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1 绪论Introduction1

1.1 有机化学的产生和发展The Origin and Development of Organic Chemistry1

1.1.1 有机化学的产生The Origin of Organic Chemistry1

1.1.2 有机化学的发展The Development of Organic Chemistry2

1.2 有机化合物的特性Characteristics of Organic Compounds3

1.2.1 数量庞大和结构复杂Enormous Quantities and Complicated Structures4

1.2.2 热稳定性差和容易燃烧Thermally Unstability and Inflammability4

1.2.3 熔点和沸点低Low-melting and Low-boiling4

1.2.4 难溶于水Weak Solubility in Water4

1.2.5 化学反应速度慢Slow Reaction Rates4

1.2.6 反应产物复杂Complicated Products5

科苑拾贝 现代武器装备与有机材料5

1.3 有机化合物中的共价键Covalent Bonds in Organic Compounds6

1.3.1 碳原子的杂化与成键方式Hybridization and Bonding Models of Carbon Atom6

1.3.2 共价键的类型Types of Covalent Bonds7

1.3.3 共价键的性质Characteristics of Covalent Bonds7

1.4 共价键的断裂方式C1eavage Methods of Covalent Bonds9

1.4.1 均裂Homolytic Cleavage9

科苑拾贝 吸烟与自由基——吸烟有害健康10

1.4.2 异裂Heterolytic Cleavage10

1.5 有机化合物构造式的表示方法Decription Methods of Organic Compounds Structures11

1.5.1 平面投影式Arachnoids Formula11

1.5.2 折线式Linear Formula11

1.6 有机化学中的酸碱概念Acid-Base Concepts in Organic Chemistry12

1.6.1 Br？nsted酸碱质子理论Br？nsted Acid-Base Concept12

1.6.2 Lewis酸碱电子理论Lewis Acid-Base Concept13

1.7 有机化合物的分类Classification of Organic Compounds13

1.7.1 按碳架分类Classification by Carbon Skeletons13

1.7.2 按官能团分类Classification by Functional Groups14

1.8 研究有机化合物的一般程序和方法Common Procedures and Methods of Researching Organic Compounds16

