1Bonding and Isomerism（键合和异构）001 2Alkanes and Cycloalkanes; Conformational and Geometric Isomerism （烷烃和环烷烃；构象和几何异构）031 3Alkenes and Alkynes（烯烃和炔烃）054 4Aromatic Compounds（芳香化合物）094 5Stereoisomerism（立体异构）119 6Organic Halogen Compounds; Substitution and Elimination Reactions （含卤有机化合物；取代反应和消除反应）143 7Alcohols, Phenols, and Thiols（醇，酚和硫醇）162 8Ethers and Epoxides（醚和环氧化合物）184 9Aldehydes and Ketones（醛和酮）200 10Carboxylic Acids and Their Derivatives（羧酸及其衍生物）230 11Amines and Related Nitrogen Compounds（胺和相关含氮化合物）263 12Spectroscopy and Structure Determination（波谱学和结构测定）287 13Heterocyclic Compounds（杂环化合物）315 14Synthetic Polymers（合成高聚物）331 15Lipids and Detergents（脂类和洗涤剂）350 16Carbohydrates（糖类）368 17Amino Acids, Peptides, and Proteins（氨基酸，肽和蛋白质）394 18Nucleotides and Nucleic Acids（核苷酸和核酸）419 Contents 1Bonding and Isomerism（键合和异构）001 1.1How Electrons Are Arranged in Atoms（原子中的电子排布）002 1.2Ionic and Covalent Bonding（离子键和共价键）003 1.3Carbon and the Covalent Bond（碳原子和共价键）006 1.4Carbon?CCarbon Single Bonds（碳-碳单键）007 1.5Polar Covalent Bonds（极性共价键）008 1.6Multiple Covalent Bonds（多重共价键）010 1.7Valence（化合价）011 1.8Isomerism（异构现象）011 1.9Writing Structural Formulas（结构式的书写）012 1.10Abbreviated Structural Formulas（简化结构式）014 1.11Formal Charge（形式电荷）016 1.12Resonance（共振理论）017 1.13Arrow Formalism（箭头形式）018 1.14The Orbital View of Bonding; the Sigma Bond （共价键的轨道理论；σ键）019 1.15Carbon sp3 Hybrid Orbitals（碳的sp3杂化轨道）020 1.16Tetrahedral Carbon; the Bonding in Methane（碳原子的四面体结构；甲烷分子中的碳氢键）022 1.17Classification According to Molecular Framework （按分子骨架分类）023 1.18Classification According to Functional Group（按功能基分类）026 2Alkanes and Cycloalkanes; Conformational and Geometric Isomerism（烷烃和环烷烃；构象和几何异构）031 2.1The Structures of Alkanes（烷烃的结构）032 2.2Nomenclature of Organic Compounds（有机化合物的命名）033 2.3IUPAC Rules for Naming Alkanes（烷烃的IUPAC命名规则）034 2.4Alkyl and Halogen Substituents（烷基和卤素取代基）036 2.5Use of the IUPAC Rules（IUPAC命名规则的应用）037 2.6Sources of Alkanes（烷烃的来源）038 2.7Physical Properties of Alkanes and Nonbonding Intermolecular Interactions（烷烃的物理性质和分子间的非键作用）038 2.8Conformations of Alkanes（烷烃的构象）040 2.9Cycloalkane Nomenclature and Conformation （环烷烃的命名和构象）041 2.10Cis-Trans Isomerism in Cycloalkanes（环烷烃的顺反异构）045 2.11Summary of Isomerism（异构现象小结）046 2.12Reactions of Alkanes（烷烃的化学反应）046 2.13The Free-Radical Chain Mechanism of Halogenation （烷烃卤代的自由基链反应机制）049 3Alkenes and Alkynes（烯烃和炔烃）054 3.1Definition and Classification（定义和分类）055 