第1章　有機化學的基礎知識 1
1.1 有機化合物的一般特點(characteristic of organic compound) 1
1.2 共價鍵的屬性(feature of covalent bond) 1
1.3 分子式、構造式、構型式和構象式(molecular formula, constitution,configuration and conformation) 3
1.4 氫鍵(hydrogen bond) 4
1.5 有機化合物的分類(classification of organic compound) 5
1.6 簡單有機化合物的命名(nomenclature of simple organic compound) 7
1.6.1 烷烴的命名(nomenclature of alkane) 7
1.6.2 單環(huán)烷烴的命名(nomenclature of mono cycloalkane) 9
1.6.3 橋環(huán)烴的命名(nomenclature of bridged alkane) 10
1.6.4 螺環(huán)烴的命名(nomenclature of spirocyclic alkane) 12
1.6.5 烯烴的命名(nomenclature of alkene) 13
1.6.6 炔烴的命名(nomenclature of alkyne) 14
1.6.7 二烯烴的命名(nomenclature of diene) 15
1.6.8 芳烴的命名(nomenclature of arene) 15
1.6.9 鹵代烴的命名(nomenclature of halohydrocarbon) 17
1.6.10 醇的命名(nomenclature of alcohol) 18
1.6.11 酚的命名(nomenclature of phenol) 18
1.6.12 醚的命名(nomenclature of ether) 19
1.6.13 簡單醛、酮的命名(nomenclature of simple aldehyde and ketone) 19
1.6.14 簡單羧酸及其衍生物的命名(nomenclature of simple carboxylic acid and derivatives) 20
1.6.15 硝基化合物的命名(nomenclature of nitro compound) 21
1.6.16 胺類化合物的命名(nomenclature of amines) 21
習題(Problems) 21
1.7 氧化數(shù)(oxidation number) 21
1.7.1 電負性(electronegativity) 21
1.7.2 氧化數(shù)值(oxidation value) 22
1.7.3 用氧化數(shù)法確定有機基團的大小(determination of sequence of organic group by oxidation number) 22
1.7.4 用氧化數(shù)法處理氧化還原滴定結果(handling redox titration data by oxidation number) 23
1.8 廣義酸堿理論(theory of generalized acids and bases) 24
1.9 有機化合物中碳的構型(configuration of carbon in organic compound) 27
1.10 共振論與分子軌道理論(resonance theory and molecular orbital theory) 31
1.11 有機化合物的波譜簡介(introduction to spectroscopy of organic compound) 34
1.11.1 紫外光譜(ultraviolet spectrum) 34
1.11.2 紅外光譜(infrared spectrum) 37
1.11.3 核磁共振波譜(nuclear magnetic resonance spectroscopy) 43
1.11.4 質(zhì)譜(mass spectrum) 51
習題(Problems) 54

第2章　碳-碳單鍵化合物 55
2.1 烷烴(alkane) 55
2.1.1 烷烴的物理性質(zhì)及波譜(physical properties and spectrum of alkane) 55
2.1.2 烷烴的同分異構(isomerism of alkane) 57
2.1.3 烷烴的構象(conformation of alkane) 59
2.1.4 烷烴的化學性質(zhì)(chemical properties of alkane) 61
2.1.5 烷烴的來源(source of alkane) 64
2.2 環(huán)烷烴(cycloalkane) 65
2.2.1 環(huán)烷烴的分類和命名(classification and nomenclature of cycloalkane) 65
2.2.2 環(huán)烷烴的構象(conformation of cycloalkane) 66
2.2.3 環(huán)烷烴的反應(reaction of cycloalkane) 71
2.2.4 小環(huán)烷烴的制備(preparation of small-cycloalkane) 72
2.2.5 奇妙的立方烷(wonderful cubane)* 72
習題(Problems) 73

