Dr. Laurie Starkey brings in her love of organic chemistry and helps students learn through visual models and real world examples. Focusing on Chemical Structures, she covers topics from Alkanes to Aldehydes and Amines. This course is crucial for students who wish to excel in Organic Chemistry in order to satisfy their degree or pre-medical requirements. Lessons go in depth and are followed with numerous examples similar to those found on organic chemistry exams and qualifying tests. Additional topics include everything from Stereochemistry to Nomenclature and Spectroscopy. Dr. Laurie Starkey is also the author of “Introduction to Strategies for Organic Synthesis” (Wiley) and earned her Ph.D. in Chemistry from UCLA. She has been teaching Organic Chemistry at the university level for over 15 years and most recently won the 2013 Provost's Award for Excellence in Teaching, Cal Poly Pomona's highest teaching award.

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Table of Contents
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Part I
	Introduction and Drawing Structures			49:51
		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			44:25
		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			67:46
		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		60:45
			Common Acids/Bases	60:46
			Example: Determine the Direction of Equilibrium	64:51
	Structures and Properties of Organic Molecules			83:35
		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		63:11
			Van Der Waals/ London Forces	63:12
			Example: Van Der Waals/ London Forces	64:59
		Water Solubility		68:32
			Water Solubility	68:34
			Example: Water Solubility	69:05
			Example: Acetone	71:29
		Isomerism		73:51
			Definition of Isomers	73:53
			Constitutional Isomers and Example	74:17
			Stereoisomers and Example	75:34
		Introduction to Functional Groups		77:06
			Functional Groups: Example, Abbreviation, and Name	77:07
		Introduction to Functional Groups		80:48
			Functional Groups: Example, Abbreviation, and Name	80:49
	Alkane Structures			73:38
		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	62:14
		Cyclohexane Chair Flips		64:06
			Axial and Equatorial Groups	64:10
			Example: Chair Flip on Methylcyclohexane	66:44
		Cyclohexane Conformations Example		69:01
			Chair Conformations of cis-1-t-butyl-4-methylcyclohexane	69:02
	Stereochemistry			100:54
		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	61:48
		Drawing Stereoisomers		66:37
			Draw All Stereoisomers of 2,3-dichlorobutane	66:38
		Molecules with Two Chiral Centers		70:22
			Draw All Stereoisomers of 2,3-dichlorobutane, cont.	70:23
		Optical Activity		74:10
			Chiral Molecules	74:11
			Angle of Rotation	74:51
			Achiral Species	76:46
		Physical Properties of Stereoisomers		77:11
			Enantiomers	77:12
			Diastereomers	78:01
			Example	78:26
		Physical Properties of Stereoisomers		83:05
			When Do Enantiomers Behave Differently?	83:06
		Racemic Mixtures		88:18
			Racemic Mixtures	88:21
			Resolution	89:52
		Unequal Mixtures of Enantiomers		92:54
			Enantiomeric Excess (ee)	92:55
		Unequal Mixture of Enantiomers		94:43
			Unequal Mixture of Enantiomers	94:44
			Example: Finding ee	96:38
			Example: Percent of Composition	99:46
	Nomenclature			113:47
		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		65:02
			Aromatic Nomenclature and Examples	65:03
		Aromatic Nomenclature, cont.		69:09
			Ortho, Meta, and Para	69:10
		Aromatic Nomenclature, cont.		73:27
			Common Names for Simple Substituted Aromatic Compounds	73:28
		Carboxylic Acid Nomenclature		76:35
			Carboxylic Acid Nomenclature and Examples	76:36
		Carboxylic Acid Derivatives		82:28
			Carboxylic Acid Derivatives	82:42
			General Structure	83:10
		Acid Halide Nomenclature		84:48
			Acid Halide Nomenclature and Examples	84:49
