本書第1章介紹了分子結構和化學鍵與反應活性的定性關系；第2章為立體化學，主要介紹了立體異構、消旋化合物的拆分、立體選擇性和立體特異性反應、不對稱合成等；第3章主要介紹有機反應的類型，通過舉例來解釋反應機理，并結合機理討論反應中間體的結構、穩定性和化學性質；第4章討論親核取代反應的機理、立體化學和影響因素；第5章討論加成和消除反應的機理和立體化學；第6章主要介紹羰基化合物的親核加成反應；第7章介紹重排反應；第8章討論芳香親核和親電取代反應，同時介紹定位效應；第9章介紹各類氧化和還原反應及歧化反應；第10章介紹周環反應。每章后附有相關習題、專業術語詞匯表。為方便學生理解，每章后有中文列出的知識要點。
本書可供化學類專業高年級本科生和研究生使用，亦可供從事高等有機化學教學的教師參考。
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
知識要點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
知識要點21
Chapter 2 Stereochemistry26
2.1 Enantiomers27
2.2 Resolution of racemates36
2.3 The stereochemistry in reaction process39
Problems47
Vocabulary48
知識要點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
知識要點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
知識要點87
Chapter 5 Addition and Elimination Reactions91
5.1 Electrophilic addition reactions91
5.2 Elimination reactions96
5.3 Elimination vs substitution102
Problems102
Vocabulary104
知識要點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
知識要點126
Chapter 7 Rearrangements129
7.1 Nucleophilic rearrangements129
7.2 Electrophilic rearrangements140
7.3 Rearrangements on aromatic rings143
Problems146
Vocabulary147
知識要點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
知識要點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
知識要點189
Chapter 10 Pericyclic Reactions193
10.1 Electrocyclic ring opening/closure reactions193
10.2 Cycloaddition reactions197
10.3 Sigmatropic rearrangements204
Problems207
Vocabulary209
知識要點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
參考文獻227
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