1 绪论Introduction 1
1.1 有机化学的产生和发展The Origin and Development of Organic Chemistry 1
1.1.1 有机化学的产生The Origin of Organic Chemistry 1
1.1.2 有机化学的发展The Development of Organic Chemistry 2
1.2 有机化合物的特性Characteristics of Organic Compounds 3
1.2.1 数量庞大和结构复杂Enormous Quantities and Complicated Structures 4
1.2.2 热稳定性差和容易燃烧Thermally Unstability and Inflammability 4
1.2.3 熔点和沸点低Low-melting and Low-boiling 4
1.2.4 难溶于水Weak Solubility in Water 4
1.2.5 化学反应速度慢Slow Reaction Rates 4
1.2.6 反应产物复杂Complicated Products 5
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 Compounds 6
1.3.1 碳原子的杂化与成键方式Hybridization and Bonding Models of Carbon Atom 6
1.3.2 共价键的类型Types of Covalent Bonds 7
1.3.3 共价键的性质Characteristics of Covalent Bonds 7
1.4 共价键的断裂方式C1eavage Methods of Covalent Bonds 9
1.4.1 均裂Homolytic Cleavage 9
科苑拾贝 吸烟与自由基——吸烟有害健康 10
1.4.2 异裂Heterolytic Cleavage 10
1.5 有机化合物构造式的表示方法Decription Methods of Organic Compounds Structures 11
1.5.1 平面投影式Arachnoids Formula 11
1.5.2 折线式Linear Formula 11
1.6 有机化学中的酸碱概念Acid-Base Concepts in Organic Chemistry 12
1.6.1 Br？nsted酸碱质子理论Br？nsted Acid-Base Concept 12
1.6.2 Lewis酸碱电子理论Lewis Acid-Base Concept 13
1.7 有机化合物的分类Classification of Organic Compounds 13
1.7.1 按碳架分类Classification by Carbon Skeletons 13
1.7.2 按官能团分类Classification by Functional Groups 14
1.8 研究有机化合物的一般程序和方法Common Procedures and Methods of Researching Organic Compounds 16
1.8.1 分离提纯Separation Purification 16
1.8.2 元素的定性定量Qualitative and Quantitative Determinations of Elements 16
1.8.3 分子质量的测定Molecular Weight Tests 17
1.8.4 结构式的确定Structural Formula Determinations 17
1.9 有机化学与农业科学的关系Relationships of Organic Chemistry and Agricultural Science 17
科苑拾贝 新世纪的“绿色纤维” 18
习题 19
2 饱和烃Saturated Hydrocarbon 21
2.1 烷烃A1kane 21
2.1.1 烷烃的命名Nomenclature of Alkanes 22
2.1.2 烷烃的分子结构Structures of Alkanes 25
2.1.3 烷烃的物理性质Physical Properties of Alkanes 30
2.1.4 烷烃的化学性质Chemical Properties of Alkanes 32
2.2 环烷烃Cycloalkane 35
2.2.1 环烷烃的分类、异构和命名Classification,Isomerism and Nomenclature of Cycloalkanes 35
2.2.2 环烷烃的物理性质Physical Properties of Cycloalkanes 38
2.2.3 环烷烃的化学性质Chemical Properties of Cycloalkanes 38
2.2.4 环烷烃的分子结构Structures of Cycloalkanes 40
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 Hydrocarbon 50
3.1 烯烃Alkene 50
3.1.1 烯烃的结构Structures of Alkenes 50
3.1.2 烯烃的命名Nomenclature of Alkenes 53
3.1.3 烯烃的物理性质Physical Properties of Alkenes 54
3.1.4 烯烃的化学性质Chemical Properties of Alkenes 55
科苑拾贝 乙烯与丙烯 66
3.2 二烯烃Diene 67
3.2.1 二烯烃的分类和命名Classification and Nomenclature of Dienes 67
3.2.2 共轭二烯烃的结构和共轭效应Structures and Conjugative Effects of Conjugated Dienes 68
3.2.3 共轭二烯烃的化学性质Chemical Properties of Conjugated Dienes 71
3.2.4 萜类化合物Terpene 73
科苑拾贝 烯烃化学发展史 79
3.3 炔烃Alkynes 79
