Summary of Organic Reactions
Chapter 1 - Electrons, Bonding, and Molecular Properties
Chapter 2 - Molecular Representations and Resonance
Chapter 3 - Acids and Bases
Chapter 4 - Alkanes
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Chapter 4 Part 1 Slides - Nomenclature of Alkanes
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Chapter 4 Part 2 Slides - Constitutional Isomers and Conformations of Alkanes
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4.1a Nomenclature of Alkanes (15:32)
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4.1b Nomenclature of Cycloalkanes (8:20)
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4.1c Systematic Nomenclature of Complex Substituents (4:22)
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4.1d Common Names of Complex Substituents (7:53)
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4.1e Nomenclature of Bicyclic Compounds (5:44)
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4.2 Drawing Constitutional Isomers (6:18)
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4.3 Newman Projections (8:20)
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4.4 Cycloalkanes and Cyclohexane Chair Conformations (22:38)
Chapter 5 - Isomers and Stereochemistry
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Chapter 5 Slides
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5.1 Overview of Isomerism (7:24)
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5.2 Chiral Centers and Chirality (5:23)
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5.3 Absolute Configurations - Assigning R and S (14:47)
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5.4 Molecules with Multiple Chiral Centers (15:15)
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5.5 Fischer Projections (6:13)
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5.6 Determining the Relationship Between a Pair of Molecules (6:43)
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5.7 Amine Inversion and Chiral Molecules Without Chiral Centers (5:23)
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5.8 Optical Activity (7:40)
Chapter 6 - Introduction to Organic Reactions and Mechanisms
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Chapter 6 Slides
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6.1 Reaction Enthalpies and Bond Dissociation Energies (6:12)
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6.2 Entropy, Gibbs Free Energy, and the Equilibrium Constant (9:44)
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6.3 The Kinetics of Organic Reactions (4:41)
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6.4 Nucleophiles, Electrophiles, and Intermediates (5:44)
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6.5 Reaction Mechanisms and Curved Arrow Pushing (7:11)
Chapter 7 - Substitution and Elimination Reactions of Alkyl Halides
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Chapter 7 Part 1 - Slides
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Chapter 7 Part 2 Slides
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7.1a Introduction to SN2 Reactions (9:14)
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7.1b Factors Affecting SN2 Reactions (11:40)
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7.2a Introduction to SN1 Reactions (4:45)
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7.2b Carbocation Rearrangements in SN1 Reactions (8:30)
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7.2c Racemization in SN1 Reactions (1:37)
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7.2d Factors Affecting SN1 Reactions (4:51)
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7.3 Unreactivity of Vinyl and Aryl Halides (2:09)
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7.4 Predicting the Products of Substitution Reactions (18:05)
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7.5 Nomenclature of Alkenes (15:18)
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7.6 Stability of Alkenes (2:17)
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7.7a Introduction to E2 Elimination Reactions (6:42)
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7.7b Exceptions to Zaitsev's Rule for E2 Reactions (8:37)
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7.7c The Stereospecificity of E2 Reactions -- Anti-periplanar (10:41)
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7.8 Introduction to E1 Elimination Reactions (4:54)
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7.9 Predicting the Products of Elimination Reactions (10:02)
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7.10 Distinguishing Between Substitution and Elimination Reactions (16:53)
Chapter 8 - Addition Reactions to Alkenes
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Chapter 8 Slides
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8.1 Introduction to Alkene Addition Reactions (4:00)
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8.2 Hydrohalogenation (5:08)
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8.3a Hydration -- Acid-Catalyzed Hydration (3:25)
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8.3b Hydration -- Oxymercuration-Demercuration (6:07)
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8.3c Hydration -- Hydroboration-Oxidation (4:14)
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8.4a Acid-Catalyzed Addition of an Alcohol (2:25)
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8.4b Alkoxymercuration-Demercuration (1:15)
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8.5 Catalytic Hydrogenation (3:17)
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8.6a Halogenation (3:55)
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8.6b Halohydrin Formation (3:20)
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Halogenation Quiz (7 Questions)
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8.7a Anti-Dihydroxylation (4:12)
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8.7b Syn-Dihydroxylation (2:40)
