number 1.3271

Here is a more complicated molecule; here is our parent; we must number this way; one, two, three, four; this is a butanol.3281

I have already shown that the carbonyl is the higher priority because that is the fact; the prioritization of functional groups is based on oxidation state.3292

A carbon with two bonds to oxygen is going to be a higher than one with one bond to oxygen; any carbonyl is going to beat out an oxygen, be a higher priority.3301

So we are no longer going to name this molecule as an alcohol; we are going to name this as an aldehyde; now we have to deal with this OH group simply as a substituent.3312

What are we going to call it?--we are going to call it a hydroxy group; we are going to call it a hydroxy group.3322

At carbon 4, we have a hydroxy; this is called 4-hydroxybutanol; notice it is not hydroxyl; there is no -l there; it is just hydroxy.3329

This is benzaldehyde; the aldehyde that is derived from benzene; it is called benzaldehyde; what would its IUPAC be?--let's see if we can come up with that.3341

What is our longest carbon chain containing the carbonyl?--there it is, just one carbon; this is actually a methanal derivative.3351

What does it have attached?--it has a phenyl group; you could call this phenylmethanal.3359

We wouldn't find it named that way very often; but it is important to know both the common names and the IUPAC names.3368

A lot of times, if you go to a chemical supplier catalog and you are looking it up, sometimes it is just as likely to be listed in its IUPAC name as its common name.3372

So it is really important to go back and forth; a lot of times, you pick up a reagent bottle in the lab, and it might have the common name rather than the IUPAC name.3383

That is why they are stressed so often; it is a short list of common names; you do want to be familiar with them so that you can communicate properly.3391

How about this last one?--this is carbon 1; it has to be part of our parent chain; this is where our parent chain starts.3401

We will go like this for our longest carbon chain; we also want to include that double bond; one, two, three, four, five.3409

Let's see, it started out as pentane; the carbonyl at carbon 1, the aldehyde makes it pentanal; the double bond makes it pentenal.3418

We have at carbon 2, we have pentene; then ?al at the ending; remember there is no number for the aldehyde.3432

This number 2 must be referring to the location of that double bond; there is nothing else for it to mean; so 2-pentenal.3441

What else do we have?--we have a methyl group at 3 so 3-methyl; 3-methyl-2-pentenal; anything else for this problem?3448

How about stereochemistry?--let's take a close look at that double bond; is there more than one way to draw this?3460

If I had this carbonyl down in this position, would that be the same molecule?--that would be a unique molecule.3467

We have to show only this stereoisomer was drawn; we have to indicate that stereochemistry as part of our name.3474

Can we use the word cis or trans here to describe this alkene's stereochemistry?--no, because we have more than two groups on the alkene; we have to use the E and Z description.3480

Remember what we do is we separate the two carbons of the alkene; our higher priority group on carbon 3, we have a methyl versus an ethyl; ethyl wins.3492

On carbon 2, we have a carbonyl versus a hydrogen; the carbonyl wins; so our higher priority groups in this case, are they on Zis same side?--nope.3504

They are on opposite sides; opposite sides means E; this is the E stereochemistry.3515

A ketone is another carbonyl containing compound; but in this case, now we have an alkyl group on both sides, a carbon group on both sides of the carbonyl.3525

That distinguishes an aldehyde which is at the end of a carbon chain because it has a hydrogen attached compared to a ketone.3535

What complicates things for the nomenclature of a ketone is you have a carbon chain and that carbonyl can be anywhere along the carbon chain.3543

We are back to the case where we find the longest carbon chain bearing the carbonyl carbon.3551

Then we number it from whichever end is closest to the carbonyl so that the ketone gets the lowest possible number.3556

What is the suffix for a ketone?--we drop the ?e ending and we add ?one; it is called an alkanone; we have to put a number out in front or in the middle to indicate where that carbonyl is.3562

Let's see some examples; the simplest ketone we can have is acetone; the common name is acetone; where does the name acetone come from?3577

Remember that acet, acetyl group we had?--the carbonyl with the CH3?--if we made that a ketone, the simplest way to make it a ketone is to add another methyl.3587

That is the ketone of the acetyl; we call it acetone; acetone, of course, very commonly used solvent in organic chemistry.3597

We use that in the lab a lot; sometimes for washing glassware, dissolving organic compounds; awesome solvent.3604

Nail polish remover, most nail polish removers are acetone based to dissolve the organic nail polish.3610

It is also very good for dissolving organic inks and permanent inks; you can use acetone; you can use your nail polish remover to dissolve paints and varnishes and all sorts of things like that.3619

So it is a great organic solvent for dissolving organic things; and it is an example of a ketone because we have a carbon chain on either side of the carbonyl.3629

What would its IUPAC name be?--we have a three carbon chain; one, two, three; it is a propane derivative; we are going to call this propanone.3638

Actually, you don't even need to put a number because there is only one propanone you can have; it must be on carbon 2.3648

But we can put that in there just to be safe; it is 2-propanone; ?o-n-e tells the world we have a carbonyl at the number given.3653

How about this next one?--where is our longest carbon chain containing the carbonyl?--let's go this way, number it from the end closest to the carbonyl.3664

We will number this way; one, two, three, four, five; this is a pentane derivative; this is called pentanone; it is going to be 2-pentanone... 2-pentanone.3676

What else does it have attached?--it has a 3-methyl and a 3-ethyl; sometimes students get confused; when they see them at the same position, they try and group them together somehow in the name.3691