3.3.1 炔烃的分子结构Molecular Structures of Alkynes 79
3.3.2 炔烃的异构和命名Isomerism and Nomenclature of Alkynes 81
3.3.3 炔烃的物理性质Physical Properties of Alkynes 81
3.3.4 炔烃的化学性质Chemical Properties of Alkynes 82
习题 86
4 芳香烃Aromatic Hydrocarbon 90
4.1 芳香烃的分类Classification of Aromatic Hydrocarbons 90
4.1.1 单环芳烃Monocyclic Aromatic Hydrocarbons 90
4.1.2 多环芳烃Polycyclic Aromatic Hydrocarbons 91
4.1.3 非苯芳烃Non-Benzenoid Aromatic Hydrocarbons 91
4.2 单环芳烃的结构和命名Structures and Nomenclature of Monocyclic Aromatic Hydrocarbons 92
4.2.1 苯的结构The Structure of Benzene 92
4.2.2 单环芳烃的异构现象Isomerism of Monocyclic Aromatic Hydrocarbons 95
4.2.3 单环芳烃及其衍生物的命名Nomenclature of Monocyclic Aromatic Hydrocarbons and their Derivatives 95
4.3 单环芳烃的性质Properties of Monocyclic Aromatic Hydrocarbons 98
4.3.1 单环芳烃的物理性质Physical Properties of Monocyclic Aromatic Hydrocarbons 98
4.3.2 单环芳烃的化学性质Chemical Properties of Monocyclic Aromatic Hydrocarbons 98
4.4 苯环上取代基的定位规律Locating Regularity of Substituent on Benzene 105
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 Groups 105
4.4.2 定位规律的理论解释Theoretical Explanations of Locating Regularity 108
4.4.3 二元取代苯的定位规则Locating Rule of Disubstitutive Benzene 110
4.4.4 定位规律的应用Application of Locating Regularity 111
科苑拾贝 苯——隐藏在家中的敌人 112
4.5 稠环芳烃Fused-Ring Aromatic Hydrocarbons 112
4.5.1 萘、蒽、菲的结构和命名Structures and Nomenclature of Naphthalene,Anthracene and Phenanthrene 112
4.5.2 萘的性质Properties of Naphthalene 114
4.5.3 蒽和菲的性质Properties of Anthracene and Phenanthrene 115
4.5.4 其他稠环芳烃Other Fused-Ring Aromatic Hydrocarbons 116
4.6 非苯芳香烃及Hückel规则Non-Benzenoid Aromatics and Their Hückel's Rule 116
科苑拾贝 二噁英对人类的危害 117
习题 118
5 卤代烃Halohydrocarbon 121
5.1 卤代烃的分类和命名Classification and Nomenclature of Alkyl Halides 121
5.1.1 卤代烃的分类Classification of Alkyl Halides 121
5.1.2 卤代烃的命名Nomenclature of Alkyl Halides 122
5.2 卤代烷Alkyl Halide 124
5.2.1 卤代烷的物理性质Physical Properties of Alkyl Halides 124
5.2.2 卤代烷的化学性质Chemical Properties of Alkyl Halides 125
5.2.3 亲核取代反应历程The Mechanism of Substitution Reactions 128
5.2.4 消除反应历程The Mechanism of Elimination Reactions 132
5.3 卤代烯烃和卤代芳烃Alkenyl Halide and Aryl Halide 135
5.3.1 卤代烯烃和卤代芳烃的化学反应Chemical Reactions of Alkenyl Halides and Aryl Halides 136
5.3.2 卤代烯烃和卤代芳烃的化学活性Chemical Activities of Alkenyl Halides and Aryl Halides 138
5.4 重要的卤代烃Important Halohydrocarbons 140
5.4.1 DDT 4,4′-dichloro-diphenyl-trichloroethane 140
5.4.2 杀螨酯4,4′-dichloro-diphenyl-ethylene monoacetate 140
5.4.3 三氯杀虫酯2,2,2-trichloro-1-(3,4-dichlorophenyl)acetate 140
5.4.4 三氯甲烷Chloroform 141
5.4.5 四氯化碳Carbon Tetrachloride 141
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 Isomerism 147
6.1 物质的旋光性Optical Activities of Substances 148
6.1.1 偏振光Polarized Light 148
6.1.2 旋光度Optical Rotation 149