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8.8 Predicting the Products of Alkene Addition Reactions (10:18)
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8.9 Oxidative Cleavage -- Ozonolysis and Permanganate Cleavage (4:49)
Chapter 9 - Alkynes
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Chapter 9 Slides
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9.1 Nomenclature of Alkynes (3:49)
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9.2 Acidity of Alkynes (2:32)
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9.3 Preparation of Alkynes (3:37)
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9.4 Reduction of Alkynes (6:01)
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9.5 Introduction to Addition Reactions of Alkynes (2:19)
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9.6 Hydrohalogenation (3:17)
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9.7 Halogenation (1:35)
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9.8a Acid-Catalyzed Hydration (4:10)
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9.8b Hydroboration-Oxidation (5:07)
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9.8c Keto-Enol Tautomerization (3:58)
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9.9 Ozonolysis (1:21)
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9.10 Alkylation of Acetylide Ions (2:21)
Chapter 10 - Radical Reactions
Chapter 11 - Synthesis
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Chapter 11 Slides
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11.1 Functional Group Conversions (4:19)
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11.2 Increasing the Length of the Carbon Skeleton (8:06)
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11.3 Decreasing the Length of the Carbon Chain or Opening a Ring (2:43)
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11.4a Common Patterns in Synthesis Part 1 (5:25)
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11.4b Common Patterns in Synthesis Part 2 (8:51)
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11.4c Common Patterns in Synthesis Part 3 (5:20)
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11.4d Common Patterns in Synthesis Part 4 (9:46)
Chapter 12 - Alcohols
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Chapter 12 Slides
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12.1 Properties and Nomenclature of Alcohols (4:47)
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12.2 Acidity of Alcohols and Phenols (13:07)
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12.3a Synthesis of Alcohols; Reduction of Ketones and Aldehydes (8:06)
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12.3b Synthesis of Alcohols; Grignard Addition (8:19)
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12.4 Protecting Alcohols (5:44)
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12.5a Reaction with HCl, HBr, and HI (4:22)
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12.5b Substitution with PBr3 and SOCl2 (5:05)
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12.5c Formation of Tosylate Esters (3:37)
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12.6 Elimination (Dehydration) (3:14)
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12.7 Oxidation with Chromic Acid and PCC (9:25)
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12.8 Patterns in Synthesis (9:00) (8:59)
Chapter 13 - Ethers, Epoxides, Thiols, and Sulfides
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Chapter 13 Slides
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13.1 Introduction to and Nomenclature of Ethers (2:42)
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13.2 Crown Ethers (2:03)
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13.3 Synthesis and Reactions of Ethers (6:35)
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13.4 Nomenclature of Epoxides (3:00)
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13.5 Synthesis of Epoxides (4:10)
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13.6 Ring Opening of Epoxides (4:50)
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13.7 Nomenclature, Synthesis, and Reactions of Thiols (4:38)
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13.8 Nomenclature, Synthesis, and Reactions of Sulfides (2:52)
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13.9 Patterns in Synthesis (8:38) (8:37)
Chapter 14 - IR Spectroscopy and Mass Spectrometry
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Chapter 14 Part 1 Slides - IR Spectroscopy
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Chapter 14 Part 2 Slides - Mass Spectrometry
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14.1 Introduction to IR spectroscopy (10:57)
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14.2a IR Spectra of Carbonyl Compounds (6:27)
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14.2b The Effect of Conjugation on the Carbonyl Stretching Frequency (5:58)
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14.3 Interpreting More IR Spectra (6:45)
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14.4 Introduction to Mass Spectrometry (6:19)
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14.5 Isotope Effects in Mass Spectrometry (6:30)
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14.6a Fragmentation Patterns of Alkanes, Alkenes, and Aromatic Compounds (6:20)
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14.6b Fragmentation Patterns for Alkyl Halides, Alcohols, and Amines (4:56)
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14.6c Fragmentation Patterns for Ketones and Aldehydes (3:45)
Chapter 15 - NMR Spectroscopy
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Chapter 15 Slides Part 1 -- The Number of Signals
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Chapter 15 Slides Part 2 -- Interpreting NMR
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15.1 Introduction to NMR (2:46)
