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Organic Chemistry (Updated in 2018)
Summary of Organic Reactions
Summary of Organic Reactions
Chapter 1 - Electrons, Bonding, and Molecular Properties
Chapter 1 Slides
1.1 Lewis Structures (11:04)
1.2 Formal Charges (4:10)
1.3 Valence Bond Theory and Hybridization (17:29)
1.4 Molecular Orbital Theory (14:14)
1.5 Polarity (6:38)
1.6 Intermolecular Forces (20:16)
Chapter 2 - Molecular Representations and Resonance
Chapter 2 Slides
2.1 Condensed Structures (11:36)
2.2 Bond-Line Structures (15:25)
2.3a Resonance (17:40)
2.3b Resonance and Hybridization (5:33)
Chapter 3 - Acids and Bases
Chapter 3 Slides
3.1 Introduction to Acids and Bases (9:01)
3.2 Ranking Bases (14:51)
3.3 Ranking Acids (8:28)
Chapter 4 - Alkanes
Chapter 4 Part 1 Slides - Nomenclature of Alkanes
Chapter 4 Part 2 Slides - Constitutional Isomers and Conformations of Alkanes
4.1a Nomenclature of Alkanes (15:32)
4.1b Nomenclature of Cycloalkanes (8:20)
4.1c Systematic Nomenclature of Complex Substituents (4:22)
4.1d Common Names of Complex Substituents (7:52)
4.1e Nomenclature of Bicyclic Compounds (5:44)
4.2 Drawing Constitutional Isomers (6:18)
4.3 Newman Projections (8:20)
4.4 Cycloalkanes and Cyclohexane Chair Conformations (22:38)
Chapter 5 - Isomers and Stereochemistry
Chapter 5 Slides
5.1 Overview of Isomerism (7:23)
5.2 Chiral Centers and Chirality (5:22)
5.3 Absolute Configurations - Assigning R and S (14:46)
5.4 Molecules with Multiple Chiral Centers (15:15)
5.5 Fischer Projections (6:13)
5.6 Determining the Relationship Between a Pair of Molecules (6:43)
5.7 Amine Inversion and Chiral Molecules Without Chiral Centers (5:23)
5.8 Optical Activity (7:39)
Chapter 6 - Introduction to Organic Reactions and Mechanisms
Chapter 6 Slides
6.1 Reaction Enthalpies and Bond Dissociation Energies (6:11)
6.2 Entropy, Gibbs Free Energy, and the Equilibrium Constant (9:43)
6.3 The Kinetics of Organic Reactions (4:41)
6.4 Nucleophiles, Electrophiles, and Intermediates (5:43)
6.5 Reaction Mechanisms and Curved Arrow Pushing (7:11)
Chapter 7 - Substitution and Elimination Reactions of Alkyl Halides
Chapter 7 Part 1 - Slides
Chapter 7 Part 2 Slides
7.1a Introduction to SN2 Reactions (9:14)
7.1b Factors Affecting SN2 Reactions (11:39)
7.2a Introduction to SN1 Reactions (4:44)
7.2b Carbocation Rearrangements in SN1 Reactions (8:29)
7.2c Racemization in SN1 Reactions (1:36)
7.2d Factors Affecting SN1 Reactions (4:50)
7.3 Unreactivity of Vinyl and Aryl Halides (2:08)
7.4 Predicting the Products of Substitution Reactions (18:04)
7.5 Nomenclature of Alkenes (15:17)
7.6 Stability of Alkenes (2:17)
7.7a Introduction to E2 Elimination Reactions (6:41)
7.7b Exceptions to Zaitsev's Rule for E2 Reactions (8:37)
7.7c The Stereospecificity of E2 Reactions -- Anti-periplanar (10:40)
7.8 Introduction to E1 Elimination Reactions (4:54)
7.9 Predicting the Products of Elimination Reactions (10:01)
7.10 Distinguishing Between Substitution and Elimination Reactions (16:52)
Chapter 8 - Addition Reactions to Alkenes
Chapter 8 Slides
8.1 Introduction to Alkene Addition Reactions (4:00)
8.2 Hydrohalogenation (5:07)
8.3a Hydration -- Acid-Catalyzed Hydration (3:24)
