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Dr. Laurie Starkey

Dr. Laurie Starkey

Infrared Spectroscopy, Part II

Slide Duration:

Table of Contents

I. 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
II. 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
III. 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
IV. 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
V. 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
VI. 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
VII. 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
VIII. 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
IX. 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
X. 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
XI. 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
XII. 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
XII. 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
XIII. 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
XIV. 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 (27)

1 answer

Last reply by: Professor Starkey
Thu Oct 6, 2016 1:07 PM

Post by Tane Boghozian on October 4, 2016

Hi Dr. Starkey, I have been using educator. com for almost four months and its great!
Thank you very much for the great lectures. I have learned a lot. I have a question about your availability. Would be possible to talk to you about my experiments and research whenever I have questions? will you answer my questions?
Thanks a lot for your help.

1 answer

Last reply by: Professor Starkey
Thu Aug 13, 2015 9:59 AM

Post by sandi imayeguahi on August 13, 2015

That was your best lecture by far. Your really great.

1 answer

Last reply by: Professor Starkey
Sun Apr 26, 2015 9:49 PM

Post by Nagasrinivas Tripuraneni on April 26, 2015

Professor, thank you for the informative lecture.

1 answer

Last reply by: Professor Starkey
Fri Oct 18, 2013 2:10 PM

Post by brandon oneal on October 18, 2013

The only question I have is how can you tell which compound it is?

1 answer

Last reply by: Professor Starkey
Sun Jul 21, 2013 10:44 PM

Post by Parabjit Kaur on July 21, 2013

when will you post lectures on the mass spectrometry ?

1 answer

Last reply by: Professor Starkey
Thu May 9, 2013 10:19 AM

Post by Nawaphan Jedjomnongkit on May 6, 2013

If we have internal and symmetrical alkyne, can we differentiate from normal alkane? Because what we can get from IR spectrum is only SP3 CH no SP CH and CC triple bond.

1 answer

Last reply by: Professor Starkey
Sun Feb 3, 2013 11:03 PM

Post by Ramin Sadat on February 3, 2013

Will you be posting anything on Mass spectrometry ?

1 answer

Last reply by: Professor Starkey
Tue Jan 29, 2013 9:47 PM

Post by Edi William Yapi on January 29, 2013

Good Lord.... You are just a great instructor !

1 answer

Last reply by: Professor Starkey
Sun Jan 13, 2013 11:54 AM

Post by Janaki Dharmarpandi on January 12, 2013

you are awesome!!!!

1 answer

Last reply by: Professor Starkey
Sun Dec 2, 2012 11:43 AM

Post by ali aden on December 1, 2012

you are amazing, i did understand this material, excepts i have a little confussion o the finger print area.

1 answer

Last reply by: Professor Starkey
Mon Aug 13, 2012 9:05 PM

Post by Daniel Ugsang on August 10, 2012

Honestly, you are a LIFE SAVER. My O-chem prof is good but goes off on tangents. You get right to the point. Succinct. Good explanations. I really hope I pass Ochem and if I do, it'll be because of you, Professor Starkey!

1 answer

Last reply by: Professor Starkey
Tue Jul 17, 2012 9:55 AM

Post by nouf alkusayer on July 7, 2012

U r amazing !!!!

1 answer

Last reply by: Professor Starkey
Fri Feb 3, 2012 11:33 PM

Post by Lukasz Skora on February 3, 2012

Hi Dr. Starkey, awesome lectures! They are life savers!. I have a question, does it depend on the finger print region if you wanted to deduce how long the compounds is. How for example can one tell if it's a butane or a decane, or like pentanol, hexanol, or octanol. They are all sp3 CH's with an alcohol at the end. Or a benzene with a longer substituent compared to a shorter one. Thank you.

0 answers

Post by Thomas Notto on November 23, 2011

Great Job on the basics of Infrared Spectroscopy... I think I got now!!!

Infrared Spectroscopy, Part II

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
  • Interpretation of IR Spectra: a Basic Approach 0:05
    • Interpretation of IR Spectra: a Basic Approach
    • Other Peaks to Look for
  • Examples 5:17
    • Example 1
    • Example 2
    • Example 3
    • Example 4
    • Example 5
    • Example 6
    • Example 7
    • Example 8
  • IR Problems Part 1 28:11
    • IR Problem 1
    • IR Problem 2
    • IR Problem 3
    • IR Problem 4
    • IR Problem 5
    • IR Problem 6
  • IR Problems Part 2 42:36
    • IR Problem 7
    • IR Problem 8
    • IR Problem 9
    • IR Problems10

Transcription: Infrared Spectroscopy, Part II

Hi, and welcome back to Educator.0000

We are going to continue the topic of IR spectroscopy next.0002

We are going to think about how to approach a spectrum if we need to interpret them.0006

What I have done is: I have written out a kind of a basic approach that is a good place to start; it's nice to have a systematic approach, so that you are not kind of floundering around and missing things.0011

If you have a systematic approach, and you do the same thing every time, you are going to be more consistently getting things right.0023

OK, so what I suggest is that you start by just reading the spectrum from right to left, like you would read a sentence.0029

