　　每一個滿懷抱負的有機化學傢都嘗試寫齣閤理的有機反應機理，然而市麵上的有關機理正確書寫的書籍卻寥寥無幾。《有機反應機理的書寫藝術》將幫助學生和科研人員提高這一重要技能。《有機反應機理的書寫藝術》的突齣特點體現在：正確的書寫形式，“常見錯誤提示”，配以大量的難度適宜的問題。其另一個特色是包含過渡金屬參與或催化的反應章節。相對新的課題，例如，烯烴復分解反應、芳香環化反應等在本《有機反應機理的書寫藝術》均有所涉及。
　　全新修訂的第2版精彩呈現：更新的反應機理，芳香性的討論，酸性，立體化學的拓展，重新組織瞭自由基反應和金屬參與或催化的反應等內容，增加瞭新的問題。

精彩書評

　　“這是一部優秀並完美錶達的作品……作者……成功地將反應活性和選擇性的核，小觀點視為一個有機整體詳盡錶述簡潔的文風，精選的實例……每一章末對要點簡明的概括，使得讀者很容易鞏固學到的知識……這本書不失為一個小小的藝術品。”
　　——Jens Hartung ，Angewandte Chemie International Edition
　　
　　“我使用該書教授學分課程已經三年時間瞭，學生們一緻對本書的透徹敘述和書中試題的覆蓋麵給予高度贊譽……正如本書的宗旨：教會學生準確寫齣陌生的有機反應的機理”
　　——Amy Howell，Synthesis