		Anhydride Nomenclature		88:10
			Anhydride Nomenclature and Examples	88:11
		Ester Nomenclature		92:50
			Ester Nomenclature	92:51
			Carboxylate Salts	98:51
		Amide Nomenclature		100:02
			Amide Nomenclature and Examples	100:03
		Nitrile Nomenclature		105:22
			Nitrile Nomenclature and Examples	105:23
	Chemical Reactions			51:01
		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			26:23
		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			108:05
		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?		60:40
			Example 1: SN1 or SN2 Mechanisms	60:42
			Example 2: SN1 or SN2 Mechanisms	63:00
			Example 3: SN1 or SN2 Mechanisms	64:06
			Example 4: SN1 or SN2 Mechanisms	66:17
		SN1 Mechanism		69:12
			Three Steps of SN1 Mechanism	69:13
		SN1 Carbocation Rearrangements		74:50
			Carbocation Rearrangements Example	74:51
		SN1 Carbocation Rearrangements		80:46
			Alkyl Groups Can Also Shift	80:48
		Leaving Groups		84:26
			Leaving Groups	84:27
			Forward or Reverse Reaction Favored?	86:00
		Leaving Groups		89:59
			Making poor LG Better: Method 1	90:00
		Leaving Groups		94:18
			Making poor LG Better: Tosylate (Method 2)	94:19
		Synthesis Problem		98:15
			Example: Provide the Necessary Reagents	98:16
		Nucleophilicity		101:10
			What Makes a Good Nucleophile?	101:11
		Nucleophilicity		104:45
			Periodic Trends: Across Row	104:47
			Periodic Trends: Down a Family	106:46
	Elimination Reactions			71:43
		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	60:00
			Example 2: Predict the Product	62:10
			Example 3: Predict the Product	64:07
		Predict the Product: SN2 vs. E2		66:06
			Example 4: Predict the Product	66:07
			Example 5: Predict the Product	67:29
			Example 6: Predict the Product	67:51
			Example 7: Predict the Product	69:18
Part II
	Alkenes			36:39
		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			128:44
		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	60:08
		Halohydrin: Regiochemistry		63:55
			Halohydrin: Regiochemistry	63:56
			Bromonium Ion Intermediate	64:26
		Example		69:28
			Example: Predict Major Product	69:29
		Example Cont.		70:59
			Example: Predict Major Product Cont.	71:00
		Catalytic Hydrogenation of Alkenes		73:19
			Features of Catalytic Hydrogenation	73:20
		Catalytic Hydrogenation of Alkenes		74:48
			Metal Surface	74:49
			Heterogeneous Catalysts	75:29
			Homogeneous Catalysts	76:08
		Catalytic Hydrogenation of Alkenes		77:44
			Hydrogenation & Pi Bond Stability	77:45
			Energy Diagram	79:22
		Catalytic Hydrogenation of Dienes		80:40
			Hydrogenation & Pi Bond Stability	80:41
			Energy Diagram	83:31
		Example		84:14
			Example: Predict Product	84:15
		Oxidation of Alkenes		87:21
			Redox Review	87:22
			Epoxide	90:26
			Diol (Glycol)	90:54
			Ketone/ Aldehyde	91:13
		Epoxidation		92:08
			Epoxidation	92:09
			General Mechanism	96:32
		Alternate Epoxide Synthesis		97:38
			Alternate Epoxide Synthesis	97:39
		Dihydroxylation		101:10
			Dihydroxylation	101:12
			General Mechanism (Concerted Via Cycle Intermediate)	102:38
		Ozonolysis		104:22
			Ozonolysis: Introduction	104:23
			Ozonolysis: Is It Good or Bad?	105:05
			Ozonolysis Reaction	108:54
		Examples		111:10
			Example 1: Ozonolysis	111:11
			Example	113:25
		Radical Addition to Alkenes		115:05
			Recall: Free-Radical Halogenation	115:15
			Radical Mechanism	115:45
			Propagation Steps	118:01
			Atom Abstraction	118:30
			Addition to Alkene	119:11
		Radical Addition to Alkenes		119:54
			Markovnivok (Electrophilic Addition) & anti-Mark. (Radical Addition)	119:55
			Mechanism	121:03
		Alkene Polymerization		125:35
			Example: Alkene Polymerization	125:36
	Alkynes			73:19
		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		61:07
		Example 3: Transform		66:22
	Alcohols, Part I			59:52
