《有机化学（英文版）》（第二版）共21章，分别为概论，烷烃，烯烃，共轭二烯烃，环烷烃，炔烃，立体化学，卤代烃，苯及芳香化学，醇、酚、醚，核磁共振波谱，红外光谱，醛和酮，羧酸及其衍生物，双官能团化合物，胺及其他含氮化合物，杂环化合物，碳水化合物，氨基酸、多肽、蛋白质和核酸，金属有机化合物，周环反应等内容。本书注重对各类化合物结构的介绍，以强化结构决定性质和反应这一有机化合物的基本特征。本书在编写时引入有机化学家事迹、化学史、学科前沿等内容，以增加学生的学习兴趣，提高科学素养。本书为英文写作，有助于提升学习者专业英语的阅读和理解能力，提升与国外高校和科研机构的合作与交流能力。本书采取双色印刷，对重点专业名词和官能团转化进行颜色区分，有利于掌握有机化学的基本规律。
《有机化学（英文版）》（第二版）可作为化学类、化工与制药类、材料类、药学类、食品科学与工程类、生物工程类、环境科学与工程类、轻化工程类等专业本科生及研究生的教材，也可作为有关研究院所和企业科研人员的参考书。

Chapter1 Introduction\t001
1.1 The Development of Organic Chemistry\t001
1.2 The Structural Theory of Organic Chemistry\t001
1.2.1 Atomic orbitals\t002
1.2.2 Ionic bonding\t002
1.2.3 Covalent bonding \t003
1.2.4 Hybridization\t003
1.2.5 Polar covalent bond, electronegativity and dipole moment\t007
1.3 Acid-Base Theory in Organic Chemistry\t008
1.3.1 Brnsted-Lowry acids and bases\t008
1.3.2 Lewis acids and bases\t009
1.4 Function Groups and Classify of Organic
Chemical Compounds\t010
Extending reading: Linus Pauling\t012
Problems\t016
Chapter2 Alkanes\t017
2.1 Introduction\t017
2.2 Nomenclature of Alkanes\t018
2.2.1 Nomenclature of unbranched alkyl groups\t020
2.2.2 Nomenclature of branched-chain alkanes\t020
2.2.3 Nomenclature of branched alkyl groups\t022
2.2.4 Classification of hydrogen atoms\t023
2.3 Structure and Conformations of Alkanes\t023
2.3.1 Structure of methane\t023
2.3.2 Structure of ethane\t024
2.3.3 Free rotation, conformations, torsional strain of the carbon-carbon single bond\t025
2.3.4 Propane and the butane\t027
2.3.5 Conformations of n-butane: van der Waals repulsion\t028
2.4 Physical Properties of Alkanes\t029
2.4.1 Boiling point\t029
2.4.2 Melting point\t030
2.4.3 Solubility in water\t031
2.5 Chemical Properties of Alkanes\t032
2.5.1 Combustion of alkanes\t032
2.5.2 Pyrolysis of alkanes: Cracking\t034
2.5.3 Halogenation of alkanes\t035
2.6 Occurrence and Uses of Alkanes\t044
2.6.1 Sources of alkanes: petroleum\t044
2.6.2 Petroleum refining\t045
2.6.3 Cracking\t045
Extending reading: Jacobus Henricus van’t Hoff\t045
Problems\t047
Chapter3 Alkenes\t049
3.1 Structure of Alkenes \t049
3.2 Nomenclature and Geometric Isomerism of Alkenes\t050
3.2.1 Nomenclature of alkenes\t050
3.2.2 Geometric isomerism of alkenes and its nomenclature\t051
3.3 Physical Properties of Alkenes\t052
3.4 Preparation and Uses of Alkenes\t053
3.4.1 Dehydration\t053
3.4.2 Dehydrohalogenation\t054
3.4.3 Cracking\t055
3.4.4 Use of alkenes\t055
3.5 Chemical Properties of Alkenes\t055
3.5.1 Catalytic hydrogenation reaction\t055
3.5.2 Electrophilic addition to alkenes\t056
3.5.3 HBr free radical addition\t060
3.5.4 Addition of diboranes\t061
3.5.5 Reactions of alkenes with oxygen electrophiles\t062
3.5.6 The reaction of α-H\t066
3.6 Polymer and Plastics\t067
Extending reading: Synthesis of Palytoxin\t069
Problems\t070
Chapter4 Dienes and Conjugation\t072
4.1 Nomenclature of Dienes\t072
4.2 Structure and Stability of Conjugated Dienes\t073
4.2.1 Conjugative effect\t073
4.2.2 Molecular orbital (MO) of 1,3-butadiene\t074
4.3 Chemical Properties of Conjugative Dienes\t075
4.3.1 Electrophile addition\t075
4.3.2 Diels-Alder reaction\t076
4.4 Rubber\t078
Extending reading 1: Otto Paul Hermann Diels\t080
Extending reading 2: Kurt Alder\t080
Problems\t081
Chapter5 Cycloalkanes\t083
5.1 Nomenclature of Cycloalkanes\t083
5.1.1 Nomenclature of monocycloalkanes\t083
5.1.2 Nomenclature of polycycloalkanes\t084
5.2 Stabilities of Cycloalkanes\t086
5.3 Structures and Conformation of Cycloalkanes\t087