But it doesn't matter if they are at the same carbon or different carbons; we list all our substituents as usual; we alphabetize them and we put them out in front.3702

Ethyl comes first; we have a 3-ethyl; methyl comes next; we have a 3-methyl; very simple; no need to panic if they are attached to the same carbon.3709

What if we have a ring here in a double bond?--how do we incorporate all this?--again, anytime we have a carbonyl in a ring, that carbon must be carbon number 1.3723

Because we are going to name it as a ketone; now we will number in this case in a clockwise direction so that the double bond also gets the lowest possible number.3731

Let's see, six carbons in a ring is called cyclohexane; with the double bond, we call it cyclohexene; with the carbonyl ketone, we call it cyclohexenone; this is cyclohexenone.3742

We have a 2-cyclohexene-1-one; 2-cyclohexene, the 2 refers to the double bond; the 1 refers to the carbonyl.3757

Of course, we can break it up completely and put the 2 right before the ?ene and the 1 right before the ?one; you will see that pretty regularly so you should be able to work with either of those.3772

Remember, we don't have to say that this is cis double bond; it has to be cis in a six-membered ring or a five-membered ring.3785

It is when we get to eight or higher that we have the possibility of having cis or trans.3792

This is another common ketone; it is nice to know the name for it; it is called benzophenone when we have a benzene ring and a phenyl group; benzophenone is the common name.3800

How about the IUPAC name?--how about the IUPAC?--we have a one carbon ketone; that is tough to do; that would be the IUPAC; this is a methanone derivative.3808

What do we have?--we have two phenyl groups; we would call this diphenylmethanone; very strange name; IUPAC names end up that way sometimes.3819

How about this last one?--what if we have two ketones?--just like we can have a diol or a diene, we are going to call this a dione.3834

Here is our longest carbon chain; we number it to give the carbonyl the lowest possible number; run into the first carbonyl; we want the lowest possible number.3845

Seven carbons is a heptane; one carbonyl would make it heptanone; this is going to be 2,4-heptanedione.3859

Just like we stuck that ?e back in there when we did a diol just so it is easier to read, we do the same thing anytime there is a di- or tri- or tetra- prefix we have to put in there.3872

So 2,4-heptanedione; what is this group attached to carbon 6 here; what are we going to call that?3882

Without the oxygen, we would just call this a phenyl group; with the oxygen, we will call it a phenoxy; at carbon 6, we have a phenoxy.3889

If we have a benzene ring, we would name the compound with benzene as the parent; let's take a look at some other aromatic compounds that we might encounter in our nomenclature problems.3904

Benzene is our... again, as I said, would be described as a parent as benzene; but there are several heteroaromatics; these are called heteroaromatic compounds.3918

That means we have aromatic rings with something other than carbon, a heteroatom--nitrogen, oxygen, sulfur, something like that.3932

These are also aromatic compounds; and these are very common names that you should be familiar with.3940

Benzene with a nitrogen replacing one of the carbons is called pyridine; this is called pyrrole, furan, and thiophene; those are real common ones that are good to know.3946

When we go to number a benzene, any of these carbons can be defined as number 1; you make that choice; but in a heteroaromatic, the heteroatom is defined as position number 1.3955

This would be 1; then you number in whatever direction you want; one, two, three, four, five, six.3967

A 2-methylpyridine means that the methyl group is attached on the carbon right next to the nitrogen; same with pyrrole oxygen; the heteroatom is always position number 1.3971

We can have some fused aromatics; it is called fused when some aromatic rings share sides; this guy is called quinoline, for example; two benzene rings attached to another is called naphthalene.3984

Naphthalene is used for moth repellants; moth balls have the same kind of smell that naphthalene does; very aromatic actually; which is where the name came from.3998

Anthracene, when you have three together, and so on; there is lots of them; just showing a few examples here; but when you have a fused aromatic, let me show you the numbering.4010

We start with one of the carbons next to the point of fusion; then we go around one ring--one, two, three, four; then we jump to the next ring--five, six, seven, eight.4019

We do not number... we skip the numbers for these because those carbons already have four bonds to carbon; there is no way you can add a substituent to those positions.4028

That is interesting; a 1,5-dimethylnaphthalene means that we have them in this position and this position.4039

When we have two benzene rings directly attached to each other, that is called a biphenyl; that is a common name--is biphenyl.4048

You may have heard of PCBs; that stands for polychlorinated biphenyls; these were used as insecticides and such.4056

They have all sorts of long lasting environmental impact so those have all been phased out; so PCBs are an important chemical that we are trying to mitigate in the environment.4068

How about the IUPAC for a biphenyl?--what would you call that?--one of these benzene rings would have to be the parent; you just pick one; that is our parent so this is a benzene derivative.4080

That is our parent; what does that benzene have attached to it?--it has a phenyl group; phenylbenzene would be the IUPAC name; phenylbenzene is another way to say biphenyl.4092

It is also nice to be familiar with these names of aromatic compounds because a lot of times the common names for other compounds are derived from the aromatic name.4108

For example, this molecule looks a lot like furan; it has the same skeleton as furan except we've gotten rid of both of these double bonds.4120

So this molecule is described... it has a common name; it is called tetrahydrofuran; because it is the same thing as furan, but we have added four hydrogens to it.4129

This is called tetrahydrofuran; it is abbreviated THF for short; that is a very common solvent that is used in organic chemistry.4140