The first thing you should do is look for the following obvious peaks: these are things that you should not miss, anytime they are in an IR spectrum.0036

OK, as we read from right to left, the first thing we would encounter is an OH or an NH signal; that comes somewhere around 3300.0042

Remember, that is a very broad signal; OK, we want to be careful of this, though, because a lot of times, we see an OH signal in our spectrum; we are not expecting an OH--the molecule that we are analyzing shouldn't have an OH.0050

OK, and that is because there is a very common contaminant that we might have in our sample that does have an OH, and that is water.0064

So, sometimes, if our sample is just wet (meaning we have done, let's say, an extractive workup, and we have isolated our product, but we haven't properly dried the sample), we might be taking an IR spectrum of water along with our sample.0074

And so, we will see a peak around 3,300, and we will learn to disregard that as water (or maybe a protic solvent, or something like that--an alcohol).0087

OK, but we should be able to pick out whether or not there is an OH present in the sample.0097

OK, then we are going to come right to that 3,000 cutoff, because we know that is where our CH bonds are going to appear, and we know that if they are just above 3,000--just to the left of it--that is where our sp2 CH's come from.0102

And, if they are just below, just to the right of it, that is where our sp3 CH is; so that is going to tell us whether we have maybe an aromatic or an alkene, or maybe some alkyl carbons.0120

OK, if it's aromatic or if it's alkene, we can also look for those substitution patterns--those strong peaks below 1,000.0129

They are in the fingerprint region, so it's not easy to find right away, but we might look for those later.0140

OK, and like we saw in the previous spectra that we looked at: most spectra are going to have the sp3 hybridized CH's in them, and so we are usually going to see these peaks just below 3,000.0147

So, we can kind of get used to seeing that and labeling that.0160

OK, we are going to continue reading along; we are going to look at the region around 2,200, and that is where we find our triple bonds (either a nitrile or an alkyne).0163

OK, now, these are often very weak: they are usually very, very small signals; but because that area around 2,200 is normally completely flat, if you see a peak at 2,200, that is something that you should recognize and pick out.0173

OK, and finally, around 1,700 is: we have our carbonyl; this is a very strong peak; this is very obvious; all of these peaks are things that you should never miss if they are present in your IR spectrum.0188

OK, and somewhere around 1,700 is where you say it is lowered by conjugation; we are going to expect the lower number if it's conjugated to a benzene ring or another double bond, and so on.0200

So, like I said, where exactly around 1,700 it is depends on what kind of a functional group: is it a ketone?--is it an ester?--and so on.0210

OK, now, besides those obvious bands, some things that we can look for for additional evidence are the other things we will find in our correlation tables.0219

We might have an sp hybridized CH; that is also around 3,300, but that is now a sharp peak, compared to the alcohol's OH broad peak.0228

An aldehyde CH is very small peaks, hard to find, hard to see initially; but we can look for them.0238

Remember, those are our little vampire fangs: 2,850 and 2,750; we can look for those.0245

Carbon-carbon double bonds: we may or may not find those; they are often variable intensity; sometimes they disappear altogether.0250

If it's a symmetrical, symmetrically substituted alkene, we won't see the peaks at all.0258

OK, C-O stretches: again, they are typically strong, somewhere around 1,050; but sometimes it is hard to find those, too, because they are in the fingerprint region.0264

OK, carboxylic acids are pretty unique, because that OH stretches so spread out, and we have that in combination with the carbonyl (that is something we can look for).0272

And then, if we do have an aromatic ring--a benzene ring--in our structure, then depending on the substitution pattern (so I have shown one group here, and then, kind of attached at the middle here, I have another group meeting--it could maybe be ortho or meta or para), we can look for those out-of-plane bending peaks around 1,000 and those overtone peaks at the aromatic ripple.0282

OK, and there are also characteristic patterns if it's trisubstituted and so on; I just wanted to show you some examples of that ortho, meta, and para, and the monosubstituted.0308

OK, so let's get started with our first spectrum; and what I have shown here are the 8 compounds that we have already analyzed, and predicted the peaks for, because it turns out that the spectra we are going to be looking at from this point forward actually match one of these.0318

Let's see if we can interpret the spectrum, and then find out which structure it matches.0332

Here is what we are going to do: we are going to read it from left to right, just like we would a sentence, and we are going to start and look for our obvious peaks.0339

We start, and we look: around 3,300 is where we find an alcohol, an OH: do we have an alcohol here--do we have an OH?0347

We sure do--this big, broad peak around 3,300 is exactly what an OH looks like.0354

We can point to it; we can circle it; we can do something to label it.0361

Very clearly, though, we want to get in that habit of labeling our spectra.0365

OK, then we continue reading left to right; we move to this 3,000 mark, and we look just above 3,000 for peaks; and sure enough, we see some peaks here.0371

We also see some peaks just below 3,000, so what does that tell us?--just above 3,000 is where we find sp2 CH's, and just below 3,000 is where we find sp3 CH's.0380

OK, we continue reading: we go up to 2,200; here is 2,200; we look for peaks there; do we have a triple bond?0394