5.3.1 Structures and conformation of cyclopropane and cyclobutane\t087
5.3.2 Structures and conformation of cyclopentane\t089
5.3.3 Structures and conformation of cyclohexane\t089
5.3.4 Conformations of higher cycloalkanes\t091
5.3.5 Substituted cyclohexanes: axial and equatorial hydrogen atoms\t092
5.4 Chemical Properties of Cycloalkanes\t096
Extending reading: Derek Harold Richard Barton\t097
Problems\t098
Chapter6 Alkynes\t101
6.1 Structure of Alkynes\t101
6.2 Nomenclature of Alkynes\t102
6.3 Physical Properties of Alkynes\t103
6.4 Preparation and Uses of Alkynes\t103
6.4.1 Preparation of ethyne (HC≡CH)\t103
6.4.2 By elimination reaction\t103
6.5 Chemical Properties of Alkynes\t104
6.5.1 Acidity of terminal alkynes\t104
6.5.2 Addition by electrophilic reagents\t106
6.5.3 Hydroboration/oxidation of alkynes\t108
6.5.4 Reduction of alkynes\t108
6.5.5 Oxidation of alkynes\t109
6.5.6 Alkynes anions as nucleophiles\t110
Extending reading: Discovery of Acetylene\t110
Problems\t111
Chapter7 Stereochemistry\t113
7.1 Enantiomerism and Chirality\t113
7.2 Plane Polarized Light, Optical Activity and Specific Rotation\t116
7.3 Fischer Projection\t117
7.4 Configuration Representation Method, Configuration Labeling and Isomer Naming\t118
7.4.1 R/S absolute configuration representation\t119
7.4.2 D/L Relative configuration representation\t119
7.5 Diastereomers\t120
7.6 Resolution of Racemates\t121
Extending reading: The Critical Role of Stereochemistry in Organic Chemistry — Insights from the Thalidomide Tragedy\t122
Problems\t123
Chapter8 Alkyl Halides\t125
8.1 Classification and Nomenclature of Halogenated Hydrocarbons\t125
8.2 Structure of Halides\t126
8.3 Physical Properties of Halides\t126
8.4 Chemical Properties of Halogenated Hydrocarbons\t127
8.4.1 Nucleophilic substitution reaction\t127
8.4.2 Elimination reactions of alkyl halides\t132
8.4.3 Organometallic compounds and their reactions\t133
8.5 Reaction Mechanism and Influencing Factors of Nucleophilic Substitution Reaction\t135
8.5.1 The mechanism for SN2 reaction\t135
8.5.2 The mechanism for SN1 reaction\t137
8.5.3 Factors affecting the rates of SN1 and SN2 reactions\t140
8.6 Mechanisms of Dehydrohalogenation\t147
8.6.1 Bimolecular elimination reaction: E2 reaction\t147
8.6.2 Unimolecular elimination reaction: E1 reaction\t148
8.7 Substitution versus Elimination\t149
8.7.1 SN2 versus E2 \t150
8.7.2 Tertiary halides: SN1 versus E1\t151
8.8 Halogenated Alkenes\t152
8.8.1 Vinyl halogenated alkenes\t152
8.8.2 Allyl halide alkenes\t153
8.9 Commonly Halogenated Hydrocarbons \t154
Extending reading: Paul Walden\t155
Problems\t156
Chapter9 Benzene and Aromatic Chemistry\t158
9.1 Structure of Benzene and Aromaticity\t159
9.1.1 Kekulé and the structure of benzene\t159
9.1.2 A resonance of bonding in benzene\t159
9.1.3 The stability of benzene\t161
9.1.4 The molecular orbitals of benzene\t162
9.2 Nomenclature of Benzene Derivatives\t163
9.3 Physical Properties of Benzene Derivatives\t164
9.4 Chemical Properties of Benzene Derivatives\t165
9.4.1 Reduction\t165
9.4.2 Oxidation of alkyl side-chains\t165
9.4.3 Free-radical halogenation of alkylbenzenes\t166
9.5 Electrophilic Aromatic Substitution Reactions of Substituted Benzenes\t167
9.5.1 Ortho, para-directing groups\t173
9.5.2 Meta-directing groups\t178
9.6 Polycyclic Aromatic Compounds\t181
9.6.1 Non-fused polycyclic aromatic hydrocarbons\t181
9.6.2 Fused polycyclic aromatic hydrocarbons\t181
9.7 Non-Benzene Aromatic Hydrocarbons\t185