If you have substituents on the benzene ring, we can number the ring just as usual--one, two, three, four, five, six, and describe it that way.4150

But if you have just two groups on a benzene ring, there is only three possible arrangements for those two groups; so we have common names to describe those possible relationships.4157

If we have two groups that are 1,2 to each other, meaning they are on adjacent positions, we describe that as being ortho di-substituted.4167

We either can put the word ortho in italics out in front or we could just use the letter o- will represent ortho; that describes where the two groups are attached.4176

When they are 1,3, meaning they skip over one carbon, we call that the meta arrangement; when they are 1,4, they are opposite to each other, they are called para.4186

Those are the only three possibilities; if I move the substituent over here now to the other side, this is meta again; and if I move if up here, it is ortho again.4195

So ortho and meta and para are the only three possibilities.4203

When we start getting into aromatic chemistry and learning about the reactions of benzene and benzene derivatives, we are going to be using the terms ortho, meta, para again and again.4205

You are going to eventually become very familiar with these; they can be used to very easily name aromatic compounds if we could do some common names.4217

For example, we have a bromo and iodo here; they are 1,3 to each other; they are meta; we could just describe this as meta-bromoiodobenzene.4226

Benzene is the parent; I have a bromine and an iodine; they are meta to one another; it is a flat molecule; it doesn't matter where you put the bromine, where you put the iodine.4239

As long as you put them 1,3 to each other, you are going to end up with the same compound every time; so it is really easy nomenclature.4248

If you want to number it and do it that way, now you have to be concerned with who gets carbon 1 and so on; for this, we are going to do it just like we did for cycloalkane.4253

We are going to pick the one, the substituent with the lowest... that comes first alphabetically, and we will give that to be carbon 1.4264

The bromo comes first; he would be carbon 1; then we number to give the iodine also the lowest number; we would call this 1-bromo-3-iodobenzene; it is a lot more complicated than just calling it meta.4271

We call it benzoic acid; we will see this... we will talk about carboxylic acids in a moment, on how to name those; but he is called benzoic acid; so this could be called ortho-hydroxybenzoic acid.4290

Ortho describe the relationship; so ortho, meta, and para are good to do that; or you could call it 2-hydroxy as another possibility instead of ortho.4309

But then when you have more than two groups, you can't use the words ortho, meta, and para anymore because those words have no meaning.4324

Here you could say that the two methyl groups are meta to one another; you could still use it as an adjective to describe the relationship of two groups.4332

But this molecule can no longer be described as an ortho, meta, or para molecule because there is more than two groups.4340

In this case, we are going to go back to our nomenclature rules where we find whoever comes first alphabetically, gets the lowest number.4346

We have an ethyl versus a methyl; this is number 1; then we number either clockwise or counterclockwise depending on which will give the lowest number to the next substituent.4353

We will number this way; one, two, three, four, five, six; our parent is benzene; our parent is benzene and what substituents do we have?4364

We have a 1-ethyl; how do we handle our 2-methyl and our 4-methyl?--we group them together and we call it 2,4-dimethyl; so naming a benzene is pretty straightforward.4374

There is never any stereochemistry to worry about because it is a planar molecule; every carbon can only have one substituent on there so that simplifies things.4389

But when we get into the heteroaromatic compounds, then that nomenclature can expand our vocabulary a little bit.4399

There is also a lot of common names that exist for simple compounds and simple mono-substituted benzenes; these are very useful to be familiar with.4410

In fact, you may even be required to learn them; that is quite likely.4422

For example, methylbenzene, when we just have a methyl group on a benzene ring, that is known as toluene.4426

Toluene is a very nice solvent that we use for organic chemistry; it is preferred over benzene because it is not carcinogenic; so that has some uses as well in the lab; that is called toluene.4432

It is called phenol when you have an OH on a benzene ring; it is a very special type of alcohol when you have an OH attached to a benzene ring; it is called phenol.4447

Notice the ?ol ending is just like we have for an alcohol; but it is not called benzol; it is called phenol.4457

I see I have a little typo here, sorry... this is called anisole; we will copy and paste here... it is called anisole when we have a methoxy group here instead of a methyl; it is called anisole.4465

When we have a nitrogen, this is called aniline; when we have two methyl groups, those compounds are known as xylenes.4477

Notice that this bond is pointing to the middle of the ring; that is because there is three possible places to put that second methyl; we could put it ortho or meta or para to the first methyl.4486

So there is three isomers of xylene that exist; ortho-xylene, meta-xylene, and para-xylene; together we call these the xylenes if maybe you had a mixture of those dimethyl benzenes.4498

Finally, it is called a cresol when you have an OH and a methyl; so some of these very simply substituted benzene rings have common names.4511

You are guaranteed to encounter them so being familiar with them is really going to pay off.4521

For example, this one has a methyl and an OH; they are para to each other; so this molecule can be called para-cresol.4527

Or it could be called para-methylphenol; para- or maybe 4-methylphenol; or it could even be called hydroxymethylbenzene; all sort of names you can come up with for aromatic compounds.4536

A lot of times, we get to a situation where there are more than one acceptable names; you definitely want to check with your instructor to see what their expectations are.4555

This is an interesting aromatic compound; it is a toluene derivative; see the word toluene in here?--it is called trinitrotoluene; here is the toluene; that means methylbenzene.4565

It is a derivative of that because it has these four nitro groups on it; guess what this is called?--trinitrotoluene; this is called TNT.4576