1.8.1 分离提纯Separation Purification16

1.8.2 元素的定性定量Qualitative and Quantitative Determinations of Elements16

1.8.3 分子质量的测定Molecular Weight Tests17

1.8.4 结构式的确定Structural Formula Determinations17

1.9 有机化学与农业科学的关系Relationships of Organic Chemistry and Agricultural Science17

科苑拾贝 新世纪的“绿色纤维”18

习题19

2 饱和烃Saturated Hydrocarbon21

2.1 烷烃A1kane21

2.1.1 烷烃的命名Nomenclature of Alkanes22

2.1.2 烷烃的分子结构Structures of Alkanes25

2.1.3 烷烃的物理性质Physical Properties of Alkanes30

2.1.4 烷烃的化学性质Chemical Properties of Alkanes32

2.2 环烷烃Cycloalkane35

2.2.1 环烷烃的分类、异构和命名Classification,Isomerism and Nomenclature of Cycloalkanes35

2.2.2 环烷烃的物理性质Physical Properties of Cycloalkanes38

2.2.3 环烷烃的化学性质Chemical Properties of Cycloalkanes38

2.2.4 环烷烃的分子结构Structures of Cycloalkanes40

科苑拾贝 天然气、石油、沼气及动植物体内的烷烃46

习题47

3 不饱和烃Unsaturated Hydrocarbon50

3.1 烯烃Alkene50

3.1.1 烯烃的结构Structures of Alkenes50

3.1.2 烯烃的命名Nomenclature of Alkenes53

3.1.3 烯烃的物理性质Physical Properties of Alkenes54

3.1.4 烯烃的化学性质Chemical Properties of Alkenes55

科苑拾贝 乙烯与丙烯66

3.2 二烯烃Diene67

3.2.1 二烯烃的分类和命名Classification and Nomenclature of Dienes67

3.2.2 共轭二烯烃的结构和共轭效应Structures and Conjugative Effects of Conjugated Dienes68

3.2.3 共轭二烯烃的化学性质Chemical Properties of Conjugated Dienes71

3.2.4 萜类化合物Terpene73

科苑拾贝 烯烃化学发展史79

3.3 炔烃Alkynes79

3.3.1 炔烃的分子结构Molecular Structures of Alkynes79

3.3.2 炔烃的异构和命名Isomerism and Nomenclature of Alkynes81

3.3.3 炔烃的物理性质Physical Properties of Alkynes81

3.3.4 炔烃的化学性质Chemical Properties of Alkynes82

习题86

4 芳香烃Aromatic Hydrocarbon90

4.1 芳香烃的分类Classification of Aromatic Hydrocarbons90

4.1.1 单环芳烃Monocyclic Aromatic Hydrocarbons90

4.1.2 多环芳烃Polycyclic Aromatic Hydrocarbons91

4.1.3 非苯芳烃Non-Benzenoid Aromatic Hydrocarbons91

4.2 单环芳烃的结构和命名Structures and Nomenclature of Monocyclic Aromatic Hydrocarbons92

4.2.1 苯的结构The Structure of Benzene92

4.2.2 单环芳烃的异构现象Isomerism of Monocyclic Aromatic Hydrocarbons95

4.2.3 单环芳烃及其衍生物的命名Nomenclature of Monocyclic Aromatic Hydrocarbons and their Derivatives95

4.3 单环芳烃的性质Properties of Monocyclic Aromatic Hydrocarbons98

4.3.1 单环芳烃的物理性质Physical Properties of Monocyclic Aromatic Hydrocarbons98

4.3.2 单环芳烃的化学性质Chemical Properties of Monocyclic Aromatic Hydrocarbons98

4.4 苯环上取代基的定位规律Locating Regularity of Substituent on Benzene105

4.4.1 一元取代苯的定位规律和定位基的分类Locating Regularity of Monosubstitutive Benzene and Classification of Locating Groups105

4.4.2 定位规律的理论解释Theoretical Explanations of Locating Regularity108

4.4.3 二元取代苯的定位规则Locating Rule of Disubstitutive Benzene110

4.4.4 定位规律的应用Application of Locating Regularity111

科苑拾贝 苯——隐藏在家中的敌人112

4.5 稠环芳烃Fused-Ring Aromatic Hydrocarbons112

4.5.1 萘、蒽、菲的结构和命名Structures and Nomenclature of Naphthalene,Anthracene and Phenanthrene112

4.5.2 萘的性质Properties of Naphthalene114

4.5.3 蒽和菲的性质Properties of Anthracene and Phenanthrene115

4.5.4 其他稠环芳烃Other Fused-Ring Aromatic Hydrocarbons116

4.6 非苯芳香烃及Hückel规则Non-Benzenoid Aromatics and Their Hückel's Rule116

科苑拾贝 二噁英对人类的危害117

习题118

5 卤代烃Halohydrocarbon121

5.1 卤代烃的分类和命名Classification and Nomenclature of Alkyl Halides121

5.1.1 卤代烃的分类Classification of Alkyl Halides121

5.1.2 卤代烃的命名Nomenclature of Alkyl Halides122

5.2 卤代烷Alkyl Halide124

5.2.1 卤代烷的物理性质Physical Properties of Alkyl Halides124

5.2.2 卤代烷的化学性质Chemical Properties of Alkyl Halides125

5.2.3 亲核取代反应历程The Mechanism of Substitution Reactions128

5.2.4 消除反应历程The Mechanism of Elimination Reactions132

5.3 卤代烯烃和卤代芳烃Alkenyl Halide and Aryl Halide135

5.3.1 卤代烯烃和卤代芳烃的化学反应Chemical Reactions of Alkenyl Halides and Aryl Halides136

5.3.2 卤代烯烃和卤代芳烃的化学活性Chemical Activities of Alkenyl Halides and Aryl Halides138

5.4 重要的卤代烃Important Halohydrocarbons140

5.4.1 DDT 4,4′-dichloro-diphenyl-trichloroethane140

5.4.2 杀螨酯4,4′-dichloro-diphenyl-ethylene monoacetate140

5.4.3 三氯杀虫酯2,2,2-trichloro-1-(3,4-dichlorophenyl)acetate140

5.4.4 三氯甲烷Chloroform141

5.4.5 四氯化碳Carbon Tetrachloride141

5.4.6 聚四氟乙烯Poly(tetrafluoroethylene)141

科苑拾贝 氟氯烃的功与过142

习题143

6 旋光异构Optical Isomerism147

6.1 物质的旋光性Optical Activities of Substances148

6.1.1 偏振光Polarized Light148

6.1.2 旋光度Optical Rotation149

6.1.3 比旋光度Specific Rotation150

6.2 物质的旋光性与分子结构的关系The Relationship of the Optical Activity and the Structure of a Molecule151

