Chapter 1 Chemical Bonding and Molecular Structure 1
1.1 Localized chemical bonding 1
1.2 Dipole moments 3
1.3 Inductive effects and field effects 3
1.4 Delocalized chemical bonding 4
1.5 Resonance structures drawn for conjugated structures 6
1.6 Conjugative effect 7
1.7 Hyperconjugative effect 8
1.8 Steric effect 10
1.9 Aromaticity and Hückel's rule 11
Problems 19
Vocabulary 20
知识要点 21
Chapter 2 Stereochemistry 26
2.1 Enantiomers 27
2.2 Resolution of racemates 36
2.3 The stereochemistry in reaction process 39
Problems 47
Vocabulary 48
知识要点 49
Chapter 3 Mechanisms of Organic Reactions 52
3.1 Types of organic reactions 52
3.2 The variables of organic reactions 56
3.3 How do organic reactions occur:mechanisms 59
3.4 Describing a reaction:intermediates 62
3.5 Methods of determining mechanisms 68
Problems 70
Vocabulary 70
知识要点 71
Chapter 4 Nucleophilic Substitution 74
4.1 Mechanisms of nucleophilic substitutions 75
4.2 Stereochemistry of nucleophilic substitutions 76
4.3 Nucleophiles and nucleophilicity 77
4.4 The factors that can influence the rates of SNl,SN2 reactions 79
4.5 Neighboring-group participation effect 82
Problems 85
Vocabulary 87
知识要点 87
Chapter 5 Addition and Elimination Reactions 91
5.1 Electrophilic addition reactions 91
5.2 Elimination reactions 96
5.3 Elimination vs substitution 102
Problems 102
Vocabulary 104
知识要点 105
Chapter 6 Reactions of Carbonyl Compounds 107
6.1 The nucleophilic addition reaction mechanisms 107
6.2 The nucleophilic addition reactions to the carbonyl groups 107
6.3 The addition and elimination reactions 111
6.4 The reactivity and stereoselectivity of nucleophilic additions 112
6.5 Condensation reactions 113
6.6 Reaction with ylides 120
6.7 The nucleophilic substitutions of carboxylic acid and their derivatives 121
Problems 124
Vocabulary 125
知识要点 126
Chapter 7 Rearrangements 129
7.1 Nucleophilic rearrangements 129
7.2 Electrophilic rearrangements 140
7.3 Rearrangements on aromatic rings 143
Problems 146
Vocabulary 147
知识要点 148
Chapter 8 Electrophilic and Nucleophilic Aromatic Substitutions 150
8.1 Electrophilic aromatic substitution 150
8.2 Specific electrophilic aromatic substitution reactions 151
8.3 Directing effects of substituents 158
8.4 Effects of multiple substituents on electrophilic aromatic substitution 159
8.5 Nucleophilic aromatic substitution 160
Problems 164
Vocabulary 165
知识要点 166
Chapter 9 Oxidation and Reduction Reactions 167
9.1 Oxidation of alkenes and alkynes 167
9.2 Oxidation of alcohols 169
9.3 Oxidation of aldehydes and ketones 173
9.4 Oxidation of aromatic side chains and the aromatic rings 175
9.5 Reduction reactions 175
9.6 Other reduction reactions 184
9.7 Disproportionation reactions 187
Problems 188
Vocabulary 189
知识要点 189
Chapter 10 Pericyclic Reactions 193
10.1 Electrocyclic ring opening/closure reactions 193
10.2 Cycloaddition reactions 197
10.3 Sigmatropic rearrangements 204
Problems 207
Vocabulary 209
知识要点 209
Appendix Ⅰ 《Advanced Organic Chemistry》Final Test（1） 211
Appendix Ⅱ 《Advanced Organic Chemistry》Final Test（2） 216
Appendix Ⅲ 《Advanced Organic Chemistry》Final Test（3） 222
参考文献 227