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 Structure1
1.1 Localized chemical bonding1
1.2 Dipole moments3
1.3 Inductive effects and field effects3
1.4 Delocalized chemical bonding4
1.5 Resonance structures drawn for conjugated structures6
1.6 Conjugative effect7
1.7 Hyperconjugative effect8
1.8 Steric effect10
1.9 Aromaticity and Hückel’s rule11
Problems19
Vocabulary20
知识要点21
Chapter 2 Stereochemistry26 Chapter 1 Chemical Bonding and Molecular Structure1
1.1 Localized chemical bonding1
1.2 Dipole moments3
1.3 Inductive effects and field effects3
1.4 Delocalized chemical bonding4
1.5 Resonance structures drawn for conjugated structures6
1.6 Conjugative effect7
1.7 Hyperconjugative effect8
1.8 Steric effect10
1.9 Aromaticity and Hückel’s rule11
Problems19
Vocabulary20
知识要点21
Chapter 2 Stereochemistry26
2.1 Enantiomers27
2.2 Resolution of racemates36
2.3 The stereochemistry in reaction process39
Problems47
Vocabulary48
知识要点49
Chapter 3 Mechanisms of Organic Reactions52
3.1 Types of organic reactions52
3.2 The variables of organic reactions56
3.3 How do organic reactions occur: mechanisms59
3.4 Describing a reaction: intermediates62
3.5 Methods of determining mechanisms68
Problems70
Vocabulary70
知识要点71
Chapter 4 Nucleophilic Substitution74
4.1 Mechanisms of nucleophilic substitutions75
4.2 Stereochemistry of nucleophilic substitutions76
4.3 Nucleophiles and nucleophilicity77
4.4 The factors that can influence the rates of SN1, SN2 reactions79
4.5 Neighboring-group participation effect82
Problems85
Vocabulary87
知识要点87
Chapter 5 Addition and Elimination Reactions91
5.1 Electrophilic addition reactions91
5.2 Elimination reactions96
5.3 Elimination vs substitution102
Problems102
Vocabulary104
知识要点105
Chapter 6 Reactions of Carbonyl Compounds107
6.1 The nucleophilic addition reaction mechanisms107
6.2 The nucleophilic addition reactions to the carbonyl groups107
6.3 The addition and elimination reactions111
6.4 The reactivity and stereoselectivity of nucleophilic additions112
6.5 Condensation reactions113
6.6 Reaction with ylides120
6.7 The nucleophilic substitutions of carboxylic acid and their derivatives121
Problems124
Vocabulary125
知识要点126
Chapter 7 Rearrangements129
7.1 Nucleophilic rearrangements129
7.2 Electrophilic rearrangements140
7.3 Rearrangements on aromatic rings143
Problems146
Vocabulary147
知识要点148
Chapter 8 Electrophilic and Nucleophilic Aromatic Substitutions150
8.1 Electrophilic aromatic substitution150
8.2 Specific electrophilic aromatic substitution reactions151
8.3 Directing effects of substituents158
8.4 Effects of multiple substituents on electrophilic aromatic substitution159
8.5 Nucleophilic aromatic substitution160
Problems164
Vocabulary165
知识要点166
Chapter 9 Oxidation and Reduction Reactions167
9.1 Oxidation of alkenes and alkynes167
9.2 Oxidation of alcohols169
9.3 Oxidation of aldehydes and ketones173
9.4 Oxidation of aromatic side chains and the aromatic rings175
9.5 Reduction reactions175
9.6 Other reduction reactions184
9.7 Disproportionation reactions187
Problems188
Vocabulary189
知识要点189
Chapter 10 Pericyclic Reactions193
10.1 Electrocyclic ring opening/closure reactions193
10.2 Cycloaddition reactions197
10.3 Sigmatropic rearrangements204
Problems207
Vocabulary209
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
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