There is no triple bond there; we continue to 1,700; here is 1,700--is there a carbonyl?--could that be a carbonyl--this little tiny peak--could that be a carbonyl?0401

No way--remember, a carbonyl is the biggest, strongest peak in your whole spectrum; so these are the obvious bands that you can't miss, so there is no carbonyl; there is no triple bond.0411

OK, so just based on these functional groups that we know are present, let's take a look at our structures 1 through 8 and decide which spectrum we have--which compound we have.0422

Well, we know there is an OH; and actually, there are only two choices that have OH's; how would we distinguish between 6 and 7?0432

Well, there are two ways: one of them is: 7 must have a carbonyl, and we know we don't have a carbonyl (right?--we could just kind of make that note here: no carbonyl--just for your information; I wouldn't really put that on my spectrum).0442

OK, but it can't be 7, so it must be 6; it has the OH; it has the sp2 CH; it has the sp3 CH.0454

OK, now what else can we look for?--if we know it's 6, and we are thinking that it's 6, now let's go back and find some of those needles in the haystack that will more completely label this spectrum and give us further evidence.0462

For example, because it has an aromatic ring, how would you describe that aromatic ring?0476

It is a monosubstituted ring; in fact, I see this aromatic ripple up here; that is consistent with the monosubstituted: 1, 2, 3, 4.0481

And we also look to find...we should find two peaks around 700 and 750; and there they are, so this is monosubstituted aromatic; we call this out-of-plane bending.0491

This gives us more evidence for that structure.0506

OK, is there anything else?--maybe we could look for that C-O stretch, and maybe one of these is a C-O; I'll put a little question mark here; there are two peaks here; I don't know for sure which is the C-O.0509

So, that is nice to attempt to label, but some things we are not going to be able to identify with certainty.0524

OK, also, with the benzene ring, maybe this peak around here at 1,600 is the carbon-carbon double bond; maybe we could put a little question mark there--I don't know for sure.0531

That is, we would expect to find something around that region, so that is probably a good guess.0542

OK, let's try another one.0548

We will start by reading the spectrum from left to right: the first thing we should be looking for around 3,300 is an alcohol--do we have any OH's?0552

Well, we have this tiny little blip, but that sure doesn't look like anything significant; so we have no OH here; we continue to 3,000; here is 3,000.0559

We look just above--anything just above 3,000?--that is empty, so there is no sp2 CH (we'll just put a little note up here on what we are seeing).0570

How about just below 3,000?--yes, here we have our first significant peak, so we will label those: we have sp3 CH; we continue down, reading left to right.0579

At 2,200, do we have any triple bonds?--no triple bonds.0590

And then, we move down to 1,700; at 1,700, what do we find?--oh, we do have a carbonyl.0599

OK, again, a systematic approach means we are going to be looking for our obvious peaks, and we are not going to missing them any time they show up.0606

Let's take a look at structures 1 through 8: what compound has a carbonyl, an sp3 CH, and nothing else?0613

OK, so it can't be the carboxylic acid, because it had an OH; and we actually have three compounds with carbonyls.0624

All right, so we can cross these ones off as not being possible; these ones are our three contenders--how would we distinguish between them?0632

These two are ketones--1 and 4 are ketones, and 3 is an aldehyde; and there is something else that distinguishes them--how about our CH's?0642

We said that there is no sp2 CH, but 3 has a benzene ring and 4 has a benzene ring, so those cannot be our structures.0653

So, we actually have just one possibility here: this has to be this ketone, because all we have are sp3 CH's and a carbonyl.0660

OK, is there anything else I can look for to label?--really, there is nothing else.0672

Look at all of those peaks in the fingerprint region that we are just leaving alone; OK, sometimes that is going to be frustrating--you might find that frustrating--but the key to solving IR problems is knowing which peaks are significant, being able to pick those out.0678

We have to resist the temptation to label every single squiggle and wiggle, because these are not significant peaks--it is simply your molecule bending and wobbling all around, and that doesn't really tell us anything diagnostic.0694

OK, so just those two peaks are all we need to label to positively identify its structure.0706

OK, how about our next one?--again, systematic approach: what is the first thing we should look for?0714

Reading left to right, we look at 3,300, and we see that there is no OH; we just make a little note to ourselves here, and we move to 3,000.0719

We move to 3,000, and what do we find?--anything above 3,000?--sure; we have these three peaks up here.0729

It doesn't matter if they are big or small or anything; any peaks up here are significant--right about 3,000 but just above it means we have sp2 CH.0736

It could be a benzene ring; it could be an alkene; it doesn't matter right now--all we know is: we have sp2 CH; and then just below 3,000, we have sp3 CH.0746

OK, systematic approach--what else do we look for?0757

2,200: there is no triple bond; 1,700: we look for a carbonyl--no carbonyl.0759

OK, so those are our obvious peaks; let's see if that is enough to identify the compound.0773

We need a compound without any carbonyl, without any OH; all we have are sp2 CH's and sp3 CH's.0779

So, what do you think?--it looks like compound 8 is the only structure that has no other functional group in it, that has both sp2 CH and sp3 CH.0788

That looks good; now, is there anything else I can find if I know 8 is my structure?0802

What about that benzene ring?--we would expect...oh, there it is: there is our aromatic ripple.0808

And this is a little harder to read, very often, about the substitution pattern, but we can look over here to find our substitution pattern (this is another example of a monosubstituted): here it is--750, 690--monosubstituted aromatic is the way we describe that out-of-plane bending motion.0818

OK, very good.0842

OK, let's try the next one: let's read it from left to right.0845

Do we have any OH at 3,300?--well, we have a peak at 3,300; does that look like an OH to you?--remember, an OH, because of its hydrogen bonding, is going to be a very broad signal; this is not consistent with an OH.0848

It is obviously something, but we will come back to that; we have no OH.0863

We move down to 3,000; do we have anything above 3,000?--we have something way above 3,000, but remember, we are looking immediately at 3,000.0867

There is nothing here, so there is no sp2 CH; but just below 3,000, we do have sp3 CH.0877

We continue down to 2,200; do we have anything at 2,200?--oh, we sure do, and what is it that we find at 2,200?0887

That is where we find carbon-carbon triple bonds or carbon-nitrogen triple bonds--we don't know which one it is yet.0895

They both come around 2,200; so we have a triple bond; and how about a carbonyl--any carbonyls?0901

That would be at 1,700 (remember, feel free to use your correlation table: you don't have to memorize these numbers--feel free to use that to confirm), but there is no carbonyl.0908

OK, so we look at our structures: we are lucky enough to have just a single structure that has a triple bond, but let's see if this is consistent.0921

What else would we need to have if this were our structure?0930

This hydrogen is very special--how would you describe that hydrogen?0935

It is attached to an sp hybridized carbon, so this is called an sp CH bond, and where does that stretch show up?--it shows up right around 3,300.0940

So, why is this peak so skinny--so narrow and sharp?--it is because this is an sp CH stretch, rather than an OH.0951

OK, and so, if this is a CH, that tells us we don't have a nitrile; it's not a C-N triple bond, because we need a hydrogen on a carbon; so this has a hydrogen on one side, and then the rest of this alkyl chain on the other side.0962

Now, we know exactly what we have here.0977

Anything else we can pick out from that structure?--nothing else of interest; so we'll ignore this fingerprint region and just label those three peaks.0980

OK, let's continue: let's read this left to right.0994

If you want to pause any time and try the rest of the spectrum (or spectra) on your own, that is a very good idea--a very good exercise.0997

OK, the same systematic approach: any alcohols (3,300)?--we have this tiny little blip, but that is not a nice, strong peak, so we have no OH.1004

What do we see at 3,000?--at 3,000, we have these peaks above--very tiny, but that is OK--it is still significant: sp2 CH is just above 3,000; sp3 CH is just below 3,000.1018

OK, 2,200--anything at 2,200?--it is nice and flat, as usual.1034

1,700--where is 1,700?--sometimes it is hard to read these numbers, but look: this is 1,500; this is 2,000, so this must be 1,700; use the axis labels down here to help you pick out the thing.1040

The big peak at 1,700--what does that tell you?--carbonyl, for sure.1056

So, what we need is a compound that has a carbonyl; it also has both sp2 and sp3 CH's.1062

We come back to our carbonyl compounds: there is no OH, so it can't be that one; it can't be #1--what is wrong with #1?--#1 has no sp2 hybridized carbon with a hydrogen on it.1071

It has this sp2 hybridized carbon as the carbonyl, but it has no sp2 CH.1088

OK, but 3 and 4 both fit the bill here: they both have a carbonyl; they both have an alkane-type carbon; and they both have an sp2 CH.1093

So, how would we distinguish between 3 and 4?1106

What sets them apart?1110

3 has a hydrogen attached to the carbonyl (we call that an aldehyde); 4 does not (it's a ketone).1111

How would we find the presence of an aldehyde?--we would look for our vampire fangs at 2,850 and 2,750; and they are not there.1119

OK, so there is no aldehyde; it must be the ketone.1128

We can make a little note here on how we made that decision: there is no aldehyde CH.1131

And so, that is what makes it compound 4 instead of compound 3.1139

You want to make sure that, after you have made a choice...you should go ahead and draw the structure right on the spectrum, because then there is no mistaking: every functional group that is on this structure needs to be in the spectrum and vice versa.1144

If you said you had a carbonyl, your structure has to have a carbonyl; so that is a very rewarding part about solving spectroscopy problems: you can see the evidence when you have made the right choice.1159

OK, how about our next one?--let's look for an OH; at 3,300, do we have an OH?1174

Well, not really, but we have kind of a big mess here; that looks a little interesting; we will kind of leave that for now.1180

But what do you see when we move to 3,000?--just above 3,000...1190

We could make a little question mark here; there is no obvious OH peak like we are used to seeing; so we will leave that as an unknown for now.1195

Just above 3,000, though, I see some peaks here, so there is an sp2 CH; and just below 3,000, I have sp3 CH.1202

