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Aromaticity | p. 1 |
Structure of Benzene | p. 2 |
Stability of the Benzene Ring | p. 2 |
The Huckel Rule | p. 5 |
Nomenclature | p. 11 |
Aromatic Substitution | p. 15 |
Electrophilic Aromatic Substitution (S[subscript E]Ar) | p. 16 |
Reactivity and Orientation in Electrophilic Aromatic Substitution | p. 20 |
The Hammett Equation | p. 31 |
Nucleophilic Aromatic Substitution | p. 33 |
ipso Substitution | p. 35 |
Alkylbenzenes and Arylbenzenes | p. 38 |
Source of Alkylbenzenes | p. 38 |
Introduction of Alkyl Groups | p. 39 |
Reactions of Alkylbenzenes | p. 42 |
Aryl Derivatives of Benzene | p. 44 |
Phenols | p. 47 |
Industrial Synthetic Methods | p. 47 |
Laboratory Syntheses | p. 48 |
The Acidity of Phenols | p. 50 |
Reactions of the Hydroxy Group | p. 51 |
Reactions of the Ring | p. 53 |
Dihydroxybenzenes | p. 55 |
Aromatic Acids | p. 58 |
Introduction of Acidic Groups | p. 58 |
Reactions of Aromatic Acids | p. 60 |
Acidity of Aromatic Acids | p. 63 |
Compounds with More Than One Acidic Group | p. 64 |
Side-chain Acids | p. 65 |
Aromatic Aldehydes, Ketones and Alcohols | p. 67 |
Aromatic Alcohols | p. 67 |
Aromatic Aldehydes | p. 68 |
Aromatic Ketones | p. 76 |
Nitro Compounds | p. 79 |
Introduction of the Nitro Group | p. 79 |
Charge Transfer Complexes | p. 83 |
Reactions of Nitro Compounds | p. 83 |
Nitrosobenzene and Phenylhydroxylamine | p. 85 |
Aromatic Amines and Diazonium Salts | p. 88 |
Introduction of the Amino Group | p. 89 |
Reactions of Aromatic Amines | p. 91 |
Related Compounds | p. 93 |
Basicity of Amines | p. 94 |
Diazonium Salts | p. 95 |
Aromatic Halogen Compounds | p. 104 |
Synthesis of Aryl Halides | p. 105 |
Reactions of Aryl Halides | p. 108 |
Aromatic Halogen Compounds Substituted in the Side Chain | p. 111 |
Organometallic Reactions | p. 114 |
Grignard and Organolithium Reagents | p. 114 |
Electrophilic Metallation | p. 118 |
Transition Metal Mediated Processes | p. 119 |
Aryl Coupling Reactions | p. 121 |
Arene-Chromium Tricarbonyl Complexes | p. 125 |
Oxidation and Reduction of Aromatic Compounds | p. 129 |
Reduction of the Benzene Ring | p. 129 |
Oxidation of the Benzene Ring | p. 131 |
Polycyclic Aromatic Hydrocarbons | p. 135 |
Chemistry of Naphthalene | p. 135 |
Chemistry of Anthracene | p. 141 |
Chemistry of Phenanthrene | p. 143 |
Further Reading | p. 146 |
Answers to Problems | p. 148 |
Subject Index | p. 166 |
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