		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			45:35
		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
	Ethers			94:45
		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		61:03
			Transformation	61:04
		Regiochemistry of Epoxide Ring Openings		65:29
			Regiochemistry of Epoxide Ring Openings in Base	65:30
			Regiochemistry of Epoxide Ring Openings in Acid	67:34
		Example		70:26
			Example 1: Epoxide Ring Openings in Base	70:27
			Example 2: Epoxide Ring Openings in Acid	72:50
		Reactions of Epoxides with Grignard and Hydride		75:35
			Reactions of Epoxides with Grignard and Hydride	75:36
		Example		81:47
			Example: Ethers	81:50
		Example		87:01
			Example: Synthesize	87:02
	Thiols and Thioethers			16:50
		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
	Transformation Practice Problems			38:58
		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
	Ketones			138:12
		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		61:43
			Predict	61:44
			Mechanism	63:08
		Mechanism for Acetal Formation		64:10
			Mechanism for Acetal Formation	64:11
		What is a CTI?		75:04
			Tetrahedral Intermediate	75:05
			Charged Tetrahedral Intermediate	75:45
			CTI: Acid-cat	76:10
			CTI: Base-cat	77:01
		Acetals & Cyclic Acetals		77:49
			Overall	77:50
			Cyclic Acetals	78:46
		Hydrolysis of Acetals: Regenerates Carbonyl		80:01
			Hydrolysis of Acetals: Regenerates Carbonyl	80:02
			Mechanism	82:08
		Reaction with Nitrogen Nu:		90:11
			Reaction with Nitrogen Nu:	90:12
			Example	92:18
		Mechanism of Imine Formation		93:24
			Mechanism of Imine Formation	93:25
		Oxidation of Aldehydes		98:12
			Oxidation of Aldehydes 1	98:13
			Oxidation of Aldehydes 2	99:52
			Oxidation of Aldehydes 3	100:10
		Reductions of Ketones and Aldehydes		100:54
			Reductions of Ketones and Aldehydes	100:55
			Hydride/ Workup	101:22
			Raney Nickel	102:07
		Reductions of Ketones and Aldehydes		103:24
			Clemmensen Reduction & Wolff-Kishner Reduction	103:40
		Acetals as Protective Groups		106:50
			Acetals as Protective Groups	106:51
		Example		110:39
			Example: Consider the Following Synthesis	110:40
		Protective Groups		114:47
			Protective Groups	114:48
		Example		119:02
			Example: Transform	119:03
		Example: Another Route		124:54
			Example: Transform	128:49
		Example		128:50
			Transform	128:51
		Example		131:05
			Transform	131:06
		Example		133:45
			Transform	133:46
		Example		135:43
			Provide the Missing Starting Material	135:44
Part III
	Carboxylic Acids			77:51
		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		63:06
			Ester Hydrolysis Requires Acide or Base	63:07
		Nitrile Hydrolysis		65:22
			Nitrile Hydrolysis	65:23
		Nitrile Hydrolysis Mechanism		66:53
			Nitrile Hydrolysis Mechanism	66:54
		Use of Nitriles in Synthesis		72:39
			Example: Nitirles in Synthesis	72:40
	Carboxylic Acid Derivatives			81:04
		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		61:41
			A) Hydride Nu: Review	61:42
			A) Hydride Nu: Sodium Borohydride + Ester	62:43
		Reactions of Carboxylic Acid Derivatives with Nucleophiles		63:57
			Lithium Aluminum Hydride (LAH)	63:58
			Mechanism	64:29
		Summary of Hydride Reductions		67:09
			Summary of Hydride Reductions 1	67:10
			Summary of Hydride Reductions 2	67:36
		Hydride Reduction of Amides		68:12
			Hydride Reduction of Amides Mechanism	68:13
		Reaction of Carboxylic Acid Derivatives with Organometallics		72:04
			Review 1	72:05
			Review 2	72:50
		Reaction of Carboxylic Acid Derivatives with Organometallics		74:22
			Example: Lactone	74:23
		Special Hydride Nu: Reagents		76:34
			Diisobutylaluminum Hydride	76:35
			Example	77:25
			Other Special Hydride	78:41
		Addition of Organocuprates to Acid Chlorides		79:07
			Addition of Organocuprates to Acid Chlorides	79:08
	Enols and Enolates, Part 1			86:22