6.1.3 比旋光度Specific Rotation 150
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 Molecule 151
6.2.1 手性、手性碳原子和手性分子Chirality,Chiral Carbon Atom and Chiral Molecule 151
6.2.2 手性与对称因素的关系The Relationship of Chirality and Symmetry 152
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 Atom 154
6.3.1 对映体Enantiomers 154
6.3.2 外消旋体Raceme 154
6.3.3 Fischer投影式Fischer Projection 155
6.3.4 外消旋体的拆分Resolution of Raceme 156
6.4 旋光异构体构型的表示法Nomenclature of Enantiomers 157
6.4.1 D,L标记法The D,L Convention 157
6.4.2 R,S标记法The R,S Convention 158
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 Atoms 160
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 Atoms 160
6.5.2 含有两个相同手性碳原子的化合物Compounds Containing Two Identical Chiral Carbon Atoms 161
6.5.3 其他立体异构现象Other Stereoisomerisms 162
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 Reactions 164
6.6.1 SN2反应的立体化学Stereochemistry of the SN2 Reaction 165
6.6.2 亲电加成反应的立体化学Stereochemistry of the Electrophilic Reaction 165
6.6.3 E2反应的立体化学Stereochemistry of the E2 Reaction 167
习题 168
7 醇、酚、醚Alcohol,Phenol and Ether 170
7.1 醇Alcohol 170
7.1.1 醇的分类和命名Classification and Nomenclature of Alcohols 170
7.1.2 醇的物理性质Physical Properties of Alcohols 172
7.1.3 醇的化学性质Chemical Properties of Alcohols 174
科苑拾贝 绿色能源——乙醇、甲醇 180
7.2 酚Phenol 180
7.2.1 酚的分类和命名Classification and Nomenclature of Phenols 180
7.2.2 酚的结构Structures of Phenols 181
7.2.3 酚的物理性质Physical Properties of Phenols 182
7.2.4 酚的化学性质Chemical Properties of Phenols 183
科苑拾贝 维生素E 187
7.3 醚Ether 188
7.3.1 醚的分类和命名Classification and Nomenclature of Ethers 188
7.3.2 醚的物理性质Physical Properties of Ethers 189
7.3.3 醚的化学性质Chemical Properties of Ethers 190
7.3.4 环醚Cyclic Ether 191
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,Quinone 198
8.1 醛和酮Aldehydes and Ketone 198
8.1.1 醛和酮的分类和命名Classification and Nomenclature of Aldehydes and Ketones 198
8.1.2 醛和酮的物理性质Physical Properties of Aldehydes and Ketones 199
8.1.3 醛和酮的结构Structures of Aldehydes and Ketones 200
8.1.4 醛和酮的化学性质Chemical Properties of Aldehydes and Ketones 201
科苑拾贝 甲醛的用途及危害 209
8.2 醌Quinones 209
8.2.1 醌的结构和命名Structures and Nomenclature of Quinones 209
8.2.2 醌的化学性质Chemical Properties of Quinones 210
科苑拾贝 醌类化合物 211
习题 212
9 羧酸和取代酸Carboxylic Acid and Substituted Acid 216
9.1 羧酸Carboxylic Acid 216
9.1.1 羧酸的分类和命名Classification and Nomenclature of Carboxylic Acids 216
9.1.2 羧酸的结构Structures of Carboxylic Acids 218
9.1.3 羧酸的物理性质Physical Properties of Carboxylic Acids 219
9.1.4 羧酸的化学性质Chemical Properties of Carboxylic Acids 221
9.1.5 个别化合物Typical Compounds 225
科苑拾贝 食品添加剂——山梨酸 228
9.2 羧酸衍生物Carboxylic Acid Derivatives 229
9.2.1 羧酸衍生物的命名Nomenclature of Carboxylic Acid Derivatives 229
