| Arenes and Aromaticity |
| Benzene |
| Kekulé and the Structure of Benzene |
| A Resonance Picture of Bonding in Benzene |
| The Stability of Benzene |
| An Orbital Hybridization View of Bonding in Benzene |
| The Pi Molecular Orbitals of Benzene |
| Substituted Derivatives of Benzene and Their Nomenclature |
| Polycyclic Aromatic Hydrocarbons |
| Physical Properties of Arenes |
| Carbon Clusters, Fullerenes, and Nanotubes |
| Reactions of Arenes: A Preview |
| The Birch Reduction |
| Free-Radical Halogenation of Alkylbenzenes |
| Oxidation of Alkylbenzenes |
| Sn1 Reactions of Benzylic Halides |
| Sn2 Reactions of Benzylic Halides |
| Preparation of Alkenylbenzenes |
| Addition Reactions of Alkenylbenzenes |
| Polymerization of Styrene |
| Cyclobutadiene and Cyclooctatetraene |
| Hückel's Rule 448 |
| Annulenes |
| Aromatic Ions |
| Heterocyclic Aromatic Compounds |
| Heterocyclic Aromatic Compounds and Hückel's Rule |
| Reactions of Arenes: Electrophilic Aromatic Substitution |
| Representative Electrophilic Aromatic Substitution Reactions of Benzene |
| Mechanistic Principles of Electrophilic Aromatic Substitution |
| Nitration of Benzene |
| Sulfonation of Benzene |
| Halogenation of Benzene |
| Friedel-Crafts Alkylation of Benzene |
| Friedel-Crafts Acylation of Benzene |
| Synthesis of Alkylbenzenes by Acylation-Reduction |
| Rate and Regioselectivity in Electrophilic Aromatic Substitution |
| Rate and Regioselectivity in the Nitration of Toluene |
| Rate and Regioselectivity in the Nitration of (Trifluoromethyl) benzene |
| Substituent Effects in Electrophilic Aromatic Substitution: Activating Substituents |
| Substituent Effects in Electrophilic Aromatic Substitution: Strongly Deactivating Substituents |
| Substituent Effects in Electrophilic Aromatic Substitution: Halogens |
| Multiple Substituent Effects |
| Regioselective Synthesis of Disubstituted Aromatic Compounds |
| Substitution in Naphthalene |
| Substitution in Heterocyclic Aromatic Compounds |
| Spectroscopy |
| Principles of Molecular Spectroscopy: Electromagnetic Radiation |
| Principles of Molecular Spectroscopy: Quantized Energy States |
| Introduction to 1 H NMR Spectroscopy |
| Nuclear Shielding and 1 H Chemical Shifts |
| ffects of Molecular Structure on 1 H Chemical Shifts |
| Ring Currents: Aromatic and Antiaromatic |
| Interpreting 1 H NMR Spectra |
| Spin-Spin Splitting in 1 H NMR Spectroscopy |
| Splitting Patterns: The Ethyl Group |
| Splitting Patterns: The Isopropyl Group |
| Splitting Patterns: Pairs of Doublets |
| Complex Splitting Patterns |
1 H NMR Spectra of Alcohols
Magnetic Resonance Imaging (MRI) |
| NMR and Conformations |
| 13 C NMR Spectroscopy |
| 13 C Chemical Shifts |
| 13 C NMR and Peak Intensities |
| 13 C 1 H Coupling |
| Using DEPT to Count Hydrogens Attached to 13 C |
| 2D NMR: COSY and HETCOR |
| Introduction to Infrared Spectroscopy |
| Infrared Spectra |
| Characteristic Absorption Frequencies |
| Ultraviolet-Visible (UV-VIS) Spectroscopy |
| Mass Spectrometry |
| Molecular Formula as a Clue to Structure |
| Organometallic Compounds |
| Organometallic Nomenclature |
| Carbon-Metal Bonds in Organometallic Compounds |
| Preparation of Organolithium Compounds |
| Preparation of Organomagnesium Compounds: Grignard Reagents |
| Organolithium and Organomagnesium Compounds as Brønsted Bases |
| Synthesis of Alcohols Using Grignard Reagents |
| Synthesis of Alcohols Using Organolithium Reagents |
| Synthesis of Acetylenic Alcohols |
| Retrosynthetic Analysis |
| Preparation of Tertiary Alcohols from Esters and Grignard Reagents |
| Alkane Synthesis Using Organocopper Reagents |
| An Organozinc Reagent for Cyclopropane Synthesis |
| Carbenes and Carbenoids |
| Transition-Metal Organometallic Compounds |
| An Organometallic Compound That Occurs Naturally: Coenzyme |
