該書主要講述面對一個有機化學變化如何正確寫出它的反應機理。全文是按照不同反應機理和反應條件安排的，而不同於市面上常見的同類書。該書重點放在用統一的原理將不同的反應聯繫起來。每一章都列舉了常見的反應機理路徑和描述指導。經常遇見對問題和會以“常見錯誤提示”被提及，以此來避免讀者陷入對概念理解的誤區。
基本介紹
- 書名：有機反應機理的書寫藝術
- 作者：格羅斯曼
- 原版名稱：The Art of Writing Reasonable Organic Reaction Mechanisms
- ISBN：9787030333018
- 類別：理論專著/研究生教育
- 頁數：355
- 定價：80.00元
- 出版社：科學出版社
- 出版時間：2012-1
- 裝幀：平裝
- 開本：B5
- 叢書：國外化學經典教材系列（影印版）
內容介紹,目錄,專家評論,
內容介紹
《有機反應機理的書寫藝術(原著第2版)》內容簡介：每一個滿懷抱負的有機化學家都嘗試寫出合理的有機反應機理，然而市面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(原著第2版)》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(原著第2版)》的突出特點體現在：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，烯烴複分解反應、芳香環化反應等在《有機反應機理的書寫藝術(原著第2版)》中均有所涉及。
目錄
Preface to the Student
Preface to the Instructor
1 The Basics
1.1 Structure and Stability of Organic Compounds
1.1.1 Conventions of Drawing Structures;Grossman's Rule
1.1.2 Lewis Structures;Resonance Structures
1.1.3 Molecular Shape;Hybridization
1.1.4 Aromaticity
1.2 Brønsted Acidity and Basicity
1.2.1 pKaValues
1.2.2 Tautomerism
1.3 Kinetics and Thermodynamics
1.4 Getting Started in Drawing a Mechanism
1.5 Classes of Overall Transformations
1.6 Classes of Mechanisms
1.6.1 Polar Mechanisms
1.6.2 Free-Radical Mechanisms
1.6.3 Pericyclic Mechanisms
1.6.4 Transition-Metal-Catalyzed and-Mediated Mechanisms
1.7 Summary
Problems
2 Polar Reactions under Basic Conditions
2.1 Substitution and Elimination at C(Sp)-XσBonds,Part 1
2.1.1 Substitution by the SN2 Mechanism
2.1.2 β-Elimination by the E2 and Elcb Mechanisms
2.1.3 Predicting Substitution vs.Elimination
2.2 Addition of Nucleophiles to ElectrophilicπBonds
2.2.1 Addition to Carbonyl Compounds
2.2.2 Conjugate Addition;The Michael Reaction
2.3 Substitution at C(Sp)-XσBonds
2.3.1 Substitution at Carbonyl C
2.3.2 Substitution at Alkenyl and Aryl C
2.3.3 Metal Insertion;Halogen-Metal Exchange
2.4 Substitution and Elimination at C(Sp)-XσBonds,Part Ⅱ
2.4.1 Substitution by the SRN1 Mechanism
2.4.2 Substitution by the Elimination-Addition Mechanism
2.4.3 Substitution by the One-Electron Transfer Mechanism
2.4.4 Metal Insertion;Halogen-Metal Exchange
2.4.5 α-Elimination;Generation and Reactions of Carbenes
2.5 Base-Promoted Rearrangements
2.5.1 Migration from C to C
2.5.2 Migration from C to 0 or N
2.5.3 Migration from B to C or 0
2.6 Two Multistep Reactions
2.6.1 The Swem Oxidation
2.6.2 The Mitsunobu Reaction
2.7 Summary
Problems
3 Polar Reactions Under Acidic Conditions
3.1 Carbocations
3.1.1 Carbocation Stability
3.1.2 Carbocation Generation;The Role of Protonation
3.1.3 Typical Reactions of Carbocations;Rearrangements
3.2 Substitution and β-Elimìnation Reactions at C(Sp)-X
3.2.1 Substitution by the SNl and SN2 Mechanisms
3.2.2 ?-Elimination by the El Mechanism
3.2.3 Predicting Substitution vs.Elimination
3.3 Electrophilic Addition to Nucleophilic C=C π Bonds
3.4 Substitution at NucleophiJic C=C π Bonds
3.4.1 Electrophilic Aromatic Substitution
3.4.2 Aromatic Substitution of Anilines via Diazonium Salts
3.4.3 Electrophilic Aliphatic Substitution
3.5 Nucleophilic Addition to and Substitution at Electrophilic π Bonds
3.5.1 Heteroatom Nucleophiles
3.5.2 Carbon Nucleophiles
3.6 Summary
Problems
4 Pericyclic Reactions
4.1 lntroduction
4.1.1 Classes of Pericyclic Reactions
4.1.2 Polyene MOs
4.2 Electrocyclic Reactions
4.2.1 Typical Reactions
4.2.2 Stereospeficity
4.2.3 Stereoselectivity
4.3 Cycloadditions
4.3.1 Typical Reactions
4.3.2 Regioselectivity
4.3.3 Stereospecificity
4.3.4 Stereoselectivity
4.4 Sigmatropic Rearrangements
4.4.1 Typical Reactions
4.4.2 Stereospecificity
4.4.3 Stereoselectivity
4.5 Ene Reactions
4.6 Summary
Problems
5 Free-Radical Reactions
5.1 Free Radicals
5.1.1 StabiIity
5.1.2 Generation from Closed-Shell Species
5.1.3 Typical Reactions
5.1.4 Chain vs.Nonchain Mechanisms
5.2 Chain Free-Raclical Reactions
5.2.1 Substitution Reactions
5.2.2 Addition and Fragmentation Reactions
5.3 Nonchain Free-Raclical Reactions
5.3.1 Photochemical Reactions
5.3.2 Reductions and Oxidations with Metals
5.3.3 Cycloaromatizations
5.4 MiscelIaneous Radical Reactions
5.4.1 1,2-Anionic Rearrangements;Lone-Pair Inversion
5.4.2 Triplet Carbenes and Nitrenes
5.5 Summary
Problems
6 Transition-Metal-Mediated and-Catalyzed Reactions
6.1 Introduction to the Chernistry of Transition Metals
6.1.1 Conventions of Drawing Structures
6.1.2 Counting Electrons
6.1.3 Typical Reactions
6.1.4 Stoichiometric vs.Catalytic Mechanisms
6.2 Addition Reactions
6.2.1 Late-Metal-Catalyzed Hydrogenation and Hydrometallation(Pd,Pt,Rh)
6.2.2 Hydroformylation(Co,Rh)
6.2.3 Hydrozirconation(Zr)
6.2.4 Alkene Polymerization(Ti,Zr,Sc,and others)
6.2.5 Cyclopropanation,Epoxidation,and Aziridination of Alkenes(Cu,Rh,Mn,Ti)
6.2.6 Dihydroxylation and Arninohydroxylation of Alkenes(Os)
6.2.7 Nucleophilic Addition to Alkenes and Alkynes(Hg,Pd)
6.2.8 Conjugate Addition Reactions(Cu)
6.2.9 Reductive Coupling Reactions(Ti,Zr)
6.2.10 Pauson-Khand Reaction(Co)
6.2.11 D?tz Reaction(Cr)
6.2.12 Metal-Catalyzed Cycloaddition and Cyclotrimerization(Co,Ni,Rh)
6.3 Substitution Reactions
6.3.1 Hydrogenolysis(Pd)
6.3.2 Carbonylation of A1kyl Halides(Pd,Rh)
6.3.3 Heck Reaction(Pd)
6.3.4 Coupling Reactions Between Nucleophiles and C(Sp)X:Kumada,Stille,Suzul?,Negishi,Buchwald-Hartwig,Sonogashira,and Ullmann Reactions(Ni,Pd,Cu)
6.3.5 Allylic Substitution(Pd)
6.3.6 Pd-Catalyzed Nucleophilic Substitution of Alkenes;Wacker Oxidation
6.3.7 Tebbe Reaction(Ti)
6.3.8 Propargyl Substitution in Co-Alkyne Complexes
6.4 Rearrangement Reactions
6.4.1 Alkene Isomerization(Rh)
6.4.2 Olefm and Alkyne Metathesis(Ru,W,Mo,Ti)
6.5 Elimination Reactions
6.5.1 Oxidation of Alcohols(Cr,Ru)
6.5.2 Decarbonylation of Aldehydes(Rh)
6.6 Summary
Problems
7 Mixed-Mechanism Problems
A Final Word
Index
專家評論
“這是一部優秀並完美表達的作品……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表述 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了，學生們一致對本書的透徹敘述和書中試題的覆蓋面給予高度讚譽……正如本書的宗旨：教會學生準確寫出陌生的有機反應的機理。”——Amy Howell,Synthesis