第3章　碳-碳重鍵化合物 74
3.1 分類及結構(classification and structure) 74
3.2 同分異構現(xiàn)象(isomerism) 75
3.3 物理性質(zhì)及波譜(physical properties and spectrum) 77
3.4 化學性質(zhì)(chemical properties) 78
3.4.1 親電加成反應(electrophilic addition) 78
3.4.2 親電加成反應的機理(mechanism of electrophilic addition) 84
3.4.3 馬氏加成與反馬氏加成(Markovnikov and anti-Markovnikov addition) 88
3.4.4 加氫反應(hydrogenation reaction) 89
3.4.5 α-氫的反應(reaction of α-hydrogen) 90
3.4.6 氧化反應(oxidation reaction) 90
3.4.7 自由基加成及機理(mechanism of radical addition) 92
3.4.8 卡賓的加成反應(addition reaction of carbene) 92
3.4.9 親核加成反應(nucleophilic addition reaction) 92
3.4.10 炔氫的反應(reaction of acetylenic hydrogen) 93
3.4.11 二烯烴的1,2-加成和1,4-加成反應(1,2-and 1,4-addition of diene) 94
3.4.12 聚合反應(polymerization) 95
3.4.13 烯烴的復分解反應(metathesis of alkene) 97
3.5 誘導效應和共軛效應(inductive effect and conjugated effect) 97
3.5.1 誘導效應(inductive effect) 97
3.5.2 共軛效應與超共軛效應(conjugated effect and hyperconjugative effect) 98
3.6 電環(huán)化與環(huán)加成反應(electrocyclic reaction and cycloaddition reaction) 100
3.6.1 電環(huán)化反應(electrocyclic reaction) 100
3.6.2 環(huán)加成反應(cycloaddition reaction) 103
3.7 烯烴和炔烴的制備(preparation of alkene and alkyne) 108
3.7.1 烯烴的制備(preparation of alkene) 108
3.7.2 炔烴的制備(preparation of alkyne) 109
3.8 螺環(huán)烯烴與螺共軛效應(spirocycloalkenes and spiroconjugation effect)* 110
習題(Problems) 111

第4章　芳烴及芳香性 114
4.1 芳烴(arene) 114
4.1.1 芳烴的分類(classification of arene) 114
4.1.2 芳烴的物理性質(zhì)及波譜(physical properties and spectrum of arene) 115
4.1.3 苯的結構(structure of benzene) 115
4.1.4 苯環(huán)上的親電取代反應(electrophilic substitution of benzene ring) 118
4.1.5 苯環(huán)上的定位效應(directing effect on benzene ring) 124
4.1.6 苯環(huán)上的親核取代反應(nucleophilic substitution on benzene ring) 130
4.1.7 苯環(huán)上的加成反應(addition reaction on benzene ring) 132
4.1.8 苯環(huán)上側鏈的反應(reaction of branched chain on benzene ring) 133
4.1.9 芳烴的來源及制備(source and preparation of arene) 134
4.2 多環(huán)芳烴(polycyclic arene) 135
4.2.1 分類(classification) 135
4.2.2 聯(lián)苯(biphenyl) 136
4.2.3 萘(naphthalene) 136
4.2.4 蒽(anthracene) 141
4.2.5 菲(phenanthrene) 143
4.2.6 其他稠環(huán)芳烴(other fused ring aromatic hydrocarbons) 143
4.2.7 Haworth合成(Haworth synthesis) 143
4.2.8 多苯代脂烴(polyphenyl hydrocarbons) 145
4.2.9 富勒烯(fullerene) 146
4.2.10 稠環(huán)化合物的命名(nomenclature of fused ring aromatic hydrocarbons) 147
4.3 芳香性, 非芳香性, 反芳香性, 同芳香性及反同芳香性(aromaticity,nonaromaticity, antiaromaticity, homoaromaticity and antihomoaromaticity) 147
4.4 致癌芳烴(carcinogenic arene) 153
習題(Problems) 154