3.2Nomenclature（命名）056 3.3Some Facts about Double Bonds（碳碳双键的特征）058 3.4The Orbital Model of a Double Bond; the Pi Bond（碳碳双键的轨道模型；π键）059 3.5Cis?CTrans Isomerism in Alkenes（烯烃的顺反异构现象）061 3.6Addition and Substitution Reactions Compared（加成和取代反应的比较）065 3.7Polar Addition Reactions（极性加成反应）065 3.8Addition of Unsymmetric Reagents to Unsymmetric Alkenes; Markovnikov’s Rule（不对称试剂与不对称烯烃的加成；马尔可夫尼可夫规则）067 3.9Mechanism of Electrophilic Addition to Alkenes（烯烃的亲电加成机制）069 3.10Markovnikov’s Rule Explained（马尔可夫尼可夫规则的解释）070 3.11Reaction Equilibrium： What Makes a Reaction Go? （反应平衡：什么使反应能够进行下去？）072 3.12Reaction Rates： How Fast Does a Reaction Go?（反应速率：反应进行得有多快？）073 3.13Hydroboration of Alkenes（烯烃的硼氢化反应）075 3.14Addition of Hydrogen（加氢反应）077 3.15Additions to Conjugated Systems（共轭烯烃的加成反应）078 3.16Free-Radical Additions; Polyethylene （自由基加成反应；聚乙烯）081 3.17Oxidation of Alkenes（烯烃的氧化）082 3.18Some Facts about Triple Bonds（叁键的特征）084 3.19The Orbital Model of a Triple Bond（叁键的轨道模型）084 3.20Addition Reactions of Alkynes（炔烃的加成反应）084 3.21Acidity of Alkynes（炔烃的酸性）086 4Aromatic Compounds（芳香化合物）094 4.1Some Facts about Benzene（有关苯的实验事实）095 4.2The Kekulé Structure of Benzene（苯的凯库勒结构式）096 4.3Resonance Model for Benzene（苯的共振结构模型）096 4.4Orbital Model for Benzene（苯的轨道模型）097 4.5Symbols for Benzene（苯的结构表达式）098 4.6Nomenclature of Aromatic Compounds（芳香族化合物的命名）098 4.7The Resonance Energy of Benzene（苯的共振能）101 4.8Electrophilic Aromatic Substitution（芳香亲电取代反应）102 4.9The Mechanism of Electrophilic Aromatic Substitution（芳香亲电取代反应的机制）103 4.10Ring-Activating and Ring-Deactivating Substituents （苯环的活化基和钝化基）107 4.11Ortho,Para-Directing and Meta-Directing Groups （邻，对位定位基和间位定位基）107 4.12The Importance of Directing Effects in Synthesis （定位效应在合成中的重要性）111 4.13Polycyclic Aromatic Hydrocarbons（多环芳香烃）112 5Stereoisomerism（立体异构）119 5.1Chirality and Enantiomers（手性和对映异构体）120 5.2Stereogenic Centers; the Stereogenic Carbon Atom （手性中心；手性碳原子）121 5.3Configuration and the R-S Convention（R-S 构型）124 5.4Polarized Light and Optical Activity（偏振光和光学活性）127 5.5Properties of Enantiomers（对映异构体的性质）129 5.6Fischer Projection Formulas（费歇尔投影式）130 5.7Compounds with More Than One Stereogenic Center; Diastereomers（具有多个手性中心的化合物；非对映异构体）132 5.8Meso Compounds; the Stereoisomers of Tartaric Acid（内消旋化合物；酒石酸的立体异构体）134 5.9Stereochemistry： A Recap of Definitions（立体化学：定义概述）135 5.10Stereochemistry and Chemical Reactions （立体化学和化学反应）136 5.11Resolution of a Racemic