And you know what, I just realized that we just did compound 4 with the aromatic; we forgot to circle the aromatic ripple on the monosubstituted aromatic; so we can go back to that slide and do that.1213

That would be good, to finally label those.1224

OK, but back to this one: we have sp2; we have sp3; anything at 2,200--any triple bond?1228

Nothing at 2,200; how about 1,700--anything at 1,7000?--for sure, there it is--our biggest, strongest, most obvious peak is our carbonyl, C-O double bond--a carbonyl.1234

OK, so we need something with a carbonyl and an sp2 and an sp3, and something that looks a little strange with this big, broad peak here.1248

Does this maybe look like a carboxylic acid?1262

Remember how a carboxylic acid OH, because it dimerizes, is such a strong hydrogen bonder that it is really, really, really spread out?--that is exactly what we have here.1265

So, in fact, we do have an OH; this is an RCO2H carboxylic acid OH, and it is this whole peak here.1273

It's the OH; so this big, broad peak is our carboxylic acid OH; you could label it as a carboxylic acid OH, if you would like; or you could abbreviate it, RCO2H.1286

It is the OH bond that is stretching, so we label it as an OH peak.1299

And so, this is compound 7; we also must have the carbonyl, if it is a carboxylic acid; we have our sp2 CH; we have our sp3 CH; and what else should we find?1303

That is what I just noticed--we forgot to do that for compound 4: what else should we find?--we have another one of our monosubstituted aromatics; that is getting kind of common here.1315

So, what out-of-plane bends do we expect to see there?--750, 700; there they are...monosubstituted aromatic.1323

OK, and we also get that aromatic ripple, but because we have this carbonyl, it kind of obscured--you didn't see all four peaks here--but there is our little aromatic ripple, too; that pattern is consistent with a monosubstituted aromatic.1336

Very good; OK, how about our next one?1352

We read from left to right: do we have an alcohol (3,300)--do we have an OH?--no OH.1357

What do you see at 3,000?--anything above 3,000, just above 3,000?--nothing there, so there is no sp2 CH.1366

But, just below 3,000, I see this nice, big set of peaks; those are sp3 CH's.1375

Move along; anything at 2,200?--no triple bond; anything at 1,700?--no carbonyl; so we have no triple bond, no carbonyl.1384

Just a little reminder of our systematic approach: what decisions did we just make?--the only significant functional group we have here is an sp3 CH.1397

What does our compound look like?--well, we only have a single alkane with no other interesting functional group here, so it must be compound 5.1406

And remember, every alkane has a very similar IR, because all we are doing is functional group analysis; I can't tell you exactly which alkane this is.1416

All I know is that the only thing present in my sample are sp3 CH's--no other functional groups.1425

That is why this type of a problem, where you are matching it to a set of possible structures, is ideal--because, if I said just "What is the structure of this IR?" you wouldn't be able to answer that definitively.1432

I could ask, "What is a possible structure for this IR?"; but again, it would have hundreds of possible answers--thousands of possible answers; and so, it is a little vague that way.1447

This kind of matching problem is pretty commonly encountered, but make sure that not only do you match it with your structure and draw your structure on here, but that you label your spectrum to show why this is the compound that matches.1457

Oops, I missed a methyl group there.1473

OK, we don't have to worry about anything in this fingerprint region; that is the only thing to label on this spectrum.1475

OK, and last but not least, this is our eighth spectrum, so let's see what we have at 3,300; do we have an OH?--well, we have a broad peak here, but that is kind of a weird shape.1481

An OH is usually a nicely shaped, broad peak; so you know we have something here--let's put an OH with a question mark.1495

Maybe it's water or something like that; it's something weird, so put a little question mark here.1502

OK, now we move to 3,000; what do we have at 3,000?--it looks like we have some peaks above 3,000 (sp2 CH); it looks like we have some peaks below 3,000 (those are sp3 CH).1508

So, we have both of those.1522

Let's look at 2,200--any triple bonds?--no triple bonds.1524

Let's look at 1,700--at 1,700, it sure is...right there, a big, big peak; we must have a carbonyl in this compound.1528

Let's take a look at our structures and decide what possibilities we have.1539

OK, we need an sp2 CH and an sp3 CH; do we have an aromatic?--we don't have any other alkenes in this example, right?--so the sp2 CH is coming from our aromatic.1547

All of these happen to be monosubstituted aromatic, so we have our 700 and 750.1561

Let me go ahead and find that, because that is the only way I can get my sp2 CH.1571

It can't be 1, because 1 only has the sp3 CH; so we're coming back down to these; those are our only two possibilities; they both have carbonyls; they both have sp3 CH; they both have sp2 CH.1577

How do we distinguish between these two?--we have an aldehyde and a ketone; what is the determining factor?1590

Here it is: that aldehyde CH is very unique; when you have an aldehyde, how are you going to find that?--you are going to look for little vampire fangs at 2,850 and 2,750.1597

And they are going to be hard to find typically (we overlook them a lot), but here they are; here is one at 2,750, and here is one at 2,830 1, 2.1611

