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Preface | |
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Molecular Orbital Theory | |
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The Atomic Orbitals of a Hydrogen Atom | |
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Molecules made from Hydrogen Atoms | |
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The H<sub>2</sub> Molecule | |
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The H<sub>3</sub> Molecule | |
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The H<sub>4</sub> �Molecule� | |
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C-H and C-C Bonds | |
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The Atomic Orbitals of a Carbon Atom | |
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Methane | |
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Methylene | |
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Hybridisation | |
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C-C � Bonds and � Bonds: Ethane | |
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C=C � Bonds: Ethylene | |
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Conjugation-H�ckel Theory | |
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The Allyl System | |
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Butadiene | |
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Longer Conjugated Systems | |
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Aromaticity | |
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Aromatic Systems | |
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Antiaromatic Systems | |
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The Cyclopentadienyl Anion and Cation | |
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Homoaromaticity | |
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Spiro Conjugation | |
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Strained � Bonds-Cyclopropanes and Cyclobutanes | |
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Cyclopropanes | |
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Cyclobutanes | |
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Heteronuclear Bonds, C-M, C-X and C=O | |
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Atomic orbital energies and electronegativity | |
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C-X � Bonds | |
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C-M � Bonds | |
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C=O � Bonds | |
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Heterocyclic Aromatic Systems | |
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The Tau Bond Model | |
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Spectroscopic Methods | |
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Ultraviolet Spectroscopy | |
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Photoelectron Spectroscopy | |
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Nuclear Magnetic Resonance Spectroscopy | |
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Electron Spin Resonance Spectroscopy | |
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Exercises | |
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The Structures of Organic Molecules | |
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The Effects of � Conjugation | |
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A Notation for Substituents | |
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The Effect of Substituents on the Stability of Alkenes | |
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The Effect of Substituents on the Stability of Carbocations | |
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The Effect of Substituents on the Stability of Carbanions | |
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The Effect of Substituents on the Stability of Radicals | |
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Energy-Raising Conjugation | |
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� Conjugation-Hyperconjugation | |
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C-H and C-C Hyperconjugation | |
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C-M Hyperconjugation | |
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Negative Hyperconjugation | |
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The Configurations and Conformations of Molecules | |
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Restricted Rotation in �-Conjugated Systems | |
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Preferred Conformations from Conjugation in the � Framework | |
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Other Noncovalent Interactions | |
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The Hydrogen Bond | |
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Hypervalency | |
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Polar Interactions, and van der Waals and other Weak Interactions | |
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Exercises | |
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Chemical Reactions-How Far and How Fast | |
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Factors Affecting the Position of an Equilibrium | |
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The Principle of Hard and Soft Acids and Bases (HSAB) | |
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Transition Structures | |
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The Perturbation Theory of Reactivity | |
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The Salem-Klopman Equation | |
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Hard and Soft Nucleophiles and Electrophiles | |
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Other Factors Affecting Chemical Reactivity | |
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Ionic Reactions-Reactivity | |
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Single Electron Transfer (SET) in Ionic Reactions | |
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Nucleophilicity | |
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Heteroatom Nucleophiles | |
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Solvent Effects | |
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Alkene Nucleophiles | |
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The �-Effect | |
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Ambident Nucleophiles | |
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Thiocyanate Ion, Cyanide Ion and Nitrite Ion (and the Nitronium Cation) | |
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Enolate Ions | |
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Allyl Anions | |
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Aromatic Electrophilic Substitution | |
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Electrophilicity | |
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Trigonal Electrophiles | |
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Tetrahedral Electrophiles | |
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Hard and Soft Electrophiles | |
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Ambident Electrophiles | |
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Aromatic Electrophiles | |
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Aliphatic Electrophiles | |
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Carbenes | |
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Nucleophilic Carbenes | |
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Electrophilic Carbenes | |
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Aromatic Carbenes | |
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Exercises | |
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Ionic Reactions-Stereochemistry | |
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The Stereochemistry of the Fundamental Organic Reactions | |
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Substitution at a Saturated Carbon | |
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Elimination Reactions | |
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Nucleophilic and Electrophilic Attack on a � Bond | |
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The Stereochemistry of Substitution at Trigonal Carbon | |
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Diastereoselectivity | |
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Nucleophilic Attack on a Double Bond with Diastereotopic Faces | |
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Nucleophilic and Electrophilic Attack on Cycloalkenes | |
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Electrophilic Attack on Open-Chain Double Bonds with Diastereotopic Faces | |
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Diastereoselective Nucleophilic and Electrophilic Attack on Double Bonds Free of Steric Effects | |
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Exercises | |
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Thermal Pericyclic Reactions | |
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The Four Classes of Pericyclic Reactions | |
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Evidence for the Concertedness of Bond Making and Breaking | |
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Symmetry-Allowed and Symmetry-Forbidden Reactions | |
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The Woodward-Hoffmann Rules-Class by Class | |
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The Generalised Woodward-Hoffmann Rule | |
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Explanations for the Woodward-Hoffmann Rules | |
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The Aromatic Transition Structure | |
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Frontier Orbitals | |
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Correlation Diagrams | |
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Secondary Effects | |
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The Energies and Coefficients of the Frontier Orbitals of Alkenes and Dienes | |
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Diels-Alder Reactions | |
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1,3-Dipolar Cycloadditions | |
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Other Cycloadditions | |
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Other Pericyclic Reactions | |
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Periselectivity | |
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Torquoselectivity | |
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Exercises | |
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Radical Reactions | |
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Nucleophilic and Electrophilic Radicals | |
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The Abstraction of Hydrogen and Halogen Atoms | |
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The Effect of the Structure of the Radical | |
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The Effect of the Structure of the Hydrogen or Halogen Source | |
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The Addition of Radicals to � Bonds | |
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Attack on Substituted Alkenes | |
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Attack on Substituted Aromatic Rings | |
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Synthetic Applications of the Chemoselectivity of Radicals | |
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Stereochemistry in some Radical Reactions | |
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Ambident Radicals | |
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Neutral Ambident Radicals | |
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Charged Ambident Radicals | |
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Radical Coupling | |
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Exercises | |
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Photochemical Reactions | |
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Photochemical Reactions in General | |
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Photochemical Ionic Reactions | |
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Aromatic Nucleophilic Substitution | |
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Aromatic Electrophilic Substitution | |
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Aromatic Side-Chain Reactivity | |
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Photochemical Pericyclic Reactions and Related Stepwise Reactions | |
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The Photochemical Woodward-Hoffmann Rule | |
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Regioselectivity of Photocycloadditions | |
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Other Kinds of Selectivity in Pericyclic and Related Photochemical Reactions | |
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Photochemically Induced Radical Reactions | |
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Chemiluminescence | |
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Exercises | |
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References | |
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Index | |