6.2.1 手性、手性碳原子和手性分子Chirality,Chiral Carbon Atom and Chiral Molecule151

6.2.2 手性与对称因素的关系The Relationship of Chirality and Symmetry152

6.3 含有一个手性碳原子化合物的旋光异构Optical Isomerism of Compounds Containing One Chiral Atom154

6.3.1 对映体Enantiomers154

6.3.2 外消旋体Raceme154

6.3.3 Fischer投影式Fischer Projection155

6.3.4 外消旋体的拆分Resolution of Raceme156

6.4 旋光异构体构型的表示法Nomenclature of Enantiomers157

6.4.1 D,L标记法The D,L Convention157

6.4.2 R,S标记法The R,S Convention158

6.5 含有两个手性碳原子化合物的旋光异构Optical Isomerism of Compounds Containing Two Chiral Atoms160

6.5.1 含有两个不相同手性碳原子的化合物Compounds Containing Two Different Chiral Carbon Atoms160

6.5.2 含有两个相同手性碳原子的化合物Compounds Containing Two Identical Chiral Carbon Atoms161

6.5.3 其他立体异构现象Other Stereoisomerisms162

科苑拾贝 手性化合物与农药和药物164

6.6 某些有机反应中的立体化学Stereoisomerisms of Some Organic Reactions164

6.6.1 SN2反应的立体化学Stereochemistry of the SN2 Reaction165

6.6.2 亲电加成反应的立体化学Stereochemistry of the Electrophilic Reaction165

6.6.3 E2反应的立体化学Stereochemistry of the E2 Reaction167

习题168

7 醇、酚、醚Alcohol,Phenol and Ether170

7.1 醇Alcohol170

7.1.1 醇的分类和命名Classification and Nomenclature of Alcohols170

7.1.2 醇的物理性质Physical Properties of Alcohols172

7.1.3 醇的化学性质Chemical Properties of Alcohols174

科苑拾贝 绿色能源——乙醇、甲醇180

7.2 酚Phenol180

7.2.1 酚的分类和命名Classification and Nomenclature of Phenols180

7.2.2 酚的结构Structures of Phenols181

7.2.3 酚的物理性质Physical Properties of Phenols182

7.2.4 酚的化学性质Chemical Properties of Phenols183

科苑拾贝 维生素E187

7.3 醚Ether188

7.3.1 醚的分类和命名Classification and Nomenclature of Ethers188

7.3.2 醚的物理性质Physical Properties of Ethers189

7.3.3 醚的化学性质Chemical Properties of Ethers190

7.3.4 环醚Cyclic Ether191

科苑拾贝 新一代绿色能源——二甲醚（DME）193

习题194

8 醛、酮、醌Aldehyde,Ketone,Quinone198

8.1 醛和酮Aldehydes and Ketone198

8.1.1 醛和酮的分类和命名Classification and Nomenclature of Aldehydes and Ketones198

8.1.2 醛和酮的物理性质Physical Properties of Aldehydes and Ketones199

8.1.3 醛和酮的结构Structures of Aldehydes and Ketones200

8.1.4 醛和酮的化学性质Chemical Properties of Aldehydes and Ketones201

科苑拾贝 甲醛的用途及危害209

8.2 醌Quinones209

8.2.1 醌的结构和命名Structures and Nomenclature of Quinones209

8.2.2 醌的化学性质Chemical Properties of Quinones210

科苑拾贝 醌类化合物211

习题212

9 羧酸和取代酸Carboxylic Acid and Substituted Acid216

9.1 羧酸Carboxylic Acid216

9.1.1 羧酸的分类和命名Classification and Nomenclature of Carboxylic Acids216

9.1.2 羧酸的结构Structures of Carboxylic Acids218

9.1.3 羧酸的物理性质Physical Properties of Carboxylic Acids219

9.1.4 羧酸的化学性质Chemical Properties of Carboxylic Acids221

9.1.5 个别化合物Typical Compounds225

科苑拾贝 食品添加剂——山梨酸228

9.2 羧酸衍生物Carboxylic Acid Derivatives229

9.2.1 羧酸衍生物的命名Nomenclature of Carboxylic Acid Derivatives229

9.2.2 羧酸衍生物的物理性质Physical Properties of Carboxylic Acid Derivatives230

9.2.3 羧酸衍生物的化学性质Chemical Properties of Carboxylic Acid Derivatives230

9.2.4 酯化和酯水解的反应历程Esterifications and the Mechanism for Hydrolysis of Esters232

9.2.5 个别化合物Typical Compounds233

9.3 取代酸Substituted Acid235

9.3.1 羟基酸Hydroxy Acid235

9.3.2 羰基酸（氧代酸）Carbonyl Acid242

科苑拾贝 家庭酸奶的制备248

习题248

10 含氮有机化合物Nitrogenous Organic Compounds252

10.1 胺Amine253

10.1.1 胺的分类和命名Classifications and Nomenclature of Amines253

10.1.2 胺的结构Structures of Amines255

10.1.3 胺的物理性质Physical Properties of Amines256

10.1.4 胺的化学性质Chemical Properties of Amines257

科苑拾贝 珍惜生命远离毒品——冰毒264

10.1.5 个别化合物Typical Compounds265

10.2 酰胺Amide266

10.2.1 酰胺的分类和命名Classifications and Nomenclature of Amides266

10.2.2 酰胺的结构Structures of Amides267

10.2.3 酰胺的物理性质Physical Properties of Amides268

10.2.4 酰胺的化学性质Chemical Properties of Amides269

10.2.5 碳酸的酰胺Amides of Carbonic Acids271

10.2.6 苯磺酰胺Benzenesulfonamide273

10.3 硝基化合物Nitro Compounds274

10.3.1 分类和命名Classification and Nomenclature274

10.3.2 硝基化合物的结构Structures of Nitro Compounds274

10.3.3 物理性质Physical Properties274

10.3.4 化学性质Chemical Properties275

习题276

11 含硫、含磷有机化合物Sulfurated,Phosphorated Organic Compounds280

11.1 含硫有机化合物Sulfurated Organic Compounds280

11.1.1 含硫有机化合物的分类和命名Classification and Nomenclature of Sulfurated Organic Compounds280

11.1.2 硫醇和硫酚Thiol and Thiophenol282

11.1.3 硫醚Thioether284

11.1.4 有机硫杀菌剂Organosulfur Compounds Fungicides285

11.2 含磷有机化合物Phosphorated Organic Compounds286

11.2.1 含磷有机化合物的分类和命名Classification and Nomenclature of Phosphorated Organic Compounds286

11.2.2 膦酸和膦酸酯类化合物Phosphonic Acids and Phosphonate Esters287

11.2.3 磷酸酯和硫代磷酸酯Phosphonate Esters and Thiophosphonate Esters288

科苑拾贝 有机磷农药的利与弊289

习题290

12 杂环化合物及生物碱Heterocyclic Compounds and Natural Base292

12.1 杂环化合物Heterocyclic Compounds292

12.1.1 杂环化合物的分类和命名Classification and Nomenclature of Heterocyclic Compounds293

12.1.2 杂环化合物的结构与芳香性Structures and Aromaticity of Heterocyclic Compounds294

12.1.3 杂环化合物的化学性质Chemical Properties of Heterocyclic Compounds296

12.1.4 杂环化合物及其衍生物选述Selected Introduction of Heterocyclic Compounds and Their Derivatives299

12.2 生物碱Natural Base310

12.2.1 生物碱概述Introduction of Natural Bases310

12.2.2 生物碱的一般性质General Properties of Natural Bases310

12.2.3 生物碱的一般提取方法General Extraction Methods of Natural Bases311

12.2.4 个别化合物Typical Natural Bases311

科苑拾贝 鸦片与海洛因314

习题314

13 碳水化合物Carbohydrate316

13.1 单糖Monosaccharide316

13.1.1 单糖的分类Classification of Monosaccharides316

13.1.2 单糖的构型Configuration of Monosaccharides318

13.1.3 单糖的结构Structures of Monosaccharides319

13.1.4 单糖的物理性质Physical Properties of Monosaccharides324

13.1.5 单糖的化学性质Chemical Properties of Monosaccharides325

13.1.6 重要的单糖和糖的衍生物Important Monosaccharides and Derivatives of Monosaccharides333