第5章　手性化合物與手性合成 157
5.1 簡介(introduction) 157
5.2 平面偏振光(plane polarized light) 158
5.3 旋光性、旋光物質(zhì)與比旋光度(optical rotation, optically active substance and specific rotation) 158
5.4 分子的對稱性(molecular symmetry) 159
5.5 構型表示與標記(determination configuration) 162
5.5.1 Fischer投影式(Fischer projection formula) 162
5.5.2 D-L構型標記法(method of D-L-configuration labeling) 164
5.5.3 R-S 構型標記法(method of R-S-configuration labeling) 164
5.6 含一個手性碳原子的光學異構體(optical isomer of one chiral carbon atom) 167
5.7 含兩個手性碳原子的光學異構體(optical isomer of two chiral carbon atoms) 168
5.7.1 含兩個不同手性碳原子的光學異構體(optical isomer of distinct two chiral carbon atoms) 168
5.7.2 含兩個相似手性碳原子的光學異構體(optical isomer of similar two chiral carbon atoms) 168
5.8 含多個手性碳原子的光學異構體(optical isomer of multiple chiral carbon atoms) 169
5.9 環(huán)狀手性化合物(chiral compound of cyclo-hydrocarbon) 169
5.10 不含手性碳原子的光學異構體(optical isomer of non-containing chiral carbon atom) 170
5.10.1 含手性軸的化合物(compounds of containing chiral axis) 170
5.10.2 含手性面的化合物(compounds of containing chiral plane) 172
5.10.3 螺旋化合物(screw compound) 173
5.11 外消旋體的合成與拆分(synthesis and resdution of racemate) 173
5.12 旋光方向與構型的關系(rotatory direction and configuration) 174
習題(Problems) 175

第6章　碳-鹵極性單鍵化合物 178
6.1 脂肪鹵代烴(aliphatic halohydrocarbons) 178
6.1.1 鹵代烴的分類(classification of halohydrocarbons) 178
6.1.2 鹵代烴的物理性質(zhì)及波譜(physical properties and spectrum of halohydrocarbons) 179
6.1.3 鹵代烴的親核取代反應(nucleophilic substitution of halohydrocarbons) 179
6.1.4 親核取代反應的機理(mechanism of nucleophilic substitution) 182
6.1.5 影響反應歷程的因素(influencing factor of reaction mechanism) 186
6.1.6 消除反應(elimination reaction) 193
6.1.7 與金屬的反應(reaction with metals) 197
6.2 芳香鹵代烴(halogenated aromatic hydrocarbons) 198
6.2.1 芳香鹵代烴的結構特征(structural feature of halogenated aromatic hydrocarbons) 198
6.2.2 鹵苯的反應(reaction of halobenzene) 199
6.3 鹵代烴的制備(preparation of halohydrocarbons) 200
6.4 重要的鹵代烴(important halohydrocarbons) 202
習題(Problems) 203

第7章　碳-氧（硫） 極性單鍵化合物 206
7.1 醇類(alcohols) 206
7.1.1 醇的結構、分類和異構(structure, classification and isomerism of alcohols) 206
7.1.2 醇的物理性質(zhì)及波譜(physical properties and spectrum of alcohols) 208
7.1.3 醇的化學性質(zhì)(chemical properties of alcohols) 210
7.1.4 醇的制備(preparation of alcohols) 214
7.1.5 多元醇(polyalcohols) 215
7.2 醚類(ethers) 219
7.2.1 醚的結構、分類、異構和命名(structure, classification, isomerism and nomenclature of ethers) 219
7.2.2 醚的物理性質(zhì)及波譜(physical properties and spectrum of ethers) 220
7.2.3 醚的化學性質(zhì)(chemical properties of ethers) 221
7.2.4 環(huán)氧乙烷(epoxyethane) 223
7.2.5 冠醚(crown ether) 225
7.3 酚類(phenols) 226
7.3.1 酚的結構(structure of phenols) 226
7.3.2 酚的物理性質(zhì)及波譜(physical properties and spectrum of phenols) 226
7.3.3 酚的化學性質(zhì)(chemical properties of phenols) 227
7.3.4 多元酚(polyphenols) 234
7.3.5 酚的制備(preparation of phenols) 235
習題(Problems) 236
7.4 硫醇和硫醚(thiol and thioether) 239
7.4.1 制備(preparation) 239
7.4.2 物理性質(zhì)(physical properties) 239
7.4.3 化學性質(zhì)(chemical properties) 239
7.5 芳磺酸(aromatic sulfonic acid) 240
7.5.1 芳磺酸的命名(nomenclature of aromatic sulfonic acid) 240
7.5.2 芳磺酸的制備(preparation of aromatic sulfonic acid) 241
7.5.3 芳磺酸的物理性質(zhì)(physical properties of aromatic sulfonic acid) 241
7.5.4 芳磺酸的化學性質(zhì)(chemical properties of aromatic sulfonic acid) 242
7.5.5 芳磺酰氯和芳磺酰胺(aromatic sulfonyl chloride and aromatic sulfamine) 243
7.5.6 烷基苯磺酸鈉和表面活性劑(alkyl benzene sulfonic acid sodium and surfactant) 245
7.5.7 離子交換樹脂(ion exchange resin) 245