These two peaks are my aldehyde CH: so actually, my sp3 CH--I labeled it incorrectly here at first; it only goes out to here, because these last two are the aldehyde CH.1620

And so, it is not obvious at first; but when we look for it, we can pick out an aldehyde pretty well--especially the one at 2,750; it usually stands alone; the 2,850 is usually touching the sp3, so it's a little harder to see.1636

OK, so this, in fact, is structure #3.1651

Very good; but 3 doesn't have an alcohol--it doesn't have an OH; so what is this big, messy peak here--why do we have this?1657

I mean, it could be water from our sample, but what else do we have?1664

Remember, when we have a carbonyl, very often we see this overtone around 3,400, and sometimes it is really big overtone; so it's that, plus maybe a combination of some water; so we can ignore it.1668

It is not an OH; it is just our carbonyl overtone.1680

This is consistent with the aldehyde structure given.1686

Now, another type of problem we can have, besides a matching sort of problem--I mean, there are all sorts of problems you can have; but here is another example.1692

Let's say we used IR to analyze our product after we ran a reaction.1700

Now again, this is a very common scenario, because IR spectrometers are very affordable; and so, it is one of the major pieces of equipment that you will have in almost every organic lab.1704

So, it is a routine part of analysis, after you do a reaction and isolate your product, to take an IR of that product as a way of identifying what compound you have.1717

Now, if that IR spectrum is going to tell you whether or not your reaction worked, you have to know what to expect from the IR; so you need to be able to predict it.1729

Let's take a look at some sample reactions and see how you could use IR to tell whether or not this reaction had gone to completion, or was successful.1739

So, to be complete--that means all of your starting material is gone and all of your product is present.1753

The only thing present is your product; so that assumes that the reaction has run its course; you have isolated your product; you have purified your product somewhat; and we are looking for this as our product.1760

What we can ask is, "Well, what peaks are going to be new in the IR spectrum--what is going to show up? What peaks are going to disappear that used to be in the starting material?"1771

So, if you compare the IR of the starting material to the IR of the product, what changes would there be?--this is, again, a very common analysis that we are going to be doing after running a reaction in an organic lab.1781

What do you expect to be different--do you find different in the starting material and the product?1792

And again, this is maybe a good point to pause it and try some of these problems on your own, and then we can work through it together.1798

Well, clearly, we have a carbonyl here that is missing in our product--that is gone in our product; so our carbonyl, which is around 1,700, should disappear.1805

If our reaction was successful, there should be no carbonyl peak in our product.1819

What else can we look for?--well, we should now have an OH that we didn't have before.1823

So, our OH around 3,300 appears; that is something new.1829

Perhaps we can look for a C-O single bond; there is no C-O single bond in our structure before, so we can maybe look for that around 1,050.1837

It's a little harder to find in that fingerprint region, but we can maybe find that as well.1846

OK, but remember, if our sample is just wet, we might find that we have the OH peaks in there, even though we have not made an alcohol.1852

That is why it is important to also check that the carbonyl peak is absent; and that way, we know if we have an organic product, we must have converted our starting material to something; and that gives us evidence that the OH is actually part of our structure.1860

OK, how about the next one--what changes have taken place, and what changes that have taken place are significant in the IR?1875

How would it present itself in the IR spectrum?1884

We have gotten rid of this double bond; we used to have a double bond, and now it's gone.1888

So, how does that affect the IR?--well, the IR of the starting material--how do you see evidence of that double bond?1892

True, the carbon-carbon double bond might be there, but that is kind of a weak signal; what is a much more significant signal is the sp2 CH that is here and here.1899

Those bonds stretching are going to be very obvious in the IR; and so we want those to disappear, because there is no sp2 hybridized CH in the product.1909

OK, that is going to be the biggest one; we could put also the carbon-carbon double bond disappearing, but that is not going to be nearly as significant, because that might not have been a significant peak to start off with.1921

OK, anything else?--we had a carbonyl; we still have a carbonyl; but because this carbonyl was conjugated, the new carbonyl in the product, or the carbonyl that is now in the product, is going to be at a different wavenumber.1935

So, let's just say the carbonyl moves; it is going to be at a different peak, and it is going to...when you have conjugation, that is something that lowers the number, so this is actually going to be a higher reciprocal centimeter.1952

It is going to move to the left, because we have gotten rid of that double bond; so a subtle difference, but it also will be a difference that we should observe, if this reaction was successful.1970

What if we did this substitution reaction--we had a bromine here, and now it is a nitrile?1983

OK, is there anything in the starting material that is unique--do we know how to identify a bromine in an IR?1990

We have not talked about halides in the IR, and that is because they are not very diagnostically useful; this carbon-bromine bond will stretch, but it is something that either is weak in intensity or comes in the fingerprint region or so on.1998

So, there is nothing significant here; we have sp3 hybridized carbons; we still have sp3 hybridized carbons; so there is nothing significant to note in our starting material that is going to disappear.2016

But how would we tell if we had this nitrile--what does this structure look like, when you have a C-N group?2028

What does that look like?--to have four bonds, it must be a C, triple bond, N, right?--and that triple bond is something that we can pick out in the IR.2038