13.2 二糖Disaccharide335

13.2.1 还原性二糖Reducing Disaccharide335

13.2.2 非还原性二糖Non-reducing Disaccharides337

13.3 多糖Polysaccharide338

13.3.1 均多糖Homopolysaccharide339

13.3.2 杂多糖Heteropo1ysaccharide346

科苑拾贝 尼龙的人工合成348

习题349

14 蛋白质和核酸Protein and Nucleic Acid354

14.1 氨基酸Amino Acid354

14.1.1 氨基酸的分类和结构Classification and Structures of Amino Acids354

14.1.2 氨基酸的物理性质Physical Properties of Amino Acids357

14.1.3 氨基酸的化学性质Chemical Properties of Amino Acids358

科苑拾贝 采用微生物方法将石油人工转化成为氨基酸363

14.2 蛋白质Protein364

14.2.1 蛋白质的组成和分类Composition and Classification of Proteins364

14.2.2 蛋白质的结构Structures of Proteins365

14.2.3 蛋白质的理化性质Physical and Chemical Properties of Proteins368

科苑拾贝 天然药物中的毒蛋白和多肽372

14.3 核酸Nucleic Acid372

14.3.1 核酸的组成Composition of Nucleic Acids373

14.3.2 核苷Nucleoside373

14.3.3 核苷酸和脱氧核苷酸Nucleotides and Deoxynucleotides375

14.3.4 核酸的结构Structures of Nucleic Acids376

14.3.5 核酸的理化性质Physical and Chemical Properties of Nucleic Acids379

科苑拾贝 癌症与抗癌新药物的研究380

习题381

15 油脂和类脂Neutral Fats and Lipids384

15.1 油脂Oil384

15.1.1 油脂的组成与结构Composition and Structures of Oil384

15.1.2 油脂的理化性质Physical and Chemical Properties of Oil386

15.1.3 肥皂和表面活性剂Soap and Surfactant390

科苑拾贝 家用洗涤剂（粉）392

15.2 类脂Lipids393

15.2.1 蜡Wax393

15.2.2 磷脂Phospholipids394

15.2.3 甾族化合物Steroid397

习题401

16 有机化合物的波谱知识Spectroscopy Knowledge of Organic Compounds402

16.1 电磁波谱的一般概念General Concepts of Electromagnetic Spectrum402

16.1.1 转动光谱Rotation Spectrum403

16.1.2 振动光谱Vibration Spectrum403

16.1.3 电子光谱Electronic Spectrum404

16.2 紫外光谱Ultraviolet Spectrum404

16.2.1 电子跃迁类型Types of Electronic Transition404

16.2.2 紫外光谱图Ultraviolet Spectrogram405

16.2.3 紫外光谱图与分子结构的关系Relationships of Ultraviolet Spectrograms and Molecular Structures406

16.2.4 紫外光谱的应用Application of Ultraviolet Spectrum407

16.3 红外光谱Infrared Spectrum407

16.3.1 分子振动和红外光谱Molecular Vibration and Infrared Spectrum407

16.3.2 有机物官能团的红外光谱The Infrared Spectra of the Organic Functional Group409

16.4 核磁共振谱Nuclear Magnetic Resonance Spectrum411

16.4.1 基本知识Basic Knowledge412

16.4.2 化学位移Chemical Shift413

16.4.3 自旋偶合与自旋裂分Spin Coupling and Spin Splitting415

16.4.4 核磁共振谱的应用Application of Nuclear Magnetic Resonance Spectra417

16.5 质谱Mass Spectrum417

科苑拾贝 近红外光谱技术的应用421

习题421

17 网络导航Network Navigation424

17.1 开航前的话Before Sailing424

17.2 从网上查出所需化学数据Chemical Datum from WWW424

17.3 化学网站Chemical Links426

17.4 文献检索Literature Searching429

17.5 有机化学网站Organic Chemical Web430

17.6 检索科技论文Searching of Science and Technology Thesises432

17.7 生命科学的最新进展Advanced Developments of Life Sciences434

习题435

附录 有机化合物英文命名简介436

主要参考文献452