有機(jī)化學(xué)

第1章　有機(jī)化學(xué)的基礎(chǔ)知識 1
1.1 有機(jī)化合物的一般特點(diǎn)(characteristic of organic compound) 1
1.2 共價鍵的屬性(feature of covalent bond) 1
1.3 分子式、構(gòu)造式、構(gòu)型式和構(gòu)象式(molecular formula, constitution,configuration and conformation) 3
1.4 氫鍵(hydrogen bond) 4
1.5 有機(jī)化合物的分類(classification of organic compound) 5
1.6 簡單有機(jī)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(xí)題(Problems) 21
1.7 氧化數(shù)(oxidation number) 21
1.7.1 電負(fù)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(jī)基團(tuán)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(jié)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(jī)化合物中碳的構(gòu)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(jī)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(xí)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(gòu)(isomerism of alkane) 57
2.1.3 烷烴的構(gòu)象(conformation of alkane) 59
2.1.4 烷烴的化學(xué)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(gòu)象(conformation of cycloalkane) 66
2.2.3 環(huán)烷烴的反應(yīng)(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(xí)題(Problems) 73

第3章　碳-碳重鍵化合物 74
3.1 分類及結(jié)構(gòu)(classification and structure) 74
3.2 同分異構(gòu)現(xiàn)象(isomerism) 75
3.3 物理性質(zhì)及波譜(physical properties and spectrum) 77
3.4 化學(xué)性質(zhì)(chemical properties) 78
3.4.1 親電加成反應(yīng)(electrophilic addition) 78
3.4.2 親電加成反應(yīng)的機(jī)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(yīng)(hydrogenation reaction) 89
3.4.5 α-氫的反應(yīng)(reaction of α-hydrogen) 90
3.4.6 氧化反應(yīng)(oxidation reaction) 90
3.4.7 自由基加成及機(jī)理(mechanism of radical addition) 92
3.4.8 卡賓的加成反應(yīng)(addition reaction of carbene) 92
3.4.9 親核加成反應(yīng)(nucleophilic addition reaction) 92
3.4.10 炔氫的反應(yīng)(reaction of acetylenic hydrogen) 93
3.4.11 二烯烴的1,2-加成和1,4-加成反應(yīng)(1,2-and 1,4-addition of diene) 94
3.4.12 聚合反應(yīng)(polymerization) 95
3.4.13 烯烴的復(fù)分解反應(yīng)(metathesis of alkene) 97
3.5 誘導(dǎo)效應(yīng)和共軛效應(yīng)(inductive effect and conjugated effect) 97
3.5.1 誘導(dǎo)效應(yīng)(inductive effect) 97
3.5.2 共軛效應(yīng)與超共軛效應(yīng)(conjugated effect and hyperconjugative effect) 98
3.6 電環(huán)化與環(huán)加成反應(yīng)(electrocyclic reaction and cycloaddition reaction) 100
3.6.1 電環(huán)化反應(yīng)(electrocyclic reaction) 100
3.6.2 環(huán)加成反應(yīng)(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(yīng)(spirocycloalkenes and spiroconjugation effect)* 110
習(xí)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(jié)構(gòu)(structure of benzene) 115
4.1.4 苯環(huán)上的親電取代反應(yīng)(electrophilic substitution of benzene ring) 118
4.1.5 苯環(huán)上的定位效應(yīng)(directing effect on benzene ring) 124
4.1.6 苯環(huán)上的親核取代反應(yīng)(nucleophilic substitution on benzene ring) 130
4.1.7 苯環(huán)上的加成反應(yīng)(addition reaction on benzene ring) 132
4.1.8 苯環(huán)上側(cè)鏈的反應(yīng)(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(xí)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(gòu)型表示與標(biāo)記(determination configuration) 162
5.5.1 Fischer投影式(Fischer projection formula) 162
5.5.2 D-L構(gòu)型標(biāo)記法(method of D-L-configuration labeling) 164
5.5.3 R-S 構(gòu)型標(biāo)記法(method of R-S-configuration labeling) 164
5.6 含一個手性碳原子的光學(xué)異構(gòu)體(optical isomer of one chiral carbon atom) 167
5.7 含兩個手性碳原子的光學(xué)異構(gòu)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(xué)異構(gòu)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(xué)異構(gòu)體(optical isomer of similar two chiral carbon atoms) 168
5.8 含多個手性碳原子的光學(xué)異構(gòu)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(xué)異構(gòu)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(gòu)型的關(guān)系(rotatory direction and configuration) 174
習(xí)題(Problems) 175