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| Preface to the Second Edition | |
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| Preface to First Edition | |
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| Introduction: Molecular Structure and Reactivity | |
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| How to Write Lewis Structures and Calculate Formal Charges | |
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| Determining the Number of Bonds | |
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| Determining the Number of Rings and/or [pi] Bonds (Degree of Unsaturation | |
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| Drawing the Lewis Structure | |
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| Formal Charge | |
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| Representations of Organic Compounds | |
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| Geometry and Hybridization | |
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| Electronegativities and Dipoles | |
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| Resonance Structures | |
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| Drawing Resonance Structures | |
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| Rules for Resonance Structures | |
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| Aromaticity and Antiaromaticity | |
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| Aromatic Carbocycles | |
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| Aromatic Heterocycles | |
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| Antiaromaticity | |
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| Tautomers and Equilibrium | |
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| Acidity and Basicity | |
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| Nucleophiles and Electrophiles | |
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| Nucleophilicity | |
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| Substrate | |
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| Solvent | |
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| General Principles for Writing Reaction Mechanisms | |
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| Balancing Equations | |
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| Using Arrows to Show Moving Electrons | |
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| Mechanisms in Acidic and Basic Media | |
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| Electron-Rich Species: Bases or Nucleophiles? | |
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| Trimolecular Steps | |
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| Stability of Intermediates | |
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| Driving Forces for Reactions | |
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| Leaving Groups | |
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| Formation of a Small Stable Molecule | |
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| Structural Relationships between Starting Materials and Products | |
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| Solvent Effects | |
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| A Last Word | |
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| Reactions of Nucleophiles and Bases | |
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| Nucleophilic Substitution | |
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| The S[subscript N]2 Reaction | |
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| Nucleophilic Substitution at Aliphatic sp[superscript 2] Carbon (Carbonyl Groups) | |
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| Nucleophilic Substitution at Aromatic Carbons | |
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| Eliminations at Saturated Carbon | |
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| E2 Elimination | |
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| Ei Elimination | |
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| Nucleophilic Addition to Carbonyl Compounds | |
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| Addition of Organometallic Reagents | |
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| Reaction of Nitrogen-Containing Nucleophiles with Aldehydes and Ketones | |
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| Reactions of Carbon Nucleophiles with Carbonyl Compounds | |
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| Base-Promoted Rearrangements | |
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| The Favorskii Rearrangement | |
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| The Benzilic Acid Rearrangement | |
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| Additional Mechanisms in Basic Media | |
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| Reactions Involving Acids and Other Electrophiles | |
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| Stability of Carbocations | |
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| Formation of Carbocations | |
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| Ionization | |
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| Addition of an Electrophile to a [pi] Bond | |
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| Reaction of an Alkyl Halide with a Lewis Acid | |
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| The Fate of Carbocations | |
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| Rearrangement of Carbocations | |
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| The Dienone-Phenol Rearrangement | |
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| The Pinacol Rearrangement | |
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| Electrophilic Addition | |
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| Regiospecificity | |
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| Stereochemistry | |
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| Acid-Catalyzed Reactions of Carbonyl Compounds | |
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| Hydrolysis of Carboxylic Acid Derivatives | |
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| Hydrolysis and Formation of Acetals and Orthoesters | |
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| 1,4-Addition | |
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| Electrophilic Aromatic Substitution | |
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| Carbenes | |
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| Singlet and Triplet Carbenes | |
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| Formation of Carbenes | |
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| Reactions of Carbenes | |
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| Electrophilic Heteroatoms | |
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| Electron-Deficient Nitrogen | |
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| Rearrangements Involving Electrophilic Nitrogen | |
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| Rearrangement Involving Electron-Deficient Oxygen | |
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| Radicals and Radical Anions | |
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| Introduction | |
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| Formation of Radicals | |
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| Homolytic Bond Cleavage | |
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| Hydrogen Abstraction from Organic Molecules | |
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| Organic Radicals Derived from Functional Groups | |
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| Radical Chain Processes | |
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| Radical Inhibitors | |
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| Determining the Thermodynamic Feasibility of Radical Reactions | |
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| Addition of Radicals | |
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| Intermolecular Radical Addition | |
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| Intramolecular Radical Addition: Radical Cyclization Reactions | |
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| Fragmentation Reactions | |
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| Loss of CO[subscript 2] | |
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| Loss of a Ketone | |
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| Loss of N[subscript 2] | |
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| Loss of CO | |
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| Rearrangement of Radicals | |
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| The S[subscript RN] 1 Reaction | |
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| The Birch Reduction | |
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| A Radical Mechanism for the Rearrangement of Some Anions | |
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| Pericyclic Reactions | |
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| Introduction | |
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| Types of Pericyclic Reactions | |
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| Theories of Pericyclic Reactions | |
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| Electrocyclic Reactions | |
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| Selection Rules for Electrocyclic Reactions | |
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| Stereochemistry of Electrocyclic Reactions (Conrotatory and Disrotatory Processes) | |
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| Electrocyclic Reactions of Charged Species (Cyclopropyl Cations) | |
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| Cycloadditions | |
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| Terminology of Cycloadditions | |
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| Selection Rules for Cycloadditions | |
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| Secondary Interactions | |
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| Cycloadditions of Charged Species | |
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| Sigmatropic Rearrangements | |
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| Terminology | |
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| Selection Rules for Sigmatropic Rearrangements | |
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| The Ene Reaction | |
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| A Molecular Orbital View of Pericyclic Processes | |
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| Orbitals | |
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| Molecular Orbitals | |
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| Generating and Analyzing [pi] Molecular Orbitals | |
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| HOMOs and LUMOs | |
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| Correlation Diagrams | |
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| Frontier Orbitals | |
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| Additional Problems | |
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| Lewis Structures of Common Functional Groups | |
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| Symbols and Abbreviations Used in Chemical Notation | |
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| Relative Acidities of Common Organic and Inorganic Substances | |
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| Index | |