Mixture（外消旋体的拆分）138 6Organic Halogen Compounds; Substitution and Elimination Reactions（含卤有机化合物；取代反应和消除反应）143 6.1Nucleophilic Substitution（亲核取代反应）144 6.2Examples of Nucleophilic Substitutions（亲核取代反应实例）144 6.3Nucleophilic Substitution Mechanisms（亲核取代反应机制）147 6.4The SN2 Mechanism（双分子亲核取代机制）147 6.5The SN1 Mechanism（单分子亲核取代机制）149 6.6The SN1 and SN2 Mechanisms Compared（SN1和SN2反应 机制的比较）151 6.7Dehydrohalogenation, an Elimination Reaction; the E2 and E1 Mechanisms（脱卤化氢，消除反应；双分子消除和单分子消除机制）153 6.8Substitution and Elimination in Competition（取代反应和消除 反应的相互竞争）154 6.9Polyhalogenated Aliphatic Compounds（多卤代脂肪烃）156 7Alcohols, Phenols, and Thiols（醇，酚和硫醇）162 7.1Nomenclature of Alcohols（醇的命名）163 7.2Classification of Alcohols（醇的分类）164 7.3Nomenclature of Phenols（酚的命名）164 7.4Hydrogen Bonding in Alcohols and Phenols （醇和酚分子中的氢键）165 7.5Acidity and Basicity Reviewed（酸性和碱性）166 7.6The Acidity of Alcohols and Phenols（醇和酚的酸性）168 7.7The Basicity of Alcohols and Phenols（醇和酚的碱性）170 7.8Dehydration of Alcohols to Alkenes （醇脱水生成烯烃的反应）170 7.9The Reaction of Alcohols with Hydrogen Halides （醇与卤化氢的反应）172 7.10Other Ways to Prepare Alkyl Halides from Alcohols （由醇制备卤代烃的方法）173 7.11A Comparison of Alcohols and Phenols（醇和酚的比较）174 7.12Oxidation of Alcohols to Aldehydes, Ketones, and Carboxylic Acids（醇的氧化反应——生成醛，酮和羧酸）174 7.13Alcohols with More Than One Hydroxyl Group（多元醇）175 7.14Aromatic Substitution in Phenols（酚的芳香取代反应）176 7.15Oxidation of Phenols（酚的氧化反应）177 7.16Phenols as Antioxidants（酚类抗氧化剂）177 7.17Tests for Phenols（酚的鉴别）178 7.18Thiols, the Sulfur Analogs of Alcohols and Phenols （硫醇，醇和酚的硫类似物）178 8Ethers and Epoxides（醚和环氧化合物）184 8.1Nomenclature of Ethers（醚的命名）185 8.2Physical Properties of Ethers（醚的物理性质）186 8.3Ethers as Solvents（醚作溶剂）186 8.4The Grignard Reagent; an Organometallic Compound（格利雅试剂；一种有机金属化合物）187 8.5Preparation of Ethers（醚的制备）189 8.6Cleavage of Ethers（醚的裂解）190 8.7Epoxides Oxiranes［环氧化物（环氧乙烷）］192 8.8Reactions of Epoxides（环氧化物的反应）192 8.9Cyclic Ethers（环醚）194 9Aldehydes and Ketones（醛和酮）200 9.1Nomenclature of Aldehydes and Ketones（醛和酮的命名）201 9.2Some Common Aldehydes and Ketones（常见的醛和酮）202 9.3Synthesis of Aldehydes and Ketones（醛和酮的制备）203 9.4Aldehydes and Ketones in Nature（天然醛酮）204 9.5The Carbonyl Group（羰基）205 9.6Nucleophilic Addition to Carbonyl Groups： An Overview （羰基的亲核加成：概述）206 9.7Addition of Alcohols： Formation of Hemiacetals and Acetals （与醇加成：生成半缩醛和缩醛）207 9.8Addition of Water; Hydration of Aldehydes and Ketones （与水加成：醛酮的水合）210 9.9Addition of Grignard Reagents and Acetylides （与Grignard试剂和炔化物加成）211 9.10Addition of Hydrogen Cyanide; Cyanohydrins （与氢氰酸加成：生成氰醇）213 9.11Addition of Nitrogen Nucleophiles（与含氮亲核试剂加成）214 9.12Reduction of Carbonyl Compounds（羰基化合物的还原）215 9.13Oxidation of Carbonyl Compounds（羰基化合物的氧化）216 9.14Keto?CEnol Tautomerism（酮式-烯醇式互变异构）217 9.15Acidity of a-Hydrogens; the Enolate Anion （a-氢的酸性；烯醇负离子）218 9.16Deuterium Exchange in Carbonyl Compounds （羰基化合物的氘代）219 9.17Halogenation（卤代反应）220 9.18The Aldol Condensation（醇醛缩合反应）221 9.19The Mixed Aldol Condensation（混合醇醛缩合）222 9.20Commercial Syntheses via the Aldol Condensation （醇醛缩合反应在合成中的应用）223 10Carboxylic Acids and Their Derivatives （羧酸及其衍生物）230 10.1Nomenclature of Acids（羧酸的命名）231 10.2Physical Properties of Acids（羧酸的物理性质）234 10.3Acidity and Acidity Constants（酸性和酸度常数）235 10.4What Makes Carboxylic Acids Acidic?（羧酸的酸性基）236 10.5Effect of Structure on Acidity; the Inductive Effect Revisited （羧酸的结构对酸性的影响；诱导效应的影响）237 10.6Conversion of Acids to Salts（成盐反应）238 10.7Preparation of Acids（羧酸的制备）239 10.8Decarboxylation（脱羧反应）242 10.9Carboxylic Acid Derivatives（羧酸衍生物）242 10.10Esters（酯）242 10.11Preparation of Esters; Fischer Esterification （酯的制备；Fischer酯化反应）243 10.12The Mechanism of Acid-Catalyzed Esterification; Nucleophilic Acyl Substitution（酸催化酯化反应机制；酰基的亲核取代）244 10.13Lactones（内酯） 245 10.14Saponification of Esters（酯的皂化反应）246 10.15Ammonolysis of Esters（酯的氨解）246 10.16Reaction of Esters with Grignard Reagents （酯与格利雅试剂的反应）247 10.17Reduction of Esters（酯的还原）247 10.18The Need for Activated Acyl Compounds （酰基化合物活性的影响因素）248 10.19Acyl Halides（酰卤）248 10.20Acid Anhydrides（酸酐）250 10.21Amides（酰胺）252 10.22A Summary of Carboxylic Acid Derivatives（羧酸衍生物小结）253 10.23The a-Hydrogen of Esters; the Claisen Condensation （酯的a-氢；Claisen缩合）255 11Amines and Related Nitrogen Compounds（胺和相关含氮化合物）263 11.1Classification and Structure of Amines（胺的结构和分类）264 11.2Nomenclature of Amines（胺的命名）265 11.3Physical Properties and Intermolecular Interactions of Amines （胺的物理性质和分子间相互作用）266 11.4Preparation of Amines; Alkylation of Ammonia and Amines （胺的制备；氨和胺的烷基化）267 11.5Preparation of Amines; Reduction of Nitrogen Compounds （胺的制备；含氮化合物的还原）269 11.6The Basicity of Amines（胺的碱性）271 11.7Comparison of the Basicity and Acidity of Amines and Amides （胺和酰胺的酸碱性比较）273 11.8Reaction of Amines with Strong Acids; Amine Salts （胺与强酸的反应；胺盐）274 11.9Chiral Amines as Resolving Agents（手性胺作为拆分试剂）276 