So this is the structure of dynamite; that name, when you explore that name, it comes from the common name of this aromatic derivative; very explosive.4585

Let's take a look at carboxylic acid; this is another carbonyl containing compound; a carboxylic acid has this formula here.4597

We have a carbonyl and an OH group attached; this is no longer now an alcohol; it is no longer a ketone or an aldehyde.4607

This arrangement of atoms is combined together, taken as one, as one functional group, called a carboxylic acid; it will be named as a carboxylic acid.4618

It must be at the end of a carbon chain because it has a... the oxygen stops the carbon chain; once again, like the aldehyde, the carboxylic acid defines the beginning of the carbon chain.4629

We number from that point onward to decide how long our parent chain is; but we never have to designate that the carboxylic acid group is a carbon 1 because that is the definition; it must be.4642

What we are going to do is we are going to drop the ?e ending of our alkane, and we are going to add two words; we are going to make the first word ?oic as our suffix.4655

Then we are going to do a space and then the word acid; so we are going to have an alkanoic acid; that tells us we have a carboxylic acid.4663

Again, a few common names here; our simplest acid with just one carbon is known as formic acid; this has a real interesting history for this name.4672

This is the acid that can be extracted and isolated from ants; if you take some ants and smash them up and extract the organic or acidic component, you will be able to isolate formic acid.4682

The Latin word for ant is formica; this was called formic acid since it is the acid derived from ants.4694

Again, very commonly called, typically called formic acid; but its IUPAC would be derived from the fact that it is just one carbon; it is a methane derivative.4704

But instead, we call it... we drop the ?e ending of methane and we add the suffix ?oic; then we make a space; then we put the word acid; so this is called methanoic acid.4714

Methanoic acid means I have a one carbon carboxylic acid; I have one carbon and, on that carbon, I put a carbonyl and an OH; that is what makes it a carboxylic acid.4728

This guy is called acetic acid; why do we call it acetic acid?--there is our acetyl group, our carbonyl with a CH3; when we make it a carboxylic acid, we will call that acetic acid.4739

Acetic acid is actually the acidic component of vinegar; that is what makes vinegar smell and taste that characteristic smell; it has that bite, that acidic bite.4749

Most often, we call it acetic acid; we abbreviate it AcOH by the way; a lot of times you will see that abbreviation, the Ac group, representing the carbonyl with the CH3.4762

What would its IUPAC name be?--what is its IUPAC name?--here we have a one, two carbon chain; it is an ethane derivative; we are going to call this ethanoic acid; two words, ethanoic acid.4773

How about a more complex carboxylic acid; here is our parent; we have to start at the carbon bearing the carbonyl.4788

Both of these functional groups... both of those atoms are going to be incorporated into our parent name; one, two, three, four, five; five carbon carboxylic acid is called pentanoic acid.4797

I do not need to say 1-pentanoic acid; there is no such thing; it has to be at carbon 1; what else do I have on carbon 4?4812

Now we take our substituents, we alphabetize them, we put them out in front as usual; we have a 4-methylpentanoic acid.4819

Benzoic acid is what we call the carboxylic acid with a benzene ring attached to it; benzoic acid; that is good to know.4829

We also need to know, now that we have learned about carboxylic acids... remember the priority of functional groups depends on oxidation state.4837

A carboxylic acid is the most oxidized we can have for a chain; so that is going to be our highest priority.4845

That means we are going to have to find a name for any other carbonyl that is in the structure; an alcohol group is also going to be named as a hydroxy.4855

In this example, we have three functional groups; we have an alcohol and we have the ketone and we have a carboxylic acid; all three of those functional groups exist.4865

Which is the one that is going to define the IUPAC name?--the highest priority is the carboxylic acid.4873

This is our parent chain; we are going to number to give the carboxylic acid carbon 1; so this actually incorporates the carboxylic acid; if you want to circle that, that is even more clear.4881

This is butanoic acid; no numbering there to put in our name; this is butanoic acid; we know that the alcohol group is the... the OH group is going to be called hydroxy.4894

What is a carbonyl going to be called?--it is not a keto group anymore... because it is not a ketone anymore; it is going to be called an oxo group; oxo means you have a carbonyl; not oxy; oxo.4907

Who comes first?--hydroxy comes first; we will list that first; 4-hydroxy-3-oxo-; and this is all one word, 3-oxo-butanoic acid.4919

Oxo is what we will call a carbonyl; hydroxy is what we call an OH; both of those are lower priority than the carboxylic acid.4932

Remember you can only pick one suffix; every other group then becomes named as a substituent listed out in front.4940

Now that we know how to name a carboxylic acid, let's take a look at some related functional groups.4950

These are called carboxylic acid derivatives because they can all be derived from a carboxylic acid; they are all related to a carboxylic acid.4954

We can have a... what we are doing is we are varying the group attached to the carbonyl; a carboxylic acid had an OH; and we are varying the group.4963

What all these have in common is that each of these groups has lone pairs; a halogen, remember X represents a halide.4975

A halogen has three lone pairs; oxygen has two; oxygen has two; nitrogen has one; you can see that the general structure for these carboxylic acid derivatives looks like this.4984

It has something attached to the carbonyl with a lone pair; we are going to describe this as a leaving group; this is actually going to define the reactivity of carboxylic acid derivatives.4996

We are going to see that being involved in reaction mechanisms as a leaving group; we will get to that down the road.5009