9.7.1 Hückel rule\t185
9.7.2 Cyclobutadiene and cyclooctatetraene \t187
9.7.3 Annulene\t187
9.7.4 Cyclopentadiene and cycloheptatriene\t188
Extending reading: Discovery of Benzene and the Theory of Molecular Structure of Benzene\t188
Problems\t189
Chapter10 Alcohols, Phenols and Ethers\t192
10.1 Structure of Alcohols, Phenols and Ethers\t192
10.1.1 Structure of alcohols\t192
10.1.2 Structure of phenols\t192
10.1.3 Structure of ethers\t193
10.2 Nomenclature of Alcohols, Phenols and Ethers\t193
10.2.1 Nomenclature of alcohols\t193
10.2.2 Nomenclature of phenols\t194
10.2.3 Nomenclature of ethers\t195
10.3 Physical Properties of Alcohols, Phenols and Ethers\t195
10.3.1 Physical properties of alcohols\t195
10.3.2 Physical properties of phenols\t196
10.3.3 Physical properties of ethers\t197
10.4 Preparation and Uses of Alcohols\t197
10.4.1 Synthesis of alcohols by hydration of alkenes\t197
10.4.2 Synthesis of alcohols by addition to carbonyl groups\t199
10.4.3 Synthesis of alcohols by reduction of carbonyl-containing compounds\t200
10.5 Chemical Properties of Alcohols\t201
10.5.1 Acidity of alcohols\t201
10.5.2 Conversion to alkyl halides\t202
10.5.3 Dehydration of alcohols\t203
10.5.4 Esterification of alcohols\t204
10.5.5 Oxidation of alcohols\t206
10.6 Preparation and Uses of Phenols\t207
10.6.1 Laboratory synthesis\t207
10.6.2 Industrial synthesis\t207
10.7 Chemical Properties of Phenols\t208
10.7.1 Acidity of phenols\t208
10.7.2 Other reaction of the OH group of phenols\t209
10.7.3 Reaction of the benzene ring of phenols\t211
10.8 Preparation of Ethers\t213
10.9 Chemical Properties of Ethers\t214
10.9.1 The formation of oxonium salts\t214
10.9.2 Acid-catalyzed cleavage of ethers\t214
10.9.3 Autoxidation of ethers\t215
10.10 Thiols, Sulfides and Disulfides\t215
Extending reading: Victor Grignard\t217
Problems\t218
Chapter11 Nuclear Magnetic Resonance Spectroscopy\t219
11.1 Principles of Nuclear Magnetic Resonance\t219
11.1.1 Discovery of nuclear magnetic resonance\t219
11.1.2 Spin phenomenon of atomic nucleus\t219
11.1.3 The reasons of nuclear magnetic resonance\t219
11.2 Chemical Shift\t221
11.2.1 Definition of chemical shift\t221
11.2.2 Shielding effect\t221
11.2.3 Practical representation of chemical shift\t222
11.2.4 Factors affecting chemical shift\t223
11.3 Chemical Shifts of Characteristic Protons in 1H-NMR\t225
11.4 Integration Curves and Peak Areas\t228
11.5 Spin Coupling\t228
11.5.1 The causes of spin coupling\t228
11.5.2 Coupling constant (J)\t230
11.5.3 The law of coupling and splitting\t230
11.5.4 Spectrum analysis\t231
11.6 NMR Instrument\t233
11.7 Carbon Spectrum (13C-NMR)\t234
Extended reading: Paul Lauterbur\t235
Problems\t237
Chapter12 Infrared Spectroscopy\t241
12.1 Theoretical Background\t241
12.1.1 Introduction\t241
12.1.2 Generation conditions of infrared absorption spectra\t242
12.1.3 Molecular vibration\t243
12.1.4 Vibrational forms of molecules\t244
12.2 The Infrared Spectrometer\t245
12.3 Characteristic Absorption of Functional Groups\t247
12.3.1 The functional group and fingerprint regions\t247
12.3.2 Characteristic infrared absorption bands\t248
12.3.3 The intensity of absorption bands\t249
12.3.4 The infrared spectra of alkane, haloalkane, alkene, benzene and alcohol\t249
12.4 Identifying Infrared Spectra\t251
Extended reading: Kirchhoff and Bunsen on Spectroscopy\t253
Problems\t254
Chapter13 Aldehydes and Ketones\t259
13.1 Structure and Nomenclature of Aldehydes and Ketones\t259