| Olefin Metathesis |
| Ziegler-Natta Catalysis of Alkene Polymerization |
| Alcohols, Diols, and Thiols |
| Sources of Alcohols |
| Preparation of Alcohols by Reduction of Aldehydes and Ketones |
| Preparation of Alcohols by Reduction of Carboxylic Acids and Esters |
| Preparation of Alcohols from Epoxides |
| Preparation of Diols |
| Reactions of Alcohols: A Review and a Preview |
| Conversion of Alcohols to Ethers |
| Esterification |
| Esters of Inorganic Acids |
| Oxidation of Alcohols |
| Biological Oxidation of Alcohols |
| Economic and Environmental Factors in Organic Synthesis |
| Oxidative Cleavage of Vicinal Diols |
| Thiols |
| Spectroscopic Analysis of Alcohols and Thiols |
| Ethers, Epoxides, and Sulfides |
| Nomenclature of Ethers, Epoxides, and Sulfides |
Structure and Bonding in Ethers and Epoxides
Physical Properties of Ethers
Crown Ethers |
| Preparation of Ethers |
| Polyether Antibiotics |
| The Williamson Ether Synthesis |
| Reactions of Ethers: A Review and a Preview |
| Acid-Catalyzed Cleavage of Ethers |
| Preparation of Epoxides: A Review and a Preview |
| Conversion of Vicinal Halohydrins to Epoxides |
| Reactions of Epoxides: A Review and a Preview |
| Nucleophilic Ring Opening of Epoxides |
| Acid-Catalyzed Ring Opening of Epoxides |
| Epoxides in Biological Processes |
| Preparation of Sulfides |
| Oxidation of Sulfides: Sulfoxides and Sulfones |
| Alkylation of Sulfides: Sulfonium Salts |
| Spectroscopic Analysis of Ethers, Epoxides, and Sulfides |
| Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group |
| Nomenclature |
| Structure and Bonding: The Carbonyl Group |
| Physical Properties |
| Sources of Aldehydes and Ketones |
| Reactions of Aldehydes and Ketones: A Review and a Preview |
| Principles of Nucleophilic Addition: Hydration of Aldehydes and Ketones |
| Cyanohydrin Formation |
| Acetal Formation |
| Acetals as Protecting Groups |
| Reaction with Primary Amines: Imines |
| Imines in Biological Chemistry |
| Reaction with Secondary Amines: Enamines |
| The Wittig Reaction |
| Planning an Alkene Synthesis via the Wittig Reaction |
| Stereoselective Addition to Carbonyl Groups |
| Oxidation of Aldehydes |
| Baeyer-Villiger Oxidation of Ketones |
| Spectroscopic Analysis of Aldehydes and Ketones |
| Enols and Enolates |
| The -Hydrogen and Its pKa |
| The Aldol Condensation |
| Mixed Aldol Condensations |
| Alkylation of Enolate Ions |
| Enolization and Enol Content |
| Stabilized Enols |
| Halogenation of Aldehydes and Ketones |
| Mechanism of Halogenation of Aldehydes and Ketones |
| The Haloform Reaction |
| Some Chemical and Stereochemical Consequences of Enolization |
| The Haloform Reaction and the Biosynthesis of Trihalomethanes |
| Effects of Conjugation in ,-Unsaturated Aldehydes and Ketones |
| Conjugate Addition to ,-Unsaturated Carbonyl Compounds |
| Addition of Carbanions to ,-Unsaturated Ketones: The Michael Reaction |
| Conjugate Addition of Organocopper Reagents to ,-Unsaturated Carbonyl Compounds |
| Carboxylic Acids |
| Carboxylic Acid Nomenclature |
| Structure and Bonding |
| Physical Properties |
| Acidity of Carboxylic Acids |
| Salts of Carboxylic Acids |
| Substituents and Acid Strength |
| Ionization of Substituted Benzoic Acids |
| Dicarboxylic Acids |
| Carbonic Acid |
| Sources of Carboxylic Acids |
| Synthesis of Carboxylic Acids by the Carboxylation of Grignard Reagents |
| Synthesis of Carboxylic Acids by the Preparation and Hydrolysis of Nitriles |
| Reactions of Carboxylic Acids: A Review and a Preview |
| Mechanism of Acid-Catalyzed Esterification |
| Intramolecular Ester Formation: Lactones |
| Alpha Halogenation of Carboxylic Acids: The Hell-Volhard-Zelinsky Reaction |
| Decarboxylation of Malonic Acid and Related Compounds |
| Spectroscopic Analysis of Carboxylic Acids |