8.3b Hydration -- Oxymercuration-Demercuration (6:06)
8.3c Hydration -- Hydroboration-Oxidation (4:14)
8.4a Acid-Catalyzed Addition of an Alcohol (2:24)
8.4b Alkoxymercuration-Demercuration (1:15)
8.5 Catalytic Hydrogenation (3:17)
8.6a Halogenation (3:54)
8.6b Halohydrin Formation (3:19)
8.7a Anti-Dihydroxylation (4:11)
8.7b Syn-Dihydroxylation (2:39)
8.8 Predicting the Products of Alkene Addition Reactions (10:17)
8.9 Oxidative Cleavage -- Ozonolysis and Permanganate Cleavage (4:49)
Chapter 9 - Alkynes
Chapter 9 Slides
9.1 Nomenclature of Alkynes (3:47)
9.2 Acidity of Alkynes (2:31)
9.3 Preparation of Alkynes (2:57)
9.4 Reduction of Alkynes (6:00)
9.5 Introduction to Addition Reactions of Alkynes (2:18)
9.6 Hydrohalogenation (3:16)
9.7 Halogenation (1:34)
9.8a Acid-Catalyzed Hydration (4:09)
9.8b Hydroboration-Oxidation (5:06)
9.8c Keto-Enol Tautomerization (3:57)
9.9 Ozonolysis (1:19)
9.10 Alkylation of Acetylide Ions (2:20)
Chapter 10 - Radical Reactions
Chapter 10 Slides
10.1 Introduction to Free Radical Halogenation (4:01)
10.2 Free Radical Chlorination vs Bromination (5:51)
10.3 The Mechanism of Free Radical Halogenation (7:51)
10.4 Allylic and Benzylic Bromination Using NBS (7:13)
10.5 Hydrobromination of Alkenes with Peroxide (4:22)
Chapter 11 - Synthesis
Chapter 11 Slides
11.1 Functional Group Conversions (4:18)
11.2 Increasing the Length of the Carbon Skeleton (8:06)
11.3 Decreasing the Length of the Carbon Chain or Opening a Ring (2:42)
11.4a Common Patterns in Synthesis Part 1 (5:24)
11.4b Common Patterns in Synthesis Part 2 (8:50)
11.4c Common Patterns in Synthesis Part 3 (5:20)
11.4d Common Patterns in Synthesis Part 4 (9:45)
Chapter 12 - Alcohols
Chapter 12 Slides
12.1 Introduction to and Nomenclature of Alcohols (4:46)
12.2 Acidity of Alcohols and Phenols (13:06)
12.3a Synthesis of Alcohols; Reduction of Ketones and Aldehydes (8:05)
12.3b Synthesis of Alcohols; Grignard Addition (8:18)
12.4 Protecting Alcohols (5:43)
12.5a Substitution with HCl, HBr, and HI (4:21)
12.5b Substitution with PBr3 and SOCl2 (5:04)
12.5c Formation of Tosylate Esters (3:36)
12.6 Elimination (Dehydration) (3:13)
12.7 Oxidation with Chromic Acid and PCC (9:24)
12.8 Patterns in Synthesis (8:59)
Chapter 13 - Ethers, Epoxides, Thiols, and Sulfides
Chapter 13 Slides
13.1 Introduction to and Nomenclature of Ethers (2:41)
13.2 Crown Ethers (2:01)
13.3 Synthesis and Reactions of Ethers (6:34)
13.4 Nomenclature of Epoxides (2:58)
13.5 Synthesis of Epoxides (4:09)
13.6 Ring Opening of Epoxides (4:49)
13.7 Nomenclature, Synthesis, and Reactions of Thiols (4:37)
13.8 Nomenclature, Synthesis, and Reactions of Sulfides (2:51)
13.9 Patterns in Synthesis (8:37)
Chapter 14 - IR Spectroscopy and Mass Spectrometry
Chapter 14 Part 1 Slides - IR Spectroscopy
Chapter 14 Part 2 Slides - Mass Spectrometry
14.1 Introduction to IR spectroscopy
14.2a IR Spectra of Carbonyl Compounds
14.2b The Effect of Conjugation on the Carbonyl Stretching Frequency (5:57)
14.3 Interpreting More IR Spectra (6:45)
14.4 Introduction to Mass Spectrometry (6:19)
14.5 Isotope Effects in Mass Spectrometry (6:29)
14.6a Fragmentation Patterns of Alkanes, Alkenes, and Aromatic Compounds (6:19)