13.1.1 Structure and bonding of carbonyl group\t259
13.1.2 Nomenclature of aldehydes and ketones\t260
13.1.3 Physical properties\t261
13.2 Preparation of Aldehydes and Ketones\t261
13.2.1 Oxidation of alcohols (dehydrogenation)\t261
13.2.2 Oxidation of alkenes (ozonolysis)\t263
13.2.3 Hydrolysis of gem-dihalides\t263
13.2.4 Hydration of alkynes\t263
13.2.5 Friedel-Crafts acylation\t263
13.2.6 Hydroformylation of the linear α-olefins\t264
13.2.7 Oxidation of side chain of arenes\t264
13.3 Reactions of Aldehydes and Ketones\t265
13.3.1 Nucleophilic addition \t265
13.3.2 The activity of α-hydrogen in aldehydes and ketones \t270
13.3.3 Oxidation reactions\t275
13.3.4 Reduction\t276
13.4 α,β-Unsaturated Carbonyl Compounds\t277
Extended reading: Organic Chemist Huang Minglong\t278
Problems\t279
Chapter14 Carboxylic Acids and Acid Derivatives\t281
14.1 Nomenclature of Carboxylic Acids and Their Derivatives\t281
14.1.1 Nomencalture of carboxylic acids\t281
14.1.2 Nomenclature of carboxylic acid derivatives\t284
14.2 Structure and Physical Properties of Carboxylic Acids and Their Derivatives\t287
14.2.1 Structure of carboxylic acids and their derivatives\t287
14.2.2 Physical properties of carboxylic acids and their derivatives\t290
14.3 Preparation of Carboxylic Acids\t291
14.3.1 Oxidation reaction\t291
14.3.2 Hydrolysis of carboxylic acid derivatives \t293
14.3.3 Reaction of organometallic compounds with carbon dioxide\t293
14.3.4 Other methods\t294
14.4 Acidity of Carboxylic Acids \t295
14.5 Formation of Acid Halides and Anhydrides\t298
14.5.1 Formation of acid halides \t298
14.5.2 Formation of acid anhydrides\t299
14.6 Hydrolysis of Carboxylic Acid Derivatives\t301
14.6.1 Hydrolysis reaction\t301
14.6.2 Hydrolysis reaction mechanism \t302
14.7 Alcoholysis of Carboxylic Acid Derivatives \t304
14.7.1 Acylation\t304
14.7.2 Transesterification\t306
14.7.3 Esterification reaction mechanism \t306
14.8 Aminolysis of Carboxylic Acid Derivatives\t308
14.8.1 Reaction of carboxylic acid derivatives with amines\t308
14.8.2 Nucleophilic substitution reaction mechanism of amines\t310
14.9 Reaction of Carboxylic Acid Derivatives with Metal Reagents\t310
14.9.1 Reaction with metal magnesium reagents\t310
14.9.2 Reaction with metal lithium reagents\t311
14.9.3 Reaction with metal copper-lithium reagents\t311
14.9.4 Reaction with metal cadmium reagents\t312
14.10 Reductions of Carboxylic Acids and Their Derivatives\t312
14.10.1 Reduction of carboxylic acids\t312
14.10.2 Reduction of acid halides\t313
14.10.3 Reduction of esters\t314
14.10.4 Reduction of amides\t314
14.10.5 Reduction of nitriles\t315
14.11 Other Reactions of Carboxylic Acids and Their Derivatives\t316
14.11.1 Decarboxylation reaction\t316
14.11.2 α-Substituted carboxylic acids and their derivatives\t318
14.11.3 Elimination reaction of esters\t319
14.11.4 Hoffmann degradation reaction of amides\t320
14.12 Lactones\t320
14.13 Lipids and Waxes \t322
14.14 Carbonic Acid Derivatives \t323
14.15 Surfactants and Soaps \t324
Extended reading 1: August Wilhelm von Hofmann\t326
Extended reading 2: Aspirin (acetylsalicylic acid)\t327
Problems\t327
Chapter15 Difunctional Compounds\t333
15.1 Introduction\t333
15.2 Hydroxy Aldehydes and Ketones\t334
15.2.1 Properties\t334
15.2.2 Preparation\t334
15.2.3 Reactions\t335
15.3 Hydroxy Acids\t335
15.3.1 Properties\t335
15.3.2 Preparation\t335
15.3.3 Dehydration of hydroxy acid\t336
15.4 Dicarboxylic Acids\t337
15.4.1 Property and reactions\t337