The nitrile doesn't look a lot like a carboxylic acid; but it is related just like this.5016

All of these have a carbon with three bonds to heteroatoms--an oxygen, and an oxygen, and something else with a lone pair.5023

This also has three bonds to a heteroatom, three bonds to nitrogen; so even though he looks a little different, he is also related; this is called a nitrile.5030

It is called an amide when you have a nitrogen attached to the carbonyl; it is called an ester when you have an OR group; so it is no longer an ether.5040

An ether means I have R... alkyl, and then an oxygen, and then an alkyl; that makes it an ether; when one of those groups is a carbonyl, we call it an ester.5048

When both groups on either side of the oxygen are carbonyls, we call that an anhydride; if we have a halogen attached to the carbonyl, we call it an acid halide.5058

One by one, we will go through the nomenclature for these; but I just wanted to put it in context, showing you that each of these is related to the parent carboxylic acid.5067

Because if you know how to name the parent carboxylic acid to which these are all related, then it is going to be a little easier to name the particular derivative we are looking at.5078

We will start with an acid halide; what we will do is we will find the longest carbon chain that starts at the carbonyl carbon.5090

We have to start at the carbonyl carbon; it is always carbon number 1; so we don't even mention that, just like a carboxylic acid.5097

What we do is we drop the ?e and we add the letters ?oyl; we are going to get an alkanoyl halide; then we are going to list the halide, making it an acid halide.5104

For example, again coming back to our common names, a common name for this molecule would just be called acetyl chloride; this is the acid chloride derived from acetic acid; we call that acetyl chloride.5118

What would its IUAPC name be?--we have a two carbon chain; one, two; it is an ethane derivative; but we are going to drop the ?e and add ?oyl; ethanoyl.5131

We make a space; this is another two word name; and we list whatever halogen happens to be here; it is most often chlorides that we deal with.5144

You will see that nine times out of ten; but it is possible to have other halides as well; this is called ethanoyl chloride.5151

Again, pay very close attention to these details; if you drop the -o, that name doesn't exist.5157

If you drop the -y, then you are talking about an alcohol and you've made a mistake; so be very careful; -o-y-l as our ending for an acid chloride; ethanoyl chloride.5163

How about this one?--what is our longest carbon chain?--we can include the acid chloride if you want; there is our longest carbon chain.5174

Be very careful, when you have a cyclic substituent, that you don't include the carbon of the ring as part of your carbon chain; you can't count it for both.5183

Here it is the group that is attached to the carbon chain; this is a one, two, three, four carbon chain.5192

What is a four carbon acid chloride called?--it is called butanoyl; butanoyl, space, chloride; butanoyl chloride.5201

What is attached to carbon 4?--it would be called cyclopropane if that was the parent; but as a substituent, we call it a cyclopropyl group; cyclopropyl; 4-cyclopropyl... 4-cyclopropylbutanoyl chloride.5213

How about this one?--what is our parent carboxylic acid we have?--if this were a carboxylic acid, if this were an OH, we would call that benzoic acid.5235

We are going to call this benzoyl bromide; that is our parent; kind of related to benzoic acid; we call it benzoyl bromide.5246

What do we have attached?--we have another bromo substituent; it is in the meta relationship; we could just call this meta... I'm sorry, 3-bromobenzoyl.5262

Or we could call this meta-bromobenzoyl bromide; those would both be good names for this compound.5275

Benzoyl bromide means I have something that looks like benzoic acid--a benzene with a carboxylic acid; but it is a bromine there instead of an OH.5281

An anhydride name is also very closely related to the parent acid to which it is related; let's just take a look at the structure of the anhydride.5293

If you think of the anhydride structure, it kind of looks like we have two acid pieces that have come together.5302

If you think of these two acids, what would they have to lose to result in the structure shown?--it looks like we've lost the OH on one and the H on the other; so we lost H2O.5306

If we lose H2O, these two carboxylic acid groups can come together and form the structure, the product, shown; that is why it is called an anhydride--you've lost water.5323

In the simplest case, where these two alkyl groups are the same, then we simply name it as the parent acid; but instead of calling it an alkanoic acid, we call it an alkanoic anhydride.5336

For example, this came from acetic acid; this is related to acetic acid; we could call it just acetic anhydride as its common name; this is acetic anhydride.5347

The abbreviation for that is Ac2O; it has two Ac groups, acetyl groups, attached to the middle oxygen; but what is its IUPAC name?5362

For the IUPAC name, let's take a look at just one half and name that acid; that acid would be a two carbon acid; it is an ethane derivative; this would be ethanoic acid.5372

Ethanoic acid, so now we call this ethanoic anhydride; we just replace the word acid with anhydride.5385

What if it is not a symmetrical anhydride?--we call those mixed anhydrides, meaning it came from two different acids if you will; then all we do is list both acid groups before the word.5395

What carboxylic acid did this come from?--one, two, three; this was a propanoic acid; and over here, this came from one, two, three, four; this came from butanoic acid.5408

When we brought those two acids together, if we think about that as a way to come up with the IUPAC name, we just list them alphabetically; this is butanoic propanoic anhydride.5424

That is so simple; it seems like that would be a common name but that is actually how you do the IUPAC name; you just list the two halves to the anhydride.5442

If you had a diacid like this... again, there are common names associated with most of these diacids; oxalic, molaic, succinic, glutamic, and so on.5451