So, what is going to show up?--the C, triple bond, N--the nitrile--is going to appear; it appears at around 2,200.2045

So, if we have that peak showing up after we have isolated our organic product, then that confirms that we must have synthesized the nitrile.2055

OK, and how about our next one?--we had an alkene, and now we have an ether.2065

We haven't really talked about ethers specifically; we haven't seen any examples of ethers; but what is interesting in the ether?2070

What peaks would you predict for this product--what kinds of CH's?2078

This CH3 and this CH3 and this CH, CH2, CH2...all of those are the same by IR: they are sp3 CH's, just below 3,000.2083

OK, but we already had those--we already had sp3 CH's--so that is not going to be something new.2097

We can just mention they are still there, so that is not too big of a deal; but what is going to be new--what is going to be different?2103

Well, perhaps we can find our C-O: we have a C-O bond here; we have a C-O bond here.2111

So, we might actually see those separately--so maybe a C-O around 1,050.2117

Sometimes those are obvious.2123

But what is the really significant change that is going to happen--what did we have in our starting material that is now gone?2126

We had an sp2 hybridized carbon; so we have sp2 CH's just above 3,000 that are going to disappear.2131

There should be no more of those in our product; so that is going to be the big change that is going to be happening.2141

OK, let's look at this multi-step transformation as we go from an alcohol to an aldehyde to a carboxylic acid; these are oxidation reactions.2152

How would our IR change as we move along--what are the most significant changes?2161

Well, in our alcohol, we have an OH peak around 3,300; that is always an obvious peak, and that is going to disappear.2167

If we oxidize this to an aldehyde, what would our aldehyde product show?2179

It is going to show the carbonyl, which is always significant--a large peak at 1,700--a very strong signal.2185

And what else should be new?--this aldehyde CH is a significant peak that will be unique: that is our little double set of peaks, 2,850 and 2,750--small, but they are there, and you can look for those.2192

And then, if we were to oxidize this further to carboxylic acid, what is going to happen?2213

We are still going to have a carbonyl; our carbonyl is going to shift to a different wavenumber--you can take a look at a table of carbonyl shifts to see how an aldehyde compares to a carboxylic acid.2218

So, the carbonyl will still be there, but its wavenumber is likely to be different.2231

Of course, we are going to have this OH; it is going to be a carboxylic acid OH, which means it is going to be from 3,400 all the way down to 2,400--really, really broad.2236

So, instead of having a nice little OH, you are going to have a big, spread-out OH.2249

That is how we know we have a carboxylic acid.2253

Anything else significant here?--well, our aldehyde C-H should be gone; the aldehyde C-H disappears.2256

That is how you can tell, maybe, that not only do I have some of my product--sometimes a reaction doesn't go to completion; so you have some product, but you also still have some starting material left.2268

The IR could maybe tell you if you have a significant amount of starting material: you would see both the carboxylic acid peaks and the aldehyde peaks, so that you could maybe see that you have a mixture there.2278

So, it is not always just one or the other; but to have this product (carboxylic acid) pure means there should no longer be an aldehyde CH, and we should have the OH on the carbonyl.2288

OK, here is another multistep transformation: we go from this alkyne to this alkyne, and then an alkyne to an alkene; how can we follow that by IR and verify that these reactions have worked?2303

Well, there is a big difference between these two alkynes; what is the big difference there?2321

They both have a carbon-carbon triple bond; we will see that in this first structure (this is around 2,200); but in this compound, because we have symmetrically substituted triple bond (we have the same group on either side), what happens to a bond when it is totally symmetrical?2327

And there is no change in dipole when you stretch that bond; what happens to the absorption of the IR?2353

It doesn't happen: there is no absorption of the IR, which means there is no signal in the IR spectrum.2358

We would expect this carbon-carbon triple bond peak to disappear.2364

We'll put a little question mark there, because we don't know for sure that is going to happen; but that could be very likely, and we would predict that to happen, and that is because it is symmetrically substituted.2370

OK, so I wouldn't be surprised if our triple bond went away; but what other change is taking place?2386

There is something else that is special about this triple bond; when you have a terminal alkyne, it is called "terminal" because it's at the end of a chain, and when you are at the end of the carbon chain, what does this carbon have on it?2392

It has a hydrogen on it.2405

This is an internal alkyne, which means it has a carbon group on the other side; there is no CH.2407

So, would that CH show up in the IR spectrum?--it absolutely would: it's an sp hybridized CH, and that comes somewhere around 3,300; that is the sharp peak we sometimes see at around 3,300.2417

And it would be in our starting material; it would not be in our product; so our sp CH, for sure, disappears, because it is no longer there.2430

They both have sp3 CH's, so this methyl group in each of them means we have our normal peak below 3,000; so that is not going to be useful to us--it's going to appear in both cases.2444

OK, but then, if we took that alkyne and we converted this to an alkene, this is a trans-1,2-disubstituted alkene.2456

I'm explaining, and I'm looking at the detail of this substitution pattern, because, just like in a benzene ring, when you have monosubstituted, or ortho, or meta, or para, you can see a difference in those substitution patterns; you can pick that out for a benzene ring.2467