11.10Acylation of Amines with Acid Derivatives （胺与羧酸衍生物的酰化反应）276 11.11Quaternary Ammonium Compounds（季铵化合物）278 11.12Aromatic Diazonium Compounds（芳香重氮化合物）278 11.13Diazo Coupling; Azo Dyes（重氮偶联反应；偶氮染料）281 12Spectroscopy and Structure Determination（波谱学和结构测定）287 12.1Principles of Spectroscopy（波谱学原理）288 12.2Nuclear Magnetic Resonance Spectroscopy （核磁共振波谱）289 12.313C NMR Spectroscopy（13C NMR谱）297 12.4Infrared Spectroscopy（红外光谱）299 12.5Visible and Ultraviolet Spectroscopy（紫外-可见光谱）302 12.6Mass Spectrometry（质谱）304 13Heterocyclic Compounds（杂环化合物）315 13.1Pyridine： Bonding and Basicity（吡啶：结构和碱性）316 13.2Substitution in Pyridine（吡啶的取代反应）317 13.3Other Six-Membered Heterocycles（其他六元杂环）319 13.4Five-Membered Heterocycles： Furan, Pyrrole, and Thiophene （五元杂环：呋喃，吡咯和噻吩）322 13.5Electrophilic Substitution in Furan, Pyrrole, and Thiophene （呋喃，吡咯和噻吩的亲电取代反应）323 13.6Other Five-Membered Heterocycles： Azoles （其他五元杂环；唑类）324 13.7Fused-Ring Five-Membered Heterocycles： Indoles and Purines （稠环类五元杂环：吲哚和嘌呤）325 14Synthetic Polymers（合成高聚物）331 14.1Classification of Polymers（高聚物的分类）332 14.2Free-Radical Chain-Growth Polymerization（自由基链增长聚合）332 14.3Cationic Chain-Growth Polymerization（阳离子链增长聚合）336 14.4Anionic Chain-Growth Polymerization（阴离子链增长聚合）337 14.5Stereoregular Polymers; Ziegler-Natta Polymerization （有规立构高聚物；齐格勒-纳塔聚合）338 14.6Diene Polymers： Natural and Synthetic Rubber （二烯高聚物：天然橡胶和合成橡胶）339 14.7Copolymers（共聚物）341 14.8Step-Growth Polymerization： Dacron and Nylon （逐步增长聚合：涤纶和尼龙）342 14.9Other Step-Growth Polymers（其他逐步增长聚合物）344 15Lipids and Detergents（脂类和洗涤剂）350 15.1Fats and Oils; Triesters of Glycerol（油脂；甘油三酯）351 15.2Hydrogenation of Vegetable Oils（植物油的氢化反应）354 15.3Saponification of Fats and Oils; Soap （油脂的皂化反应；肥皂）354 15.4How Do Soaps Work?（肥皂如何去污？）355 15.5Synthetic Detergents Syndets（人工合成洗涤剂）356 15.6Phospholipids（磷脂）359 15.7Prostaglandins, Leukotrienes, and Lipoxins （前列腺素，白三烯和脂氧素）359 15.8Waxes（蜡）360 15.9Terpenes and Steroids（萜类和甾体化合物）361 16Carbohydrates（糖类）368 16.1Definitions and Classification（糖的定义和分类）369 16.2Monosaccharides（单糖）369 16.3Chirality in Monosaccharides; Fischer Projection Formulas and D, L-Sugars（单糖的手性；Fischer投影式和D,L-型糖）370 16.4The Cyclic Hemiacetal Structures of Monosaccharides （单糖的环状半缩醛结构）373 16.5Anomeric Carbons; Mutarotation（异头碳；变旋光现象）375 16.6Pyranose and Furanose Structures（吡喃糖和呋喃糖的结构）376 16.7Conformations of Pyranoses（吡喃糖的构象）377 16.8Esters and Ethers from Monosaccharides （单糖的成酯和成醚反应）378 