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15.2 The Number of Signals in C-13 NMR (4:53)
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15.3 The Number of Signals in Proton NMR (10:38)
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15.4 Homotopic vs Enantiotopic vs Diastereotopic (10:16)
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15.5a The Chemical Shift in C-13 and Proton NMR (8:41)
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15.5b The Integration or Area Under the Signal in Proton NMR (1:47)
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15.5c The Splitting or Multiplicity in Proton NMR (4:55)
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15.6a Interpreting NMR Example 1 (5:10)
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15.6b Interpreting NMR Example 2 (7:43)
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15.6c Interpreting NMR Example 3 (3:54)
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15.6d Structural Determination From All Spectra Example 4 (5:58)
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15.6e Structural Determination From All Spectra Example 5 (8:48)
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15.7 Complex Splitting (11:42)
Chapter 16 - Conjugated Pi Systems
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Chapter 16 Slides Part 1 - Conjugated Pi Systems
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Chapter 16 Slides Part 2 - Pericyclic Reactions
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16.1 Introduction to Conjugated Systems and Heats of Hydrogenation (8:20)
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16.2a Introduction to Pi Molecular Orbitals - Ethylene (6:57)
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16.2b Pi Molecular Orbitals - 1,3-Butadiene (6:17)
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16.2c Pi Molecular Orbitals - the Allyl System (5:15)
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16.2d Pi Molecular Orbitals - 1,3,5-Hexatriene (5:31)
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16.3 UV-Vis Spectroscopy (1:51)
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16.4 Addition Reactions to Conjugated Dienes (10:51)
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16.5a Introduction to Diels-Alder Reactions (7:43)
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16.5b Stereoselectivity and Regioselectivity in Diels-Alder Reactions (11:59)
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16.5c Diels-Alder Reactions with Cyclic Dienes (10:03)
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16.5d Conservation of Orbital Symmetry in Diels-Alder Reactions (3:41)
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16.6 Cycloaddition Reactions (9:39)
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16.7 Electrocyclic Reactions (14:20)
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16.8 Sigmatropic Rearrangements (6:15)
Chapter 17 - Aromatic Compounds
Chapter 18 - Reactions of Aromatic Compounds
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Chapter 18 Slides
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18.1 Introduction to Aromatic Substitution Reactions (6:28)
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18.2a EAS - Bromination and Chlorination (4:38)
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18.2b EAS - Sulfonation and Desulfonation (2:26)
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18.2c EAS - Nitration (2:56)
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18.2d EAS - Friedel-Crafts Alkylation and Acylation (10:36)
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18.2e EAS - Activating and Deactivating Groups and Ortho-Para and Meta Directors (12:08)
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18.2f EAS - Predicting the Products of EAS Reactions (5:18)
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18.3 Catalytic Hydrogenation and the Birch Reduction (2:13)
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18.4a - Side-Chain Oxidation with Permanganate or Chromic Acid (1:35)
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18.4b - Benzylic Bromination with NBS (1:16)
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18.4c - The Clemmensen and Wolff Kishner Reductions (5:12)
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18.4d - Side-Chain General Reduction (1:26)
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18.5 - Nucleophilic Aromatic Substitution (6:41)
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18.6 Patterns in Synthesis (14:18) (14:18)
Chapter 19 - Ketones and Aldehydes
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Chapter 19 Slides
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19.1 Nomenclature of Ketones and Aldehydes (5:33)
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19.2 Synthesis of Ketones and Aldehydes (3:15)
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19.3 Introduction to Nucleophilic Addition Reactions (6:37)
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19.4 Hydration (Addition of Water) (3:06)
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19.5a Addition of Alcohols (7:16)
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19.5b Cyclic Acetals as Protecting Groups (4:26)
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19.6a Addition of Primary Amines (Imine Formation) (6:19)
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19.6b Addition of Secondary Amines (Enamine Formation) (4:31)
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19.6c Mechanism for the Woff Kishner Reduction (4:45)
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19.7 Reduction via Thioacetals (1:17)
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19.8 Hydride Reduction Reactions (2:43)
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19.9a Addition of Acetylide Ions and Grignard Reagents (1:09)