第8章　碳-氧極性重鍵化合物——醛和酮 247
8.1 醛、酮的結構、分類及命名(structure, classification and nomenclature of aldehyde and ketone) 247
8.2 醛、酮的物理性質(zhì)及波譜(physical properties and spectrum of aldehyde and ketone) 248
8.3 醛、酮的親核加成反應(nucleophilic addition reaction of aldehyde and ketone) 250
8.3.1 與氫氰酸的加成(addition reaction with hydrocyanic acid) 251
8.3.2 與亞硫酸氫鈉的加成(addition reaction with sodium bisulfite) 252
8.3.3 與醇的加成(addition reaction with alcohol) 252
8.3.4 與水的加成(addition reaction with water) 254
8.3.5 與金屬有機化合物的加成(reaction with organometallic compound) 255
8.3.6 與氨及其衍生物的加成縮合反應(reaction with ammonia and its derivatives) 257
8.3.7 Wittig反應(Wittig reaction) 259
8.4 α-氫的反應(reaction of α-hydrogen) 259
8.4.1 鹵化反應(halogenating reaction) 260
8.4.2 羥醛縮合反應(aldol condensation) 261
8.4.3 Perkin反應(Perkin reaction) 265
8.4.4 Mannich反應(Mannich reaction) 265
8.5 氧化還原反應(redox reaction) 266
8.5.1 與Tollen試劑和Fehling試劑反應(reaction with Tollen and Fehling reagent) 266
8.5.2 還原成醇(reduction to alcohol) 267
8.5.3 Meerwein-Ponndorf還原(Meerwein-Ponndorf reduction) 268
8.5.4 Clemmensen還原(Clemmensen reduction) 268
8.5.5 Wolff-Kishner-黃鳴龍還原(Wolff-Kishner-Huang Minlon reduction) 268
8.5.6 Cannizzaro反應(Cannizzaro reaction) 269
8.5.7 安息香縮合(benzoin condensation) 269
8.5.8 二苯酮重排(benzophenone rearrangement) 270
8.5.9 Baeyer-Villiger重排(Baeyer-Villiger rearrangement) 271
8.5.10 Favorskii重排(Favorskii rearrangement) 271
8.6 α,β-不飽和醛、酮的性質(zhì)(properties of α,β-unsaturated aldehyde and ketone) 271
8.7 醛、酮的制備(preparation of aldehyde and ketone) 273
8.8 重要的醛、酮(important aldehyde, ketone) 276
習題(Problems) 280

第9章　碳-氧極性重鍵化合物——羧酸及其衍生物 282
9.1 羧酸(carboxylic acid) 282
9.1.1 羧酸的結構(structure of carboxylic acid) 282
9.1.2 羧酸的分類和命名(classification and nomenclature of carboxylic acid) 283
9.1.3 羧酸的物理性質(zhì)及波譜(physical properties and spectrum of carboxylic acid) 284
9.1.4 羧酸的化學性質(zhì)(chemical properties of carboxylic acid) 286
9.1.5 二元羧酸的熱分解反應(thermal decomposition reaction of dicarboxylic acid) 292
9.1.6 羥基酸 (hydroxyl acid) 293
9.1.7 羧酸的制備(preparation of carboxylic acid) 294
習題(Problems) 297
9.2 羧酸衍生物(carboxylic acid derivatives) 298
9.2.1 分類和命名(classification and nomenclature) 298
9.2.2 物理性質(zhì)及波譜(physical properties and spectrum) 299
9.2.3 水解、醇解、氨解反應 (hydrolysis, alcoholysis and aminolysis) 300
9.2.4 與金屬有機化合物的反應(reaction with organometallic compound) 304
9.2.5 還原反應(reduction reaction) 305
9.2.6 酯縮合反應(ester condensation) 306
9.2.7 Hofmann重排(Hofmann rearrangement) 307
9.2.8 有關NBS的一些反應 (reactions about NBS) 307
9.2.9 有關丙二酸二乙酯和乙酰乙酸乙酯的反應 (reactions about diethyl malonate and ethyl acetoacetate) 308
9.2.10 Knoevenagel反應 (Knoevenagel reaction) 311
9.2.11 Michael加成 (Michael addition) 312
9.2.12 Weiss反應(Weiss reaction) 313
習題(Problems) 314