These are... you might come across these common names; it is going to be useful in this case; this is called succinic acid.5465

Let's try and do the IUPAC for this one just to see if we could do that; it is a four carbon chain; one, two, three, four; one, two, three, four; it is a butane derivative.5472

If we had just one carboxylic acid, we would call it butanoic acid; because we have two, we call this butanedioic acid.5484

Remember we add that -e back in so we can fit the d-; butanedioic acid; remember ?oic acid is our suffix; just like we would have diol or dione, we could have dioic acid.5498

If we take succinic acid and lose water from this structure, what can happen is the two carboxylic acid groups can come together to form a cyclic anhydride.5512

In fact, we are going to be seeing the mechanism of this eventually; what we will get is a five atom ring that looks like this.5522

That is an anhydride structure; you have the oxygen with a carbonyl on both sides; this is definitely anhydride.5532

The way we describe this anhydride is by referring to the parent acid it came from; this is called succinic anhydride; succinic anhydride.5539

Believe me, you don't want to know the IUPAC name for this; this is really how most of us refer to it--is just by its common name.5554

Some of these cyclic anhydrides you will see are named... their name comes from the common name of the parent diacid.5561

I think esters are a little tricky to name because an ester has two R groups; it has the R group that is attached to the carbonyl side; and it has the R group that is attached to the oxygen side.5572

It is possible to mix those up when you are first learning; but let's see how we can keep them straight.5587

I think the way to do that is to immediately take a look at an ester structure and immediately break it down to--here is the parent acid to which this ester is related.5594

This looks like the carboxylic acid group; this is the parent chain; this is the parent right here; and this is just an additional alkyl group that added on to make it an ester rather than a carboxylic acid.5605

What we are going to do is we are going to drop the suffix ?oic acid and instead we are going to use the suffix ?oate to tell everyone that it is an ester instead.5621

What we are going to do then is we are going to list in front, we are going to list the alkyl group that makes it an ester.5632

Ultimately, our name is going to be an alkyl, space, alkanoate; the alkyl group is this part that is attached to the oxygen; the alkanoate is our parent just like the alkanoic acid was.5640

A lot of words; let's just look at some examples and I think it will make a lot more sense.5653

For example, this is acetic acid; we call that acetic acid; its IUPAC is ethanoic acid; ethanoic acid is related to this ester because we still have the components of ethanoic acid.5658

We still have the two carbons and the carbonyl with the oxygen attached; but it is now an ester because there is an R group here; there is an alkyl group instead of a hydrogen.5675

Instead of calling it ethanoic acid, we are going to call it ethanoate; we are going to use the suffix ?oate to indicate that it is an ester.5686

There are a lot of ethanoate esters you can have; all sorts of different esters you can have because this alkyl group can vary.5697

Which ester do we have in this case?--we have the methyl ester; we just list the word methyl out in front; this is methyl ethanoate.5704

Its common name for an ester would be acetate, for this acetyl group as an ester; we would call this methyl acetate; that is a very good common name to know as well.5715

Let's try another example; this is an ester because we have a carbonyl with an OR group attached.5726

How do we name it?--first we really want to identify the parent acid; here is the carboxylic acid that is related to the ester of which it is a derivative.5735

How would you name that acid?-it is a three carbon acid; one, two, three; it is a propane derivative; you would call it propanoic acid.5747

We are going to name this propane ester, we are going to call it propanoate; we are going to call it propanoate; drop the -e and add ?oate; so it is propanoate.5757

Which ester is it?--what do we have over here?--this is an ethyl group making it an ester; we call this ethyl, space, propanoate; esters are named as two words; ethyl propanoate.5770

Let's try another one; this one is a little more complex; here is our parent ester, a parent chain because that came from the carboxylic acid.5786

Remember the carboxylic acid is the highest priority functional group; that must be our parent; we are going to number from there; one, two, three, four, five.5800

It is pentane that we started with originally; but we have a double bond here; so this is actually going to be called 4-pentene... 4-pentene.5811

But it is not pentene; it is an ester; what suffix do we use for an ester?--we drop the ?e and we add ?oate; this is called 4-pentenoate.5823

Remember double bonds and triple bonds, we can always sneak into our name because they affect a different part of the parent name.5836

They just replace this -a with a -e or a ?y; so we can always incorporate those in there.5844

4-pentenoate; the 4 must be referring to the double bond because the ester needs no number; the ester must be on carbon 1; this is good so far.5849

Now we ask what is the alkyl group that is making it an ester?--we come over here; this is a little complicated now.5859

This is a complicated group; we just have to recall that the carbon point of attachment is defined as carbon 1.5868

What is our longest carbon chain?--that is it; it stops right there; this is a methyl group... this is a methyl group.5878

But it is not just methyl; what does it have attached to it?--it has a phenyl group attached to it; we are going to call this phenylmethyl; phenylmethyl, space, 4-pentenoate.5884

Phenyl methyl, I just realized was on the previous slide; I forgot to mention that with the aromatic nomenclature.5900

This group, there is a common name for a benzene ring with an extra carbon; it is called a benzyl group.5908

The carbon next to a benzene ring is described as a benzylic position; this is called a benzyl group.5917

A common name for this might be benzyl 4-pentenoate; that would be the common name; but the IUPAC name is phenylmethyl, space, 4-penteneoate.5922

Once we figure out how to name esters, it turns out we can use that same nomenclature to describe carboxylate salt; it is called a carboxylate when you have an RCO2-.5932

