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| Chemical Bonding and Structure | |
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| Valence Bond Description of Chemical Bonding | |
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| Orbital Hybridization | |
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| Resonance | |
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| Bond Energy, Polarity, and Polarizability | |
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| Bond Energies | |
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| Electronegativity and Polarity | |
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| Polarizability--Hardness and Softness | |
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| Molecular Orbital Theory and Methods | |
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| Huckel Molecular Orbital Theory | |
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| Qualitative Application of Molecular Orbital Theory | |
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| Application of Molecular Orbital Theory to Reactivity | |
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| Interactions between [sigma] and [pi] Systems--Hyperconjugation | |
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| Other Quantitative Descriptions of Molecular Structure | |
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| Atoms in Molecules | |
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| Electron Density Functionals | |
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| Modern Valence Bond Approaches | |
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| General References | |
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| Problems | |
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| Principles of Stereochemistry | |
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| Enantiomeric Relationships | |
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| Diastereomeric Relationships | |
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| Stereochemistry of Reactions | |
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| Prochiral Relationships | |
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| General References | |
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| Problems | |
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| Conformational, Steric, and Stereoelectronic Effects | |
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| Strain and Molecular Mechanics | |
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| Conformations of Acyclic Molecules | |
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| Conformations of Cyclohexane Derivatives | |
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| Carbocyclic Rings Other Than Six-Membered | |
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| The Effect of Heteroatoms on Conformational Equilibria | |
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| The Anomeric Effect | |
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| Conformational Effects on Reactivity | |
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| Angle Strain and Its Effect on Reactivity | |
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| Relationships between Ring Size and Rate of Cyclization | |
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| Torsional and Stereoelectronic Effects on Reactivity | |
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| General References | |
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| Problems | |
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| Study and Description of Organic Reaction Mechanismns | |
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| Thermodynamic Data | |
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| Kinetic Data | |
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| Substituent Effects and Linear Free-Energy Relationships | |
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| Basic Mechanistic Concepts: Kinetic versus Thermodynamic Control, Hammond's Postulate, the Curtin-Hammett Principle | |
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| Kinetic versus Thermodynamic Control | |
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| Hammond's Postulate | |
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| The Curtin-Hammett Principle | |
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| Isotope Effects | |
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| Isotopes in Labeling Experiments | |
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| Characterization of Reaction Intermediates | |
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| Catalysis by Bronsted Acids and Bases | |
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| Lewis Acid Catalysis | |
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| Solvent Effects | |
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| Substituent Effects in the Gas Phase | |
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| Stereochemistry | |
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| Conclusion | |
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| General References | |
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| Problems | |
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| Nucleophilic Substitution | |
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| The Limiting Cases--Substitution by the Ionization (S[subscript N]1) Mechanism | |
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| The Limiting Cases--Substitution by the Direct Displacement (S[subscript N]2) Mechanism | |
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| Detailed Mechanistic Description and Borderline Mechanisms | |
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| Carbocations | |
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| Nucleophilicity and Solvent Effects | |
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| Leaving-Group Effects | |
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| Steric and Strain Effects on Substitution and Ionization Rates | |
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| Effects of Conjugation on Reactivity | |
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| Stereochemistry of Nucleophilic Substitution | |
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| Neighboring-Group Participation | |
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| Mechanism of Rearrangements of Carbocations | |
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| The Norbornyl Cation and Other Nonclassical Carbocations | |
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| General References | |
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| Problems | |
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| Polar Addition and Elimination Reactions | |
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| Addition of Hydrogen Halides to Alkenes | |
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| Acid-Catalyzed Hydration and Related Addition Reactions | |
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| Addition of Halogens | |
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| Electrophilic Additions Involving Metal Ions | |
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| Additions to Alkynes and Allenes | |
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| The E2, E1, and E1cb Mechanisms | |
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| Regiochemistry of Elimination Reactions | |
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| Stereochemistry of E2 Elimination Reactions | |
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| Dehydration of Alcohols | |
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| Eliminations Not Involving C--H Bonds | |
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| General References | |