14.6b Fragmentation Patterns for Alkyl Halides, Alcohols, and Amines (4:56)
14.6c Fragmentation Patterns for Ketones and Aldehydes (3:45)
IR Spectroscopy Quiz
Chapter 15 - NMR Spectroscopy
Chapter 15 Slides Part 1 -- The Number of Signals
Chapter 15 Slides Part 2 -- Interpreting NMR
15.1 Introduction to NMR (2:45)
15.2 The Number of Signals in C-13 NMR (4:52)
15.3 The Number of Signals in Proton NMR (10:38)
15.4 Homotopic vs Enantiotopic vs Diastereotopic (10:15)
15.5a The Chemical Shift in C-13 and Proton NMR (8:40)
15.5b The Integration or Area Under the Signal in Proton NMR (1:46)
15.5c The Splitting or Multiplicity in Proton NMR (4:55)
15.6a Interpreting NMR Example 1 (5:10)
15.6b Interpreting NMR Example 2 (7:43)
15.6c Interpreting NMR Example 3 (3:53)
15.6d Structural Determination From All Spectra Example 4 (5:58)
15.6e Structural Determination From All Spectra Example 5 (8:47)
15.7 Complex Splitting (11:42)
NMR Spectroscopy Quiz (25 Questions)
Chapter 16 - Conjugated Pi Systems
Chapter 16 Slides Part 1 - Conjugated Pi Systems
Chapter 16 Slides Part 2 - Pericyclic Reactions
16.1 Introduction to Conjugated Systems and Heats of Hydrogenation (8:19)
16.2a Introduction to Pi Molecular Orbitals - Ethylene (6:56)
16.2b Pi Molecular Orbitals - 1,3-Butadiene (6:16)
16.2c Pi Molecular Orbitals - the Allyl System (5:14)
16.2d Pi Molecular Orbitals - 1,3,5-Hexatriene (5:30)
16.3 UV-Vis Spectroscopy (1:50)
16.4 Addition Reactions to Conjugated Dienes (10:49)
16.5a Introduction to Diels-Alder Reactions (7:42)
16.5b Stereoselectivity and Regioselectivity in Diels-Alder Reactions (11:58)
16.5c Diels-Alder Reactions with Cyclic Dienes (10:02)
16.5d Conservation of Orbital Symmetry in Diels-Alder Reactions (3:40)
16.6 Cycloaddition Reactions (9:38)
16.7 Electrocyclic Reactions (14:19)
16.8 Sigmatropic Rearrangements (6:14)
Chapter 17 - Aromatic Compounds
Chapter 17 Slides
17.1 Nomenclature of Benzenes (9:47)
17.2a Criteria for Aromatic Compounds (5:01)
17.2b Aromatic vs Nonaromatic vs Antiaromatic (15:55)
17.3 The Effects of Aromaticity on SN1 Reactions and Acidity-Basicity (3:59)
17.4 Aromaticity and Molecular Orbital Theory (8:23)
Chapter 18 - Reactions of Aromatic Compounds
Chapter 18 Slides
18.1 Introduction to Aromatic Substitution Reactions (6:27)
18.2a EAS - Bromination and Chlorination (4:37)
18.2b EAS - Sulfonation and Desulfonation (2:24)
18.2c EAS - Nitration (2:55)
18.2d EAS - Friedel-Crafts Alkylation and Acylation (10:35)
18.2e EAS - Activating and Deactivating Groups and Ortho-Para and Meta Directors (12:07)
18.2f EAS - Predicting the Products of EAS Reactions (5:17)
18.3 Catalytic Hydrogenation and the Birch Reduction (2:12)
18.4a - Side-Chain Oxidation with Permanganate or Chromic Acid (1:34)
18.4b - Benzylic Bromination with NBS (1:15)
18.4c - The Clemmensen and Wolff Kishner Reductions (5:11)
18.4d - Side-Chain General Reduction (1:25)
18.5 - Nucleophilic Aromatic Substitution (6:40)
18.6 Patterns in Synthesis (14:18)
Chapter 19 - Ketones and Aldehydes
Chapter 19 Slides
19.1 Nomenclature of Ketones and Aldehydes (5:32)
19.2 Synthesis of Ketones and Aldehydes (3:14)
19.3 Introduction to Nucleophilic Addition Reactions (6:36)
19.4 Hydration (Addition of Water) (3:05)