9.2.2 羧酸衍生物的物理性质Physical Properties of Carboxylic Acid Derivatives 230
9.2.3 羧酸衍生物的化学性质Chemical Properties of Carboxylic Acid Derivatives 230
9.2.4 酯化和酯水解的反应历程Esterifications and the Mechanism for Hydrolysis of Esters 232
9.2.5 个别化合物Typical Compounds 233
9.3 取代酸Substituted Acid 235
9.3.1 羟基酸Hydroxy Acid 235
9.3.2 羰基酸（氧代酸）Carbonyl Acid 242
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 Compounds 252
10.1 胺Amine 253
10.1.1 胺的分类和命名Classifications and Nomenclature of Amines 253
10.1.2 胺的结构Structures of Amines 255
10.1.3 胺的物理性质Physical Properties of Amines 256
10.1.4 胺的化学性质Chemical Properties of Amines 257
科苑拾贝 珍惜生命远离毒品——冰毒 264
10.1.5 个别化合物Typical Compounds 265
10.2 酰胺Amide 266
10.2.1 酰胺的分类和命名Classifications and Nomenclature of Amides 266
10.2.2 酰胺的结构Structures of Amides 267
10.2.3 酰胺的物理性质Physical Properties of Amides 268
10.2.4 酰胺的化学性质Chemical Properties of Amides 269
10.2.5 碳酸的酰胺Amides of Carbonic Acids 271
10.2.6 苯磺酰胺Benzenesulfonamide 273
10.3 硝基化合物Nitro Compounds 274
10.3.1 分类和命名Classification and Nomenclature 274
10.3.2 硝基化合物的结构Structures of Nitro Compounds 274
10.3.3 物理性质Physical Properties 274
10.3.4 化学性质Chemical Properties 275
习题 276
11 含硫、含磷有机化合物Sulfurated,Phosphorated Organic Compounds 280
11.1 含硫有机化合物Sulfurated Organic Compounds 280
11.1.1 含硫有机化合物的分类和命名Classification and Nomenclature of Sulfurated Organic Compounds 280
11.1.2 硫醇和硫酚Thiol and Thiophenol 282
11.1.3 硫醚Thioether 284
11.1.4 有机硫杀菌剂Organosulfur Compounds Fungicides 285
11.2 含磷有机化合物Phosphorated Organic Compounds 286
11.2.1 含磷有机化合物的分类和命名Classification and Nomenclature of Phosphorated Organic Compounds 286
11.2.2 膦酸和膦酸酯类化合物Phosphonic Acids and Phosphonate Esters 287
11.2.3 磷酸酯和硫代磷酸酯Phosphonate Esters and Thiophosphonate Esters 288
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 Base 292
12.1 杂环化合物Heterocyclic Compounds 292
12.1.1 杂环化合物的分类和命名Classification and Nomenclature of Heterocyclic Compounds 293
12.1.2 杂环化合物的结构与芳香性Structures and Aromaticity of Heterocyclic Compounds 294
12.1.3 杂环化合物的化学性质Chemical Properties of Heterocyclic Compounds 296
12.1.4 杂环化合物及其衍生物选述Selected Introduction of Heterocyclic Compounds and Their Derivatives 299
12.2 生物碱Natural Base 310
12.2.1 生物碱概述Introduction of Natural Bases 310
12.2.2 生物碱的一般性质General Properties of Natural Bases 310
12.2.3 生物碱的一般提取方法General Extraction Methods of Natural Bases 311
12.2.4 个别化合物Typical Natural Bases 311
科苑拾贝 鸦片与海洛因 314
习题 314
13 碳水化合物Carbohydrate 316
13.1 单糖Monosaccharide 316
13.1.1 单糖的分类Classification of Monosaccharides 316
13.1.2 单糖的构型Configuration of Monosaccharides 318
13.1.3 单糖的结构Structures of Monosaccharides 319
13.1.4 单糖的物理性质Physical Properties of Monosaccharides 324
13.1.5 单糖的化学性质Chemical Properties of Monosaccharides 325
