Advanced Organic Chemistry-高等有机化学（双语版）

本书第1章介绍了分子结构和化学键与反应活性的定性关系；第2章为立体化学，主要介绍了立体异构、消旋化合物的拆分、立体选择性和立体特异性反应、不对称合成等；第3章主要介绍有机反应的类型，通过举例来解释反应机理，并结合机理讨论反应中间体的结构、稳定性和化学性质；第4章讨论亲核取代反应的机理、立体化学和影响因素；第5章讨论加成和消除反应的机理和立体化学；第6章主要介绍羰基化合物的亲核加成反应；第7章介绍重排反应；第8章讨论芳香亲核和亲电取代反应，同时介绍定位效应；第9章介绍各类氧化和还原反应及歧化反应；第10章介绍周环反应。每章后附有相关习题、专业术语词汇表。为方便学生理解，每章后有中文列出的知识要点。
本书可供化学类专业高年级本科生和研究生使用，亦可供从事高等有机化学教学的教师参考。
　　

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 SN1, 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