		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		60:55
			Crossed/Mixed Aldol & Compound with α H's	60:56
			Ketone vs. Aldehyde	62:30
			Crossed/Mixed Aldol & Compound with α H's Continue	63:10
		Crossed/Mixed Aldol		65:21
			Mixed Aldol: control Using LDA	65:22
		Crossed/Mixed Aldol Retrosynthesis		68:53
			Example: Predic Aldol Starting Material (Aldol Retrosyntheiss)	68:54
		Claisen Condensation		72:54
			Claisen Condensation (Aldol on Esters)	72:55
		Claisen Condensation		79:52
			Example 1: Claisen Condensation	79:53
		Claisen Condensation		82:48
			Example 2: Claisen Condensation	82:49
	Enols and Enolates, Part 2			50:57
		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
	Aromatic Compounds: Structure			60:59
		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			84:04
		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		62:24
			Electrophilic Aromatic Substitution: Friedel-Crafts Alkylation	62:25
			Example & Mechanism	63:37
		Friedel-Crafts Alkylation Drawbacks		65:48
			A) Can Over-React (Dialkylation)	65:49
		Friedel-Crafts Alkylation Drawbacks		68:21
			B) Carbocation Can Rearrange	68:22
			Mechanism	69:33
		Friedel-Crafts Alkylation Drawbacks		73:35
			Want n-Propyl? Use Friedel-Crafts Acylation	73:36
			Reducing Agents	76:45
		Synthesis with Electrophilic Aromatic Substitution		78:45
			Example: Transform	78:46
		Synthesis with Electrophilic Aromatic Substitution		80:59
			Example: Transform	81:00
	Aromatic Compounds: Reactions, Part 2			59:10
		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
	Conjugated Dienes			69:12
		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		61:27
			Explain Why No Diels-Alder Reaction Takes Place in This Case	61:28
		Diels-Alder Reaction		63:09
			Example: Predict	63:10
		Diels-Alder Reaction: Synthesis Problem		65:39
			Diels-Alder Reaction: Synthesis Problem	65:40
	Amines			34:58
		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
			1) Reaction with Ketone/Aldehyde: 1° Amine (RNH2)	17:43
		Reaction of Amines		18:48
			1) 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
			2) 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
Part IV
	Infrared Spectroscopy, Part I			64:00
		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		18:2
			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	60:52
			Example 8	62:20
	Infrared Spectroscopy, Part II			48:34
		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			92:14
		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'		61:24
			Understanding Splitting Patterns: The 'n+1 Rule'	61:25
		Explanation of n+1 Rule		62:42
			Explanation of n+1 Rule: One Neighbor	62:43
			Explanation of n+1 Rule: Two Neighbors	66:23
		Summary of Splitting Patterns		66:24
			Summary of Splitting Patterns	70:45
		Predicting ¹H NMR Spectra		70:46
			Example 1: Predicting ¹H NMR Spectra	73:30
			Example 2: Predicting ¹H NMR Spectra	79:07
			Example 3: Predicting ¹H NMR Spectra	83:50
			Example 4: Predicting ¹H NMR Spectra	89:27
	Nuclear Magnetic Resonance (NMR) Spectroscopy, Part II			123:48
		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)	62:40
			Allylic (4-bond) and W-coupling (4-bond) (Rigid Structures Only)	64:05
		¹H NMR Advanced Splitting Patterns		65:39
			Example 1: ¹H NMR Advanced Splitting Patterns	65:40
			Example 2: ¹H NMR Advanced Splitting Patterns	70:01
			Example 3: ¹H NMR Advanced Splitting Patterns	73:45
		¹H NMR Practice		82:53
			¹H NMR Practice 5: C₁₁H₁₇N	82:54
			¹H NMR Practice 6: C₉H₁₀O	94:04
		¹³C NMR Spectroscopy		104:49
			¹³C NMR Spectroscopy	104:50
		¹³C NMR Chemical Shifts		107:24
			¹³C NMR Chemical Shifts Part 1	107:25
			¹³C NMR Chemical Shifts Part 2	108:59
		¹³C NMR Practice		110:16
			¹³C NMR Practice 1	110:17
			¹³C NMR Practice 2	118:30

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