第10章　碳-氮極性單鍵化合物 318
10.1 硝基化合物(nitro compound) 318
10.1.1 硝基化合物的分類及命名(classification and nomenclature of nitro compound) 318
10.1.2 硝基化合物的物理性質(zhì)及波譜 (physical properties and spectrum of nitro compound) 319
10.1.3 硝基化合物的化學性質(zhì)(chemical properties of nitro compound) 320
10.2 胺類(amines) 326
10.2.1 胺類的結構、分類、異構和命名(structure, classification, isomerism and nomenclature of amines) 326
10.2.2 胺類的物理性質(zhì)和波譜 (physical properties and spectrum of amines) 330
10.2.3 胺類的化學性質(zhì)(chemical properties of amines) 331
10.2.4 季銨鹽和季銨堿 (quaternary ammonium salt and quaternary ammonium hydroxide) 338
10.2.5 多元胺(polyamines) 340
10.2.6 胺的制備(preparation of amines) 340
10.2.7 重氮和偶氮化合物(diazonium salt and azo compound) 341
10.3 禁用染料(prohibited dyes) 346
習題(Problems) 347

第11章　雜環(huán)化合物 349
11.1 分類和命名(classification and nomenclature) 349
11.2 呋喃、噻吩、吡咯 (furan, thiophene and pyrrole) 351
11.2.1 呋喃、噻吩、吡咯的結構 (structure of furan, thiophene and pyrrole) 351
11.2.2 呋喃、噻吩、吡咯的物理性質(zhì)(physical properties of furan, thiophene and pyrrole) 352
11.2.3 呋喃、噻吩、吡咯的化學性質(zhì)(chemical properties of furan, thiophene and pyrrole) 353
11.2.4 呋喃、噻吩、吡咯的制備(preparation of furan, thiophene and pyrrole) 354
11.3 吡啶(pyridine) 355
11.3.1 吡啶的結構(structure of pyridine) 355
11.3.2 吡啶的物理性質(zhì) (physical properties of pyridine) 355
11.3.3 吡啶的化學性質(zhì)(chemical properties of pyridine) 355
11.3.4 吡啶的制備(preparation of pyridine) 357
11.4 其他雜環(huán)化合物 (other heterocyclic compound) 357
習題(Problems) 360

第12章　天然有機化合物 362
12.1 糖類(carbohydrates) 362
12.1.1 糖類的分類(classification of carbohydrates) 362
12.1.2 單糖(monosaccharides) 363
12.1.3 二糖(disaccharides) 371
12.1.4 多糖(polysaccharides) 373
12.1.5 異頭效應與糖類的構象(anomeric effect and conformation of carbohydrates) 375
習題(Problems) 376
12.2 氨基酸(amino acid) 377
12.2.1 氨基酸的分類和命名(classification and nomenclature of amino acid) 377
12.2.2 氨基酸的結構(stucture of amino acid) 379
12.2.3 氨基酸的化學性質(zhì)(chemical properties of amino acid) 380
12.2.4 氨基酸的制備(preparation of amino acid) 382
12.3 蛋白質(zhì)(protein) 383
12.3.1 蛋白質(zhì)的分類和結構(classification and structure of protein) 383
12.3.2 蛋白質(zhì)的理化性質(zhì)(physical and chemical properties of protein) 386
12.4 類脂和生物堿(lipids and alkaloids) 388
12.4.1 油脂(natural oils) 388
12.4.2 蠟(waxes) 390
12.4.3 萜類(terpenes) 390
12.4.4 甾族化合物(steroids) 392
12.4.5 生物堿(alkaloids) 393

參考文獻 396