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19.9b Addition of HCN (Cyanohydrin Formation) (1:02)
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19.9c The Wittig Reaction (5:19)
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19.10 Baeyer-Villiger Oxidation (2:52)
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19.11 Patterns in Synthesis (12:32) (12:32)
Chapter 20 - Carboxylic Acids and Acid Derivatives
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Chapter 20 Slides
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20.1 Introduction to and Physical Properties of Carboyxylic Acids and Acid Derivatives (3:47)
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20.2a Nomenclature of Carboxylic Acids (2:25)
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20.2b Nomenclature of Acid Halides (0:50)
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20.2c Nomenclature of Acid Anhydrides (1:20)
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20.2d Nomenclature of Esters (1:46)
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20.2e Nomenclature of Amides (1:05)
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20.2f Nomenclature of Nitriles (0:44)
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20.3 Introduction to Nucleophilic Acyl Substitution (4:08)
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20.4 Reaction with Organometallic Reagents (3:28)
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20.5 Hydride Reduction (9:46)
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20.6 Interconversion of Carboxylic Acids and Derivatives (6:58)
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20.7 The Mechanisms of Nucleophilic Acyl Substitution (7:52)
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20.8a Synthesis of Acid Halides (3:34)
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20.8b Reactions of Acid Halides (3:25)
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20.9 Synthesis and Reactions of Acid Anhydrides (2:42)
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20.10a Synthesis of Esters (6:00)
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20.10b Reactions of Esters (5:07)
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20.11 Synthesis and Reactions of Carboxylic Acids (5:52)
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20.12 Synthesis and Reactions of Amides (1:54)
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20.13 Synthesis and Reactions of Nitriles (3:32)
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20.14 Patterns in Synthesis (9:16) (9:16)
Chapter 21 - Substitution Reactions at the Alpha Carbon
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Chapter 21 Slides
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21.1 Acidity of the Alpha Hydrogen (8:28)
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21.2 General Mechanisms of Alpha Substitution Reactions (1:57)
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21.3a Alpha Halogenation (4:03)
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21.3b The Haloform Reaction (1:28)
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21.3c The HVZ Reaction (1:11)
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21.4a Alpha Alkylation (2:26)
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21.4b The Stork Synthesis (1:45)
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21.5a Introduction to Aldol Reactions (3:40)
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21.5b Mechanisms of Aldol Reactions (8:19)
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21.5c Mixed Aldol Reactions (4:11)
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21.5d Intramolecular Aldol Reactions (2:25)
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21.6a Claisen Condensation Reactions (5:32)
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21.6b Dieckmann Condensation Reactions (2:13)
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21.7a Beta-Decarboxylation (2:21)
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21.7b The Malonic Ester Synthesis (3:24)
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21.7c The Acetoacetic Ester Synthesis (2:24)
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21.8 Michael Reactions (6:56)
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21.9 The Robinson Annulation (3:42)
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21.10 Patterns in Synthesis (5:34) (5:33)
Chapter 22 - Amines
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Chapter 22 Slides
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22.1 Classification of Amines (2:16)
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22.2 Nomenclature of Amines (4:16)
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22.3 Basicity of Amines (2:18)
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22.4a Synthesis of Amines - Reduction (1:57)
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22.4b Synthesis of Amines - Hofmann Rearrangement (3:08)
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22.4c Synthesis of Amines - Curtius Rearrangement and Schmidt Reaction (2:07)
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22.4d Synthesis of Amines - Gabriel Synthesis (4:08)
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22.4e Synthesis of Amines - Reductive Amination (1:50)
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22.5 Acylation (0:58)
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22.6 Hofmann Elimination (4:00)
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22.7 Cope Elimination (1:04)
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22.8a Reaction with Nitrous Acid and the Sandmeyer Reactions (2:00)
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22.8b Azo Coupling (1:17)
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22.9 EAS Reactions with Nitrogen Heterocycles (2:18)
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22.10 Patterns in Synthesis (9:57) (9:56)