15.4.2 Acidity of dicarboxylic acids\t338
15.5 Dicarbonyl Compounds\t338
15.5.1 Acidity of β-dicarbonyl compounds and stability of enol anion\t338
15.5.2 Diethyl malonate\t339
15.5.3 Ethyl acetoacetate\t340
15.5.4 Michael addition reaction\t341
15.6 Summary\t342
Extended reading: Possible Substitutes for White Pollution—Lactic Acid Polymer\t344
Problems\t344
Chapter16 Amines and Other Nitrogen-Containing Compounds\t348
16.1 Amines\t348
16.1.1 Nomenclature\t348
16.1.2 Structure and physical properties\t350
16.1.3 Preparation\t351
16.1.4 Chemical properties\t354
16.1.5 Reactions of diazonium ions\t361
16.2 Nitro Compounds\t363
16.3 Nitriles\t365
16.3.1 Nomenclature\t365
16.3.2 Physical properties\t365
16.3.3 Preparation\t365
16.3.4 Reactions of nitriles\t365
Extended reading: The Development of Nitroglycerin\t366
Problems\t368
Chapter17 Heterocyclic Compounds\t370
17.1 Heterocyclic System\t370
17.2 Classification and Nomenclature of Heterocycles \t371
17.3 Structure and Aromaticity of Heterocycles\t372
17.4 Five-Membered Unsaturated Heterocycles\t373
17.4.1 Furan\t373
17.4.2 Thiophene\t375
17.4.3 Pyrrole\t375
17.4.4 Indole\t376
17.5 Six-Membered Unsaturated Heterocycles\t378
17.6 Quinoline and Isoquinoline\t380
17.6.1 Quinoline\t380
17.6.2 Isoquinoline\t381
Extended reading: Tu Youyou and Artemisinin\t382
Problems\t383
Chapter18 Carbohydrates and Nucleic Acids\t386
18.1 Stereochemistry of Sugars\t386
18.1.1 The D and L notation\t386
18.1.2 Configurations of aldoses\t387
18.1.3 Configurations of ketoses\t389
18.2 Structure of Glucose\t389
18.3 Reactions of Monosaccharides \t392
18.3.1 Reduction\t392
18.3.2 Oxidation\t393
18.3.3 Osazone formation\t394
18.3.4 Ester formation\t395
18.3.5 Chain elongation\t395
18.3.6 Chain shortening\t396
18.4 Disaccharides\t396
18.5 Polysaccharides\t399
Extended reading: Hermann Emil Fischer\t401
Problems\t403
Chapter19 Amino Acids, Peptides, Proteins and Nucleic Acids\t405
19.1 Amino Acids\t405
19.1.1 Nomenclature of amino acids\t405
19.1.2 Physical properties of amino acids\t407
19.1.3 The acidity and alkalinity of amino acids\t407
19.1.4 Amino acid reaction\t410
19.1.5 Amino acid synthesis\t412
19.2 Peptides and Proteins\t413
19.2.1 Peptide nomenclature\t414
19.2.2 Synthesis of peptides and proteins\t414
19.2.3 Determination of polypeptide structure\t419
19.2.4 Protein hierarchy\t424
19.3 Enzyme\t427
19.4 Nucleic Acid\t428
Extended reading: Human Genome Project\t431
Problems\t432
Chapter20 Organometallic Compounds\t434
20.1 Preparation of Organometallic Compounds\t434
20.1.1 Preparation of organolithium compounds\t434
20.1.2 Preparation of organomagnesium compounds\t435
20.1.3 Preparation of organocopper compounds\t435
20.1.4 Preparation of organozinc compounds\t436
20.2 Main Reactions of Organometallic Compounds\t436
20.2.1 Organometallic compounds as Brnsted bases\t436
20.2.2 Organometallic compounds as nucleophilic reagents\t437
Extended reading: Karl Ziegler\t440
Problems\t440
Chapter21 Orbitals and Organic Chemistry: Pericyclic Reactions\t443
21.1 Introduction\t443
21.1.1 Evolution of the theory of concerted reactions\t443
21.1.2 A review of π molecular orbitals\t444
21.1.3 Interactions between molecular orbitals\t445
21.2 Electrocyclic Reaction\t445
21.3 Cycloaddition Reaction\t447
21.3.1 Photochemical dimerization of alkenes\t447
21.3.2 Diels-Alder reaction\t448
21.4 Sigmatropic Rearrangements\t448
Extended reading: Robert Burns Woodward\t449
Problems\t450
Reference\t452