13.1.6 重要的单糖和糖的衍生物Important Monosaccharides and Derivatives of Monosaccharides 333
13.2 二糖Disaccharide 335
13.2.1 还原性二糖Reducing Disaccharide 335
13.2.2 非还原性二糖Non-reducing Disaccharides 337
13.3 多糖Polysaccharide 338
13.3.1 均多糖Homopolysaccharide 339
13.3.2 杂多糖Heteropo1ysaccharide 346
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 Acid 354
14.1 氨基酸Amino Acid 354
14.1.1 氨基酸的分类和结构Classification and Structures of Amino Acids 354
14.1.2 氨基酸的物理性质Physical Properties of Amino Acids 357
14.1.3 氨基酸的化学性质Chemical Properties of Amino Acids 358
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Protein 364
14.2.1 蛋白质的组成和分类Composition and Classification of Proteins 364
14.2.2 蛋白质的结构Structures of Proteins 365
14.2.3 蛋白质的理化性质Physical and Chemical Properties of Proteins 368
科苑拾贝 天然药物中的毒蛋白和多肽 372
14.3 核酸Nucleic Acid 372
14.3.1 核酸的组成Composition of Nucleic Acids 373
14.3.2 核苷Nucleoside 373
14.3.3 核苷酸和脱氧核苷酸Nucleotides and Deoxynucleotides 375
14.3.4 核酸的结构Structures of Nucleic Acids 376
14.3.5 核酸的理化性质Physical and Chemical Properties of Nucleic Acids 379
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 Lipids 384
15.1 油脂Oil 384
15.1.1 油脂的组成与结构Composition and Structures of Oil 384
15.1.2 油脂的理化性质Physical and Chemical Properties of Oil 386
15.1.3 肥皂和表面活性剂Soap and Surfactant 390
科苑拾贝 家用洗涤剂（粉） 392
15.2 类脂Lipids 393
15.2.1 蜡Wax 393
15.2.2 磷脂Phospholipids 394
15.2.3 甾族化合物Steroid 397
习题 401
16 有机化合物的波谱知识Spectroscopy Knowledge of Organic Compounds 402
16.1 电磁波谱的一般概念General Concepts of Electromagnetic Spectrum 402
16.1.1 转动光谱Rotation Spectrum 403
16.1.2 振动光谱Vibration Spectrum 403
16.1.3 电子光谱Electronic Spectrum 404
16.2 紫外光谱Ultraviolet Spectrum 404
16.2.1 电子跃迁类型Types of Electronic Transition 404
16.2.2 紫外光谱图Ultraviolet Spectrogram 405
16.2.3 紫外光谱图与分子结构的关系Relationships of Ultraviolet Spectrograms and Molecular Structures 406
16.2.4 紫外光谱的应用Application of Ultraviolet Spectrum 407
16.3 红外光谱Infrared Spectrum 407
16.3.1 分子振动和红外光谱Molecular Vibration and Infrared Spectrum 407
16.3.2 有机物官能团的红外光谱The Infrared Spectra of the Organic Functional Group 409
16.4 核磁共振谱Nuclear Magnetic Resonance Spectrum 411
16.4.1 基本知识Basic Knowledge 412
16.4.2 化学位移Chemical Shift 413
16.4.3 自旋偶合与自旋裂分Spin Coupling and Spin Splitting 415
16.4.4 核磁共振谱的应用Application of Nuclear Magnetic Resonance Spectra 417
16.5 质谱Mass Spectrum 417
科苑拾贝 近红外光谱技术的应用 421
习题 421
17 网络导航Network Navigation 424
17.1 开航前的话Before Sailing 424
17.2 从网上查出所需化学数据Chemical Datum from WWW 424
17.3 化学网站Chemical Links 426
17.4 文献检索Literature Searching 429
17.5 有机化学网站Organic Chemical Web 430
17.6 检索科技论文Searching of Science and Technology Thesises 432
17.7 生命科学的最新进展Advanced Developments of Life Sciences 434
习题 435
附录 有机化合物英文命名简介 436
主要参考文献 452