Contents
Preface to the Student v
Preface to the Instructor ix
1 The Basics 1
1.1 Structure and Stability of Organic Compounds 1
1.1.1 Conventions of Drawing Structures; Grossman's Rule 1
1.1.2 Lewis Structures; Resonance Structures 3
1.1.3 Molecular Shape; Hybridization 9
1.2 BrOnsted Acidity and Basicity 16
1.3 Kinetics and Thermodynamics 20
1.4 Getting Started in Drawing a Mechanism 22
1.5 Classes of Overall Transformations 25
1.6 Classes ofMechanisms 26
1.6.1 Polar Mechanisms 27
1.6.2 Free-Radical Mechanisms 38
1.6.3 Pericyclic Mechanisms 41
1.6.4 Transition-Metal-Catalyzed and Mediated -Mechanisms 42
2 Polar Reactions under Basic Conditions50
2.1 Substitution and Elimination at C(sp3)-Bonds， Part I 50
2.1.1 Substitution by the SN2 Mechanism 51
2.1.2 β-Elimination by the E2 and Elcb Mechanisms 53
2.1.3 Predicting Substitution vs Elimination 56
2.2 Addition of Nucleophiles to Electrophilic 7r Bonds 58
2.2.1 Addition to Carbonyl Compounds 58
2.2.2 Conjugate Addition; The Michael Reaction 67
2.3 Substitution at C(sp2)-X u Bonds 69
2.3.1 Substitution at Carbonyl C 69
2.3.2 Substitution at Alkenyl and Aryl C 74
2.3.3 Metallnsertion; Halogen-Metal Exchange 78
2.4 Substitution and Elimination at C(sp3)-X cr Bonds， Part II 80
2.4.1 Substitution by the SRNl Mechanism 80
2.4.2 Substitution by the Elimination-Addition Mechanism 81
2.4.3 Substitution by the One-Electron Transfer Mechanism 82
2.4.4 Metallnsertion; Halogen-Metal Exchange 83
2.4.5 α-Elimination; Generation and Reactions of Carbenes 84
2.5 Base-Promoted Rearrangements 87
2.5.1 Migration from C to C 88
2.5.2 Migration from C to O or N 90
2.5.3 Migration from B to C or O 91
2.6 Two Multistep Reactions 92
2.6.1 The Swern Oxidation 92
2.6.2 The Mitsunobu Reaction 94
3 Polar Reactions Under Acidic Conditions105
3.1.1 Carbocation Stability 106
3.1.2 Carbocation Generation; The Role of Protonation 109
3.1.3 Typical Reactions ofCarbocations; Rearrangements 112
3.2 Substitution and p-Elnuination Reactions at C(sp3)-X 117
3.2.1 Substitution by the SNl and SN2 Mechanisms 117
3.2.2 β-Elimination by the El Mechanism 120
3.2.3 Predicting Substitution vs Elimination 122
3.3 Electrophilic Addition to Nucleophilic C=C 7r Bonds 122
3.4 Substitution at Nucleophilic C=C 7r Bonds 125
3.4.1 Electrophilic Aromatic Substitution 125
3.4.2 Aromatic Substitution of Anilines via Diazonium Salts 129
3.4.3 Electrophilic Aliphatic Substitution 131
3.5 Nucleophilic Addition to and Substitution at Electrophilic π Boods 132
3.5.1 Heteroatom Nucleophiles 132
3.5.2 Carbon Nucleophiles 136
4 Pericyclic Reactions 148
4.1.1 Classes ofPericyclic Reactions 148
4.2 Electrocyclic Reactions 156
4.2.1 Typical Reactions 156
4.2.2 Stereospecificity 163
4.2.3 Stereoselectivity 168
4.3 Cycloadditions 170
4.3.1 Typical Reactions 170
4.3.2 Regioselectivity 183
4.3.3 Stereospecificity 184
4.3.4 Stereoselectivity 191
4.4 Sigmatropic Rearrangements 195
4.4.1 TypicalReactions 195
4.4.2 Stereospecificity 201
4.4.3 Stereoselectivity 206
4.5 Ene Reactions 210
5 Free-Radical Reactions 224
5.1.1 Stability 224
5.1.2 Generation from Closed-Shell Species 227
5.1.3 Typical Reactions 232
5.1.4 Chain vs Nonchain Mechanisms 238
5.2 Chain Free-Radical Reactions 239
5.2.1 Substitution Reactions 239
5.2.2 Addition and Fragmentation Reactions 244
5.3 Nonchain Free-Radical Reactions 252
5.3.1 Photochemical Reactions 252
5.3.2 Reductions and Oxidations with Metals 254
5.3.3 Cycloaromatizations 261
5.4 Miscellaneous Radical Reactions 261
5.4.1 1，2-Anionic Rearrangements; Lone-Pairlnversion 261
5.4.2 Triplet Carbenes and Nitrenes 262
6 Transition-Metal-Mediated and -Catalyzed Reactions 270
6.1 Introduction to the Chemistry of Transition Metals 270
6.1.1 Conventions of Drawing Structures 270
6.1.2 Counting Electrons 271
6.1.3 Typical Reactions 276
6.1.4 Stoichiometric vs Catalytic Mechanisms 282
6.2 Addition Reactions 283
6.2.1 Late-Metal-Catalyzed Hydrogenation and Hydrometallation (Pd， Pt， Rh) 283
6.2.2 Hydroformylation (Co， Rh) 286
6.2.3 Hydrozirconation (Zr) 287
6.2.4 Alkene Polymerization (Ti， Zr， Sc， and others) 288
6.2.5 Cyclopropanation， Epoxidation， and Aziridination of Alkenes (Cu， Rh， Mn， Ti) 290
6.2.6 Dihydroxylation and Aminohydroxylation of Alkenes(Os) 292
6.2.7 Nucleophilic Addition to Alkenes and Alkynes (Hg，Pd) 294
6.2.8 Conjugate Addition Reactions (Cu) 297
6.2.9 Reductive Coupling Reactions (Ti， Zr) 297
6.2.10 Pauson-Khand Reaction (Co) 301
6.2.12 Metal-Catalyzed Cycloaddition and Cyclotrimerization (Co， Ni， Rh) 306
6.3 Substitution Reactions 309
6.3.1 Hydrogenolysis (Pd) 309
6.3.2 Carbonylation of Alkyl Halides (Pd， Rh) 311
6.3.4 Coupling Reactions Between Nucleophiles and C(sp2)-X: