出版时间:2012-1 出版社:科学出版社 作者:格罗斯曼 页数:355
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内容概要
每一个满怀抱负的有机化学家都尝试写出合理的有机反应机理,然而市面上的有关机理正确书写的书籍却寥寥无几。《有机反应机理的书写艺术(原著第2版)》将帮助学生和科研人员提高这一重要技能。《有机反应机理的书写艺术(原著第2版)》的突出特点体现在:正确的书写形式,“常见错误提示”,配以大量的难度适宜的问题。其另一个特色是包含过渡金属参与或催化的反应章节。相对新的课题,例如,烯烃复分解反应、芳香环化反应等在《有机反应机理的书写艺术(原著第2版)》中均有所涉及。
全新修订的第2版精彩呈现:更新的反应机理,芳香性的讨论,酸性,立体化学的拓展,重新组织了自由基反应和金属参与或催化的反应等内容,增加了新的问题。
作者简介
作者:(美国)格罗斯曼(Robert B.Grossman)
书籍目录
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 BrCnsted Acidity and Basicity
1.2.1 PK Values
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(sp3)一X Bonds.Part I
2.1.1 Substitution by the SN2 Mechanism
2.1.2 Elimination by the E2 and Elcb Mechanisms
2.1.3 Predicting Substitution VS.Elimination
2.2 Addition of Nucleophiles to Electrophilic仃Bonds
2.2.1 Addition to Carbonyl Compounds
2.2.2 Conjugate Addition;The Michael Reaction
2.3 Substitution at C(sp2)一X Bouds
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(sp3)-X Bonds,Part II
2.4.1 Substitution by the SRNl 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一Metal Exchange
2.4.5 Ol-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 O or N
2.5.3 Migration from B to C or O
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 一Elimination Reactions at C(sp3)一X
3.2.1 Substitution by the SNl and SN2 Mechanisms
3.2.2 Elimination by the E1 Mechanism
3.2.3 Predicting Substitution VS.Elimination
3.3 Electrophilic Addition to Nucleophilic C=C Bonds
3.4 Substitution atNucleophilic C=C 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
Bonds
3.5.1 Heteroatom Nucleophiles
3.5.2 Carbon Nucleophiles
3.6 Summary
Problems
4 Pericyclic Reactions
4.1 Introduction
4.1.1 Classes of Pericyclic Reactions
4.1.2 Polyene MOs
……
5 Free.Radical Reactions
6 Transition-Metal-Mediated and-Cata!vzed Reactions
7 Mixed.Mechanism Probiems
A F.nal Word
Index
章节摘录
版权页:插图:The C and N atoms in CH3'and NH4+both have formalpositive charges.but the C atom is electron-deficient,and the N atom is not.The C and B atoms in CH3 and BF3 are both electron.deficient,but neither is for-mally charged.B is electropositive and N is electronegative,but BH4一and NH4’are both stable ions.as the central atoms are electron-SHfficient.The C atoms inCH3+,CH3I,and HEC=O are all electrophilic,but only the C in CH3’is electron-deficient.The O atom in Me ,has a formal positive charge.but the C atoms are electrophilic,not For each bonding pattem.there are often several ways in which ql"and non-bonding electrons Can be distributed.These different Ways are called resonance structures.Resonance structures are alternative descriptions of a single com-pound.Each resonance structure has some contribution to the real structure of the compound,but no one resonance structure is the true picture.letters,lines,and dots are words in a language that has been developed to describe molecules,and,as in any language。sometimes one word is inadequate,and several differ-ent words must be used to give a complete picture of the structure of a mole-cule.The fact that resonance structures have to be used at all is an artifact of thelanguage used to describe chemical compounds. The true electronic picture of a compound is a weighted average of the dif-ferent resonance structures that can be drawn(resonance hybrid).
媒体关注与评论
“这是一部优秀并完美表达的作品……作者……成功地将反应活性和选择性的核,小观点视为一个有机整体详尽表述 简洁的文风,精选的实例……每一章末对要点简明的概括,使得读者很容易巩固学到的知识……这本书不失为一个小小的艺术品。” ——Jens Hartung ,Angewandte Chemie International Edition “我使用该书教授学分课程已经三年时间了,学生们一致对本书的透彻叙述和书中试题的覆盖面给予高度赞誉……正如本书的宗旨:教会学生准确写出陌生的有机反应的机理” ——Amy Howell,Synthesis
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《有机反应机理的书写艺术(原著第2版)》是国外化学经典教材系列(影印版)。
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