| Chemical Bonding and Structure / Chapter 1.： |
| Valence Bond Description of Chemical Bonding / 1.1.： |
| Orbital Hybridization / 1.1.1.： |
| Resonance / 1.1.2.： |
| Bond Energy, Polarity, and Polarizability / 1.2.： |
| Bond Energies / 1.2.1.： |
| Electronegativity and Polarity / 1.2.2.： |
| Polarizability--Hardness and Softness / 1.2.3.： |
| Molecular Orbital Theory and Methods / 1.3.： |
| Huckel Molecular Orbital Theory / 1.4.： |
| Qualitative Application of Molecular Orbital Theory / 1.5.： |
| Application of Molecular Orbital Theory to Reactivity / 1.6.： |
| Interactions between [sigma] and [pi] Systems--Hyperconjugation / 1.7.： |
| Other Quantitative Descriptions of Molecular Structure / 1.8.： |
| Atoms in Molecules / 1.8.1.： |
| Electron Density Functionals / 1.8.2.： |
| Modern Valence Bond Approaches / 1.8.3.： |
| General References |
| Problems |
| Principles of Stereochemistry / Chapter 2.： |
| Enantiomeric Relationships / 2.1.： |
| Diastereomeric Relationships / 2.2.： |
| Stereochemistry of Reactions / 2.3.： |
| Prochiral Relationships / 2.4.： |
| Conformational, Steric, and Stereoelectronic Effects / Chapter 3.： |
| Strain and Molecular Mechanics / 3.1.： |
| Conformations of Acyclic Molecules / 3.2.： |
| Conformations of Cyclohexane Derivatives / 3.3.： |
| Carbocyclic Rings Other Than Six-Membered / 3.4.： |
| The Effect of Heteroatoms on Conformational Equilibria / 3.5.： |
| The Anomeric Effect / 3.6.： |
| Conformational Effects on Reactivity / 3.7.： |
| Angle Strain and Its Effect on Reactivity / 3.8.： |
| Relationships between Ring Size and Rate of Cyclization / 3.9.： |
| Torsional and Stereoelectronic Effects on Reactivity / 3.10.： |
| Study and Description of Organic Reaction Mechanismns / Chapter 4.： |
| Thermodynamic Data / 4.1.： |
| Kinetic Data / 4.2.： |
| Substituent Effects and Linear Free-Energy Relationships / 4.3.： |
| Basic Mechanistic Concepts: Kinetic versus Thermodynamic Control, Hammond's Postulate, the Curtin-Hammett Principle / 4.4.： |
| Kinetic versus Thermodynamic Control / 4.4.1.： |
| Hammond's Postulate / 4.4.2.： |
| The Curtin-Hammett Principle / 4.4.3.： |
| Isotope Effects / 4.5.： |
| Isotopes in Labeling Experiments / 4.6.： |
| Characterization of Reaction Intermediates / 4.7.： |
| Catalysis by Bronsted Acids and Bases / 4.8.： |
| Lewis Acid Catalysis / 4.9.： |
| Solvent Effects / 4.10.： |
| Substituent Effects in the Gas Phase / 4.11.： |
| Stereochemistry / 4.12.： |
| Conclusion / 4.13.： |
| Nucleophilic Substitution / Chapter 5.： |
| The Limiting Cases--Substitution by the Ionization (S[subscript N]1) Mechanism / 5.1.： |
| The Limiting Cases--Substitution by the Direct Displacement (S[subscript N]2) Mechanism / 5.2.： |
| Detailed Mechanistic Description and Borderline Mechanisms / 5.3.： |
| Carbocations / 5.4.： |
| Nucleophilicity and Solvent Effects / 5.5.： |
| Leaving-Group Effects / 5.6.： |
| Steric and Strain Effects on Substitution and Ionization Rates / 5.7.： |
| Effects of Conjugation on Reactivity / 5.8.： |
| Stereochemistry of Nucleophilic Substitution / 5.9.： |
| Neighboring-Group Participation / 5.10.： |
| Mechanism of Rearrangements of Carbocations / 5.11.： |
| The Norbornyl Cation and Other Nonclassical Carbocations / 5.12.： |
| Polar Addition and Elimination Reactions / Chapter 6.： |
| Addition of Hydrogen Halides to Alkenes / 6.1.： |
| Acid-Catalyzed Hydration and Related Addition Reactions / 6.2.： |
| Addition of Halogens / 6.3.： |
| Electrophilic Additions Involving Metal Ions / 6.4.： |
| Additions to Alkynes and Allenes / 6.5.： |
| The E2, E1, and E1cb Mechanisms / 6.6.： |
| Regiochemistry of Elimination Reactions / 6.7.： |
| Stereochemistry of E2 Elimination Reactions / 6.8.： |