19.5a Addition of Alcohols (7:15)
19.5b Cyclic Acetals as Protecting Groups (4:25)
19.6a Addition of Primary Amines (Imine Formation) (6:18)
19.6b Addition of Secondary Amines (Enamine Formation) (4:30)
19.6c Mechanism for the Woff Kishner Reduction (4:44)
19.7 Reduction via Thioacetals (1:16)
19.8 Hydride Reduction Reactions (2:42)
19.9a Addition of Acetylide Ions and Grignard Reagents (1:08)
19.9b Addition of HCN (Cyanohydrin Formation) (1:01)
19.9c The Wittig Reaction (5:18)
19.10 Baeyer-Villiger Oxidation (2:51)
19.11 Patterns in Synthesis (12:32)
Chapter 20 - Carboxylic Acids and Acid Derivatives
Chapter 20 Slides
20.1 Introduction to and Physical Properties of Carboyxylic Acids and Acid Derivatives (3:45)
20.2a Nomenclature of Carboxylic Acids (2:24)
20.2b Nomenclature of Acid Halides (0:49)
20.2c Nomenclature of Acid Anhydrides (1:19)
20.2d Nomenclature of Esters (1:44)
20.2e Nomenclature of Amides (1:04)
20.2f Nomenclature of Nitriles (0:43)
20.3 Introduction to Nucleophilic Acyl Substitution (4:07)
20.4 Reaction with Organometallic Reagents (3:27)
20.5 Hydride Reduction (9:45)
20.6 Interconversion of Carboxylic Acids and Derivatives (6:57)
20.7 The Mechanisms of Nucleophilic Acyl Substitution (7:51)
20.8a Synthesis of Acid Halides (3:33)
20.8b Reactions of Acid Halides (3:24)
20.9 Synthesis and Reactions of Acid Anhydrides (2:41)
20.10a Synthesis of Esters (5:59)
20.10b Reactions of Esters (5:06)
20.11 Synthesis and Reactions of Carboxylic Acids (5:51)
21.12 Synthesis and Reactions of Amides (1:53)
20.13 Synthesis and Reactions of Nitriles (3:30)
20.14 Patterns in Synthesis (9:16)
Chapter 21 - Substitution Reactions at the Alpha Carbon
Chapter 21 Slides
21.1 Acidity of the Alpha Hydrogen (8:27)
21.2 General Mechanisms of Alpha Substitution Reactions (1:55)
21.3a Alpha Halogenation (4:02)
21.3b The Haloform Reaction (1:27)
21.3c The HVZ Reaction (1:10)
21.4a Alpha Alkylation (2:25)
21.4b The Stork Synthesis (1:44)
21.5a Introduction to Aldol Reactions (3:39)
21.5b Mechanisms of Aldol Reactions (8:17)
21.5c Mixed Aldol Reactions (4:10)
21.5d Intramolecular Aldol Reactions (2:24)
21.6a Claisen Condensation Reactions (5:31)
21.6b Dieckmann Condensation Reactions (2:12)
21.7a Beta-Decarboxylation (2:20)
21.7b The Malonic Ester Synthesis (3:23)
21.7c The Acetoacetic Ester Synthesis (2:23)
21.8 Michael Reactions (6:55)
21.9 The Robinson Annulation (3:41)
21.10 Patterns in Synthesis (5:33)
Chapter 22 - Amines
Chapter 22 Slides
22.1 Classification of Amines (2:14)
22.2 Nomenclature of Amines (4:15)
22.3 Basicity of Amines (2:17)
22.4a Synthesis of Amines - Reduction (1:56)
22.4b Synthesis of Amines - Hofmann Rearrangement (3:07)
22.4c Synthesis of Amines - Curtius Rearrangement and Schmidt Reaction (2:06)
22.4d Synthesis of Amines - Gabriel Synthesis (4:07)
22.4e Synthesis of Amines - Reductive Amination (1:49)
22.5 Acylation (0:57)
22.6 Hofmann Elimination (3:59)
22.7 Cope Elimination (1:03)
22.8a Reaction with Nitrous Acid and the Sandmeyer Reactions (1:59)
22.8b Azo Coupling (1:16)
22.9 EAS Reactions with Nitrogen Heterocycles (2:17)
22.10 Patterns in Synthesis (9:56)
11.4c Common Patterns in Synthesis Part 3 (5:20)
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