RCO2-; it is like a carboxylic acid that has a lost a proton; it has been deprotonated; we call that a carboxylate; we use the exact same rules to name this.5945

Again, we look at the parent acid from which it is derived; this would benzoic acid; now we call it a benzoate with the negative charge there; this is called benzoate.5958

In this case, it is not an alkyl group that is making it the benzoate; it is a sodium; we just list the counter ion in front; sodium benzoate.5974

So you could have sodium acetate; you could have... you could have lithium pentenoate here if this was the lithium salt.5983

You will come across those names as well when you are looking at carboxylate salts; so that is good to be familiar with that nomenclature.5995

Amide nomenclature goes as follows; an amide is when you have a carbonly with a nitrogen attached.6005

It is no longer an amine; that carbonyl now makes it an amide; again all the difference that a single letter makes.6013

Once again, this must be carbon 1; we count the carbons from that point forward, find the longest carbon starting from there.6020

What we for our name is we drop the ?e and we add the entire word -amide; so we get an alkanamide as the parent; the suffix is the entire word ?amide.6028

If we have groups attached to the nitrogen, as usual just like we did for the amines, we will identify those as N-substituent.6040

Again let's look at the very simplest example; acetamide is what we call it when we have the acetyl group that is turned into an amide.6049

What would its IUPAC be?--we just have a two carbon chain; that is an ethane derivative; this is an ethane derivative.6058

We drop the ?e of ethane and we add the word ?amide; ethanamide; ethanamide would be the name of this compound.6066

This guy is called N,N-dimethylformamide; let's see if that name makes sense to us; where does formamide come from?--it comes from formic acid.6077

Formic acid was our simplest carboxylic acid; that is the one that came from ants; like formaldehyde.6087

That is where the name formaldehyde comes from--is related to formic acid; that is the aldehyde with this one carbon structure.6096

This is the one carbon amide; we call that formamide; it is N,N-dimethyl because there is two methyls on the nitrogen; that is N,N-dimethyl.6103

Formamide is its common name; that is a good one to know because it is abbreviated DMF; this is a solvent that is used in organic chemistry; so you might see the abbreviation DMF occasionally.6112

How would this name change if we wanted to do IUPAC?--because formamide is not an IUPAC name; what would the IUPAC name be?6125

This is just a one carbon chain; that means it is a methane derivative; we would just call it methanamide; we drop the ?e of methane and add -amide.6134

It would still be the same beginning; it would still be N,N-dimethyl; but it would be N,N-dimethylmethanamide rather than N,N-dimethylformamide.6145

Let's try an example here; we have a lot going on; let's identify the highest priority functional group and let that set which one will be our carbon chain, our parent chain.6156

Right here, this is the carbon that is most important because that has the carbonyl and the nitrogen; that is going to be our parent chain.6170

This is the longest carbon chain from that point on... from that point on; this is one carbon, two, three, four; this is a four carbon chain.6177

What is that going to be called?--it looks like a butanamide; butane derivative; now butanamide; butanamide means that I have an amide at carbon 1; carbonyl plus a nitrogen.6188

What else do we have here?--we have an N-ethyl; a lot of times the N substituent is listed all the way out in front of the molecule before the carbon substituents are sometimes mixed in.6203

It maybe depends on the publisher; this is called an N-ethyl because it is an ethyl group on the nitrogen.6216

What is this group called?--what is that group called?--if you could use common names, there would be a simple name for this; it looks like the isopropyl group with an oxygen.6224

We could call this an isopropoxy; we could call it an isopropoxy but that is not IUPAC; let's figure out an IUPAC name for this substituent.6235

Remember the point of attachment has to be carbon 1; this is a two carbon chain; this is actually an ethyl group.6248

But it has a methyl at carbon 1; it is a 1-methylethyl is how we would call an isopropyl group; but it also has the oxygen here; we are going to call this 1-methylethoxy.6257

It is actually an ethoxy group; here is the ethoxy; but it is a derivative of that because, at the 1 carbon, it has an extra methyl; this is called a 1-methylethoxy.6274

Like I said, usually the end substituent come first; it turns out that is also alphabetically correct; so we are in luck here.6286

This is N... I'm sorry, N-ethyl is listed first; then at position 2, we have this big whole group; -2- and then parentheses to keep it all together; a 1-methylethoxy.6295

Our nomenclature rules are building on one another bit by bit so that we can eventually name some pretty complex molecules.6313

Finally let's take a look at a nitrile; a nitrile is RCN; so we have that C-N triple bond group; that is also a carboxylic acid derivative.6323

It also indicates that the first carbon, the carbon of the nitrile, defines the beginning of the carbon chain; just like the carboxylic acid derivatives.6336

I typically don't bother trying to distinguish who has a higher priority among the carboxylic acid derivatives.6346

Assuming you have just one of those, that is going to be higher priority than any other functional group we saw.6353

But if you want to get into the details of how do they rank amongst each other, you can look that up and have those challenging problems.6359

We are going to find our longest carbon chain; then we are going to not even drop the ?e of our alkane name; we are just going to add the word nitrile.6367

That must be the simplest suffix to remember because you don't even have to drop the ?e; you just stick the word nitrile on the end; that magically turns your carbon chain into a nitrile instead.6377

This is a tricky one to recognize; this molecule's common name is acetonitrile; but you can see that it is the two... just like... remember this was the acetyl group.6391