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| Problems | |
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| Carbanions and Other Nucleophilic Carbon Species | |
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| Acidity of Hydrocarbons | |
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| Carbanions Stabilized by Functional Groups | |
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| Enols and Enamines | |
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| Carbanions as Nucleophiles in S[subscript N]2 Reactions | |
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| General References | |
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| Problems | |
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| Reactions of Carbonyl Compounds | |
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| Hydration and Addition of Alcohols to Aldehydes and Ketones | |
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| Addition-Elimination Reactions of Ketones and Aldehydes | |
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| Addition of Carbon Nucleophiles to Carbonyl Groups | |
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| Reactivity of Carbonyl Compounds toward Addition | |
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| Ester Hydrolysis | |
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| Aminolysis of Esters | |
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| Amide Hydrolysis | |
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| Acylation of Nucleophilic Oxygen and nitrogen Groups | |
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| Intramolecular Catalysis | |
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| General References | |
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| Problems | |
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| Aromaticity | |
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| The Concept of Aromaticity | |
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| The Annulenes | |
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| Aromaticity in Charged Rings | |
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| Homoaromaticity | |
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| Fused-Ring Systems | |
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| Heterocyclic Rings | |
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| General References | |
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| Problems | |
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| Aromatic Substitution | |
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| Electrophilic Aromatic Substitution Reactions | |
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| Structure-Reactivity Relationships | |
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| Reactivity of Polycyclic and Heteroaromatic Compounds | |
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| Specific Substitution Mechanisms | |
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| Nitration | |
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| Halogenation | |
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| Protonation and Hydrogen Exchange | |
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| Friedel-Crafts Alkylation and Related Reactions | |
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| Friedel-Crafts Acylation and Related Reactions | |
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| Coupling with Diazonium Compounds | |
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| Substitution of Groups Other Than Hydrogen | |
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| Nucleophilic Aromatic Substitution by the Addition-Elimination Mechanism | |
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| Nucleophilic Aromatic Substitution by the Elimination-Addition Mechanism | |
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| General References | |
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| Problems | |
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| Concerted Pericyclic Reactions | |
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| Electrocyclic Reactions | |
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| Sigmatropic Rearrangements | |
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| Cycloaddition Reactions | |
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| General References | |
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| Problems | |
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| Free-Radical Reactions | |
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| Generation and Characterization of Free Radicals | |
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| Background | |
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| Stable and Persistent Free Radicals | |
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| Direct Detection of Radical Intermediates | |
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| Sources of Free Radicals | |
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| Structural and Stereochemical Properties of Radical Intermediates | |
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| Charged Radical Species | |
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| Characteristics of Reaction Mechanisms Involving Radical Intermediates | |
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| Kinetic Characteristics of Chain Reactions | |
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| Structure-Reactivity Relationships | |
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| Free-Radical Substitution Reactions | |
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| Halogenation | |
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| Oxidation | |
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| Free-Radical Addition Reactions | |
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| Addition of Hydrogen Halides | |
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| Addition of Halomethanes | |
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| Addition of Other Carbon Radicals | |
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| Addition of Thiols and Thiocarboxylic Acids | |
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| Halogen, Sulfur, and Selenium Group Transfer Reactions | |
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| Intramolecular Free-Radical Reactions | |
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| Rearrangement and Fragmentation Reactions of Free Radicals | |
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| Rearrangement Reactions | |
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| Fragmentation | |
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| Electron-Transfer Reactions Involving Transition-Metal Ions | |
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| S[subscript RN]1 Substitution Processes | |
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| General References | |
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| Problems | |
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| Photochemistry | |
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| General Principles | |
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| Orbital Symmetry Considerations Related to Photochemical Reactions | |
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| Photochemistry of Carbonyl Compounds | |
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| Photochemistry of Alkenes and Dienes | |
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| Photochemistry of Aromatic Compounds | |
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| General References | |
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| Problems | |
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| References to Problems | |
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| Index | |