| Dehydration of Alcohols / 6.9.： |
| Eliminations Not Involving C--H Bonds / 6.10.： |
| Carbanions and Other Nucleophilic Carbon Species / Chapter 7.： |
| Acidity of Hydrocarbons / 7.1.： |
| Carbanions Stabilized by Functional Groups / 7.2.： |
| Enols and Enamines / 7.3.： |
| Carbanions as Nucleophiles in S[subscript N]2 Reactions / 7.4.： |
| Reactions of Carbonyl Compounds / Chapter 8.： |
| Hydration and Addition of Alcohols to Aldehydes and Ketones / 8.1.： |
| Addition-Elimination Reactions of Ketones and Aldehydes / 8.2.： |
| Addition of Carbon Nucleophiles to Carbonyl Groups / 8.3.： |
| Reactivity of Carbonyl Compounds toward Addition / 8.4.： |
| Ester Hydrolysis / 8.5.： |
| Aminolysis of Esters / 8.6.： |
| Amide Hydrolysis / 8.7.： |
| Acylation of Nucleophilic Oxygen and nitrogen Groups / 8.8.： |
| Intramolecular Catalysis / 8.9.： |
| Aromaticity / Chapter 9.： |
| The Concept of Aromaticity / 9.1.： |
| The Annulenes / 9.2.： |
| Aromaticity in Charged Rings / 9.3.： |
| Homoaromaticity / 9.4.： |
| Fused-Ring Systems / 9.5.： |
| Heterocyclic Rings / 9.6.： |
| Aromatic Substitution / Chapter 10.： |
| Electrophilic Aromatic Substitution Reactions / 10.1.： |
| Structure-Reactivity Relationships / 10.2.： |
| Reactivity of Polycyclic and Heteroaromatic Compounds / 10.3.： |
| Specific Substitution Mechanisms / 10.4.： |
| Nitration / 10.4.1.： |
| Halogenation / 10.4.2.： |
| Protonation and Hydrogen Exchange / 10.4.3.： |
| Friedel-Crafts Alkylation and Related Reactions / 10.4.4.： |
| Friedel-Crafts Acylation and Related Reactions / 10.4.5.： |
| Coupling with Diazonium Compounds / 10.4.6.： |
| Substitution of Groups Other Than Hydrogen / 10.4.7.： |
| Nucleophilic Aromatic Substitution by the Addition-Elimination Mechanism / 10.5.： |
| Nucleophilic Aromatic Substitution by the Elimination-Addition Mechanism / 10.6.： |
| Concerted Pericyclic Reactions / Chapter 11.： |
| Electrocyclic Reactions / 11.1.： |
| Sigmatropic Rearrangements / 11.2.： |
| Cycloaddition Reactions / 11.3.： |
| Free-Radical Reactions / Chapter 12.： |
| Generation and Characterization of Free Radicals / 12.1.： |
| Background / 12.1.1.： |
| Stable and Persistent Free Radicals / 12.1.2.： |
| Direct Detection of Radical Intermediates / 12.1.3.： |
| Sources of Free Radicals / 12.1.4.： |
| Structural and Stereochemical Properties of Radical Intermediates / 12.1.5.： |
| Charged Radical Species / 12.1.6.： |
| Characteristics of Reaction Mechanisms Involving Radical Intermediates / 12.2.： |
| Kinetic Characteristics of Chain Reactions / 12.2.1.： |
| Free-Radical Substitution Reactions / 12.2.2.： |
| Oxidation / 12.3.1.： |
| Free-Radical Addition Reactions / 12.4.： |
| Addition of Hydrogen Halides / 12.4.1.： |
| Addition of Halomethanes / 12.4.2.： |
| Addition of Other Carbon Radicals / 12.4.3.： |
| Addition of Thiols and Thiocarboxylic Acids / 12.4.4.： |
| Halogen, Sulfur, and Selenium Group Transfer Reactions / 12.5.： |
| Intramolecular Free-Radical Reactions / 12.6.： |
| Rearrangement and Fragmentation Reactions of Free Radicals / 12.7.： |
| Rearrangement Reactions / 12.7.1.： |
| Fragmentation / 12.7.2.： |
| Electron-Transfer Reactions Involving Transition-Metal Ions / 12.8.： |
| S[subscript RN]1 Substitution Processes / 12.9.： |
| Photochemistry / Chapter 13.： |
| General Principles / 13.1.： |
| Orbital Symmetry Considerations Related to Photochemical Reactions / 13.2.： |
| Photochemistry of Carbonyl Compounds / 13.3.： |
| Photochemistry of Alkenes and Dienes / 13.4.： |
| Photochemistry of Aromatic Compounds / 13.5.： |
| References to Problems |
| Index |
| Chemical Bonding and Structure / Chapter 1.： |
| Valence Bond Description of Chemical Bonding / 1.1.： |
| Orbital Hybridization / 1.1.1.： |
図書