It is the two carbon derivative that we had all these names for--acetone, acetic anhydride, acetic acid, acetamide, etc; the two carbon nitrile is called acetonitrile.6402

Again, even though it looks quite different from the others, this is a common name; another very common solvent to use in organic chemistry; so you might see acetonitrile around.6415

But what would the IUPAC name be for acetonitrile?--our longest carbon chain is right here; it is just a two carbon chain; that is an ethane derivative; he is called ethanenitrile.6423

That is it; you just add the word nitrile to the end; ethanenitrile; notice that the cyano group is part of the carbon chain; it is part of the carbon chain; that is important here.6435

You might at first glance, at the way this is drawn, you might think that your parent is down here and then you have some kind of cyano group attached.6445

It would be called a cyano group if we had some higher priority functional group here; but we don't; the cyano group is the highest priority functional group.6453

So that is actually part of our parent; our carbon chain has to start right here; from that point, our longest carbon chain goes in either direction because it is symmetrical.6460

But this must be our parent; one, two, three, four, five; this is actually a pentane derivative; we are going to call that pentanenitrile... we are going to call that pentanenitrile.6470

What do we have attached?--we have some methyl groups; and then we have another one of these complex substituents; let's see if we can tackle that; how do we start?6488

We look at the point of attachment to the parent; we define that as carbon number 1; then we number from there; what is the longest carbon chain starting from that point?6496

The longest carbon chain would be one, two, three; it doesn't matter if you number up here or down here; one, two, three; this is actually a propyl group.6506

It is a propyl group; but that does not... it is not just a propyl group; it has a methyl at carbon 1 and a methyl at carbon 2.6514

What are we going to call this?--we are going to call this a 1,2-dimethylpropyl; it is a 1,2-dimethylpropyl.6524

We are going to put that whole big thing in parentheses because it is all one group that is attached to the parent; it is attached to the parent at carbon 2; it is called a 1,2-dimethylpropyl.6537

I listed that last... I listed that second because the other groups we have are methyl groups and methyl comes before methylpropyl.6551

Remember we ignore the di- for alphabetizing; but methyl comes before methylpropyl because methylpropyl is all one word.6559

At 3, we have a methyl; at 4, we have a methyl; we are going to call that a 3,4-dimethyl.6565

Make sure you give yourself plenty of room when you are doing these nomenclature problems because the names can get really big and long.6572

Make sure you draw your letters nice and large and clearly so that there is no mistaking an ?e for an ?a or ?o because, as you can see, that makes all the difference in getting these problems correct.6578

Let's do this last one; this looks like a doozy doesn't it?--we have an aldehyde; we have a ketone; we have an alkene; we have a nitrile; which of these groups wins?6591

Remember it is based on the oxidation number; any carbon with three bonds, two oxygen, or two heteroatoms is going to win; so this is our highest priority functional group.6604

He will be named as a nitrile; all the other groups are just substituents attached to the parent because we can only have one suffix.6615

Let's include that nitrogen in our parent so we make sure that we have already accounted for it; one, two, three, four, five, six, seven; seven carbon chain is heptane.6624

Double bond makes it heptene; we have a 2-heptene... 2-heptene; how do we make this a nitrile?--we just add the word ?nitrile to the end.6643

That means the first carbon of that seven carbon chain is part of a carbon-nitrogen triple bond; we have 2-heptenenitrile.6659

What do we have at carbon 4?--remember we would name it as a ketone if that was the highest priority functional group; then we would use the ?one suffix.6667

But now it is a substituent; he is not called a keto group; that is a really common mistake; instead he is called an oxo group; any carbonyl is called an oxo substituent.6679

We have an oxo at 4 and we have an oxo at 7; again now an aldehyde or a ketone, they are both the same thing, they are just carbonyl substituents.6689

We are going to call this a 4,7-dioxo; just like we would have a dimethyl or a dichloro or a diphenyl; this is called a dioxo; excellent.6700

That accounts for all our functional groups; but there is one last thing that is missing here; is there any stereochemistry that might be relevant?6717

Look at this double bond; how would you describe that stereochemistry?--both of these groups are pointing in the same direction, on the same side.6724

So yes, actually the cis isomer has been shown here; we need to show that; it is okay to just call it cis here because you have only two groups.6731

It is also okay to call it Z; it is never wrong to use the E and E nomenclature; if you want to get used to doing that, then that is a good idea.6739

Z means these two groups are on Zis same side; in fact, in some cases, sometimes you will learn that unless you have two identical groups, they prefer not to use cis but to use Z instead.6750

But if you have two hydrogens, it is quite unambiguous if you call it cis; that is why they accept it as an okay name as well.6763

That wraps it up for all the different functional groups that we are going to learn the nomenclature for; I realize nomenclature is not the most fascinating topic in the world.6774

But just like you have to memorize the alphabet before you can learn how to spell and learn how to put words together, you do need to memorize these nomenclature rules.6782

It is one of the few things in organic chemistry that really you do have to memorize; you do have to know the names; because we need to be able to communicate.6791

If every time you see one of these IUPAC names, it is a huge roadblock for you when you are going to have to spend ten minutes figuring out what it means; that is going to be very costly.6799

So it is worth to maybe put together some flashcards and start to get familiar with these; of course, the more problems you work on, the better you are going to get.6808

And the more it is going to be second nature to you just like the alphabet is now that you have had plenty of time to practice that.6817

Hope to see you again soon; thanks for coming.6824