16.9Reduction of Monosaccharides（单糖的还原）379 16.10Oxidation of Monosaccharides（单糖的氧化）379 16.11Formation of Glycosides from Monosaccharides （单糖的成苷反应）380 16.12Disaccharides（双糖）382 16.13Polysaccharides（多糖）385 16.14Sugar Phosphates（糖的磷酸酯）388 16.15Deoxy Sugars（脱氧糖）388 16.16Amino Sugars（氨基糖）389 16.17Ascorbic Acid Vitamin C［抗坏血酸（维生素C）］389 17Amino Acids, Peptides, and Proteins （氨基酸，肽和蛋白质）394 17.1Naturally Occurring Amino Acids（天然氨基酸）395 17.2The Acid-Base Properties of Amino Acids（氨基酸的酸碱性）397 17.3The Acid-Base Properties of Amino Acids with More Than One Acidic or Basic Group（含有多个酸性或碱性基团氨基酸的酸碱性）399 17.4Electrophoresis（电泳）401 17.5Reactions of Amino Acids（氨基酸的反应）401 17.6The Ninhydrin Reaction（茚三酮反应）402 17.7Peptides（肽）402 17.8The Disulfide Bond（二硫键）404 17.9Proteins（蛋白质）404 17.10The Primary Structure of Proteins（蛋白质的一级结构）404 17.11The Logic of Sequence Determination （序列测定的推理方法）408 17.12Secondary Structure of Proteins（蛋白质的二级结构）409 17.13Tertiary Structure： Fibrous and Globular Proteins（三级结构：纤维蛋白和球蛋白）410 17.14Quaternary Protein Structure（蛋白质的四级结构）413 18Nucleotides and Nucleic Acids（核苷酸和核酸）419 18.1The General Structure of Nucleic Acids（核酸的一般结构）420 18.2Components of Deoxyribonucleic Acid DNA （脱氧核糖核酸的组成）420 18.3Nucleosides（核苷）421 18.4Nucleotides（核苷酸）422 18.5The Primary Structure of DNA（DNA的一级结构）424 18.6Sequencing Nucleic Acids（核酸的测序）424 18.7Secondary DNA Structure; the Double Helix （DNA的二级结构；双螺旋结构）425 18.8DNA Replication（DNA复制）427 18.9Ribonucleic Acids; RNA（核糖核酸；RNA）428 18.10The Genetic Code and Protein Biosynthesis （遗传密码和蛋白质的生物合成）429 18.11Other Biologically Important Nucleotides （生物学上其他的重要核苷酸）431
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《Organic Chemistry：A Brief Course》是供临床医学、生物学、药学等学科相关专业使用的有机化学本科英语教材，其内容表述规范，可读性强。该教材与我国供基础、临床、预防、口腔医学等专业使用的卫生部“十二五”规划教材《有机化学》的知识体系及教学内容接近，符合我国医学学科相关专业有机化学教学的基本要求，可用于我国高等学校医学相关专业有机化学的双语教学。 为了使本教材更适合我国医学学科相关专业的有机化学教学，化学工业出版社组织国内五所高等院校10位富有有机化学教学经验的教师，以该教材的第13版为蓝本，在尊重原教材版权的基础上，对该教材进行了改编。改编版本既充分体现原书特点，又更适用于我国的读者。改编重点为：第3章、第7~10章增加了若干知识点，第14章删减了部分内容。为使教材更加精炼紧凑，改编教材还删除了原书的静电势能图、部分球棍模型图、“A Word About…”小短文以及索引等内容。全书调整了部分内容的陈述顺序、章节标题，添加了专业术语的中文译注，增删了部分习题。改编后，教材内容具有更好的系统性、完整性和可读性。该教材改编后，除了可用作相关专业有机化学双语教学的教材外，也可供非双语教学的师生及其他科技工作者用作学习有机化学的参考书。 该教材的改编由上海交通大学医学院的陆阳、杨丽敏负责统稿。参加改编的教师有上海交通大学医学院陆阳、杨丽敏、林琦，山东大学郭今心，中南大学罗一鸣，大连医科大学贺欣、徐乃进，南华大学邓健、孙允凯、聂长明。由于水平有限，该教材的改编难免有不妥之处，敬请广大师生及其他读者批评指正。 编者 2013年6月25日于上海
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