It turns out, you can also do the same thing for an alkene; I'm not going to...again, this is kind of more of an advanced IR topic; it is not often covered at the introductory level.2487

But just to let you know, you can still have those interesting bending motions; we can see that substitution pattern, kind of in that same region around 1,000 reciprocal centimeters.2495

So, it's in the fingerprint region; it's not something we would notice right away; but we can look for it, and trans is going to be different from a cis, is going to be different from a monosubstituted alkene, and so on.2511

OK, but if we didn't know to look for those bending patterns, what differences would we expect to find here, in going from the alkyne to the alkene?2524

Well, it is these hydrogens that are significant; and those show up--it is the stretching of those C-H bonds that is significant.2534

We are going to see these sp2 CH's appear, and where does that come?--that is the one that is just above 3,000.2541

OK, so we would be able to follow this multistep transformation by IR.2552

OK, and finally, just a little more challenging problem here: let's look at all of these alcohols and see if we can predict how to distinguish them by their IR's--because, clearly, they all have OH's, so they are all going to have that peak around 3,300; so they all have the OH stretch around 3,300, so that is not going to be something that is going to be useful to us.2558

We should be able to identify when we have an alcohol, but what if we had different types of alcohols--how can we look for ways to distinguish them?2586

OK, and it's going to have to come from the rest of the molecule--what else is in the molecule?2597

We have a benzene ring here; so what significant peaks do we see for the benzene ring?2600

We have...what type of CH's do we have?--we have sp2 CH's, and those are just above 3,000; and because it's monosubstituted, we expect to have our peaks at...a monosubstituted aromatic is around 750 and 690.2607

We have those out-of-plane bending, so we would expect to find those; and that is going to be different from this one, because this next one also has sp2 CH just above 3,000, but what else does it have--any other CH's?2637

We have this CH3 and this CH2; we also have the sp3 CH's that occur just below 3,000.2655

That would be a way to distinguish between these two.2665

What would be another difference that you would find in their spectra?--is this a monosubstituted aromatic?2667

No, this is a disubstituted aromatic; and what do we call it when they are 1,4 like this (1, 2, 3, 4--when they are opposite)?--we call that para.2675

We have a para substituted aromatic; and where do those peaks show up?--there is just a single peak somewhere around 815; so that pattern is going to be different than the monosubstituted; that little aromatic ripple region around 2,000 is going to look at little different, as well.2685

OK, so we can distinguish, just based on substitution patterns, too.2702

And how does this one differ from this one?--we have this (this is phenol, actually, when you have a benzene ring with an OH) phenol; how is that different--why is this a different structure?2708

We are missing the double bond; so this is not benzene any longer--this is just cyclohexane.2718

And so, what kind of CH's do we have here?--we have just sp3 CH's--just below 3,000.2725

So, in this case, we have only sp2; here we have only sp3; and in this case, we have both sp2 and sp3.2733

OK, is this a monosubstituted aromatic?--this is not a monosubstituted aromatic; this is...just a little note here; just a little reminder--this is not aromatic, because there are no π bonds.2742

You need to have those three π bonds (1, 2, 3) to make a benzene.2755

So, every time we talked about "aromatic" (the aromatic ripple, the substitution patterns, ortho/meta/para, and so on), we were always talking about benzene in particular with those three π bonds.2759

OK, and how about this last one--how is this going to be distinguished; what kind of CH's do we have?2771

We have the double bonds; so we see sp2 CH's just above 3,000; and we have a regular alkyl, sp3 CH, just below 3,000.2777

So, it is similar to this second compound in that it has both sp2 and sp3; so how could we tell the difference?2791

This is where we are really going to have to dig into that fingerprint region and pick out those out-of-plane bendings.2801

Here, you would have the para substituted at 815; here you would not--there is no para; OK.2807

But what we do have is an alkene; I would describe this alkene as a monosubstituted alkene; it has just one carbon group on it.2816

And a monosubstituted alkene has peaks that we can look for; we can look for those bending patterns.2829

OK, so to do this problem, it really relies on some of the advanced knowledge of IR, in order to distinguish between these two.2838

In order to distinguish between the three cyclic compounds, it can really just be done by looking at the sp2 versus sp3 CH's and the type of CH's you have in your structure.2847

OK, so I think we have had a pretty good introduction into the theory of IR and the application of IR.2859

This is an incredible important technique that you are going to be using throughout organic chemistry laboratory; and in fact, it is typically taught as one of the first spectroscopies.2864

And on this, you will be building some additional ones, such as NMR spectroscopy; and a lot of times, spectra problems are going to be combinations.2875

You will get some IR data, and then you will also get some NMR data, and you have to use them together to come up with a structure.2887

Any time you are given an IR spectrum, what you are going to be getting from that is what functional groups are present: do we have an OH?--do we have a carbonyl?--do we have an aromatic ring?--etc.2893

And if given a correlation table, you should be able to pick up those functional groups with confidence.2904

Thanks very much, and I hope to see you again soon.2911