內容大鋼
《有機化學（英文版）》（第二版）共21章，分別為概論，烷烴，烯烴，共軛二烯烴，環烷烴，炔烴，立體化學，鹵代烴，苯及芳香化學，醇、酚、醚，核磁共振波譜，紅外光譜，醛和酮，羧酸及其衍生物，雙官能團化合物，胺及其他含氮化合物，雜環化合物，碳水化合物，氨基酸、多?、蛋白質和核酸，金屬有機化合物，周環反應等內容。本書注重對各類化合物結構的介紹，以強化結構決定性質和反應這一有機化合物的基本特徵。本書在編寫時引入有機化學家事跡、化學史、學科前沿等內容，以增加學生的學習興趣，提高科學素養。本書為英文寫作，有助於提升學習者專業英語的閱讀和理解能力，提升與國外高校和科研機構的合作與交流能力。本書採取雙色印刷，對重點專業名詞和官能團轉化進行顏色區分，有利於掌握有機化學的基本規律。
《有機化學（英文版）》（第二版）可作為化學類、化工與製藥類、材料類、藥學類、食品科學與工程類、生物工程類、環境科學與工程類、輕化工程類等專業本科生及研究生的教材，也可作為有關研究院所和企業科研人員的參考書。
目錄
Chapter 1 Introduction
1.1 The Development of Organic Chemistry
1.2 The Structural Theory of Organic Chemistry
1.2.1 Atomic orbitals
1.2.2 Ionic bonding
1.2.3 Covalent bonding
1.2.4 Hybridization
1.2.5 Polar covalent bond, electronegativity and dipole moment
1.3 Acid-Base Theory in Organic Chemistry
1.3.1 Brnsted-Lowry acids and bases
1.3.2 Lewis acids and bases
1.4 Function Groups and Classify of Organic Chemical Compounds
Extending reading: Linus Pauling
Problems
Chapter 2 Alkanes
2.1 Introduction
2.2 Nomenclature of Alkanes
2.2.1 Nomenclature of unbranched alkyl groups
2.2.2 Nomenclature of branched-chain alkanes
2.2.3 Nomenclature of branched alkyl groups
2.2.4 Classification of hydrogen atoms
2.3 Structure and Conformations of Alkanes
2.3.1 Structure of methane
2.3.2 Structure of ethane
2.3.3 Free rotation, conformations, torsional strain of the carbon-carbon single bond
2.3.4 Propane and the butane
2.3.5 Conformations of n-butane: van der Waals repulsion
2.4 Physical Properties of Alkanes
2.4.1 Boiling point
2.4.2 Melting point
2.4.3 Solubility in water
2.5 Chemical Properties of Alkanes
2.5.1 Combustion of alkanes
2.5.2 Pyrolysis of alkanes: Cracking
2.5.3 Halogenation of alkanes
2.6 Occurrence and Uses of Alkanes
2.6.1 Sources of alkanes: petroleum
2.6.2 Petroleum refining
2.6.3 Cracking
Extending reading: Jacobus Henricus van』t Hoff
Problems
Chapter 3 Alkenes
3.1 Structure of Alkenes
3.2 Nomenclature and Geometric Isomerism of Alkenes
3.2.1 Nomenclature of alkenes
3.2.2 Geometric isomerism of alkenes and its nomenclature
3.3 Physical Properties of Alkenes
3.4 Preparation and Uses of Alkenes
3.4.1 Dehydration
3.4.2 Dehydrohalogenation
3.4.3 Cracking
3.4.4 Use of alkenes
3.5 Chemical Properties of Alkenes
3.5.1 Catalytic hydrogenation reaction
3.5.2 Electrophilic addition to alkenes
3.5.3 HBr free radical addition
3.5.4 Addition of diboranes
3.5.5 Reactions of alkenes with oxygen electrophiles
3.5.6 The reaction of α-H
3.6 Polymer and Plastics
Extending reading: Synthesis of Palytoxin
Problems
Chapter 4 Dienes and Conjugation
4.1 Nomenclature of Dienes
4.2 Structure and Stability of Conjugated Dienes
4.2.1 Conjugative effect
4.2.2 Molecular orbital (MO) of 1,3-butadiene
4.3 Chemical Properties of Conjugative Dienes
4.3.1 Electrophile addition
4.3.2 Diels-Alder reaction
4.4 Rubber
Extending reading 1: Otto Paul Hermann Diels
Extending reading 2: Kurt Alder
Problems
Chapter 5 Cycloalkanes
5.1 Nomenclature of Cycloalkanes
5.1.1 Nomenclature of monocycloalkanes
5.1.2 Nomenclature of polycycloalkanes
5.2 Stabilities of Cycloalkanes
5.3 Structures and Conformation of Cycloalkanes
5.3.1 Structures and conformation of cyclopropane and cyclobutane
5.3.2 Structures and conformation of cyclopentane
5.3.3 Structures and conformation of cyclohexane
5.3.4 Conformations of higher cycloalkanes
5.3.5 Substituted cyclohexanes: axial and equatorial hydrogen atoms
5.4 Chemical Properties of Cycloalkanes
Extending reading: Derek Harold Richard Barton
Problems
Chapter 6 Alkynes
6.1 Structure of Alkynes
6.2 Nomenclature of Alkynes
6.3 Physical Properties of Alkynes
6.4 Preparation and Uses of Alkynes
6.4.1 Preparation of ethyne (HC≡CH)
6.4.2 By elimination reaction
6.5 Chemical Properties of Alkynes
6.5.1 Acidity of terminal alkynes
6.5.2 Addition by electrophilic reagents
6.5.3 Hydroboration/oxidation of alkynes
6.5.4 Reduction of alkynes
6.5.5 Oxidation of alkynes
6.5.6 Alkynes anions as nucleophiles
Extending reading: Discovery of Acetylene
Problems
Chapter 7 Stereochemistry
7.1 Enantiomerism and Chirality
7.2 Plane Polarized Light, Optical Activity and Specific Rotation
7.3 Fischer Projection
7.4 Configuration Representation Method, Configuration Labeling and Isomer Naming
7.4.1 R/S absolute configuration representation
7.4.2 D/L Relative configuration representation
7.5 Diastereomers
7.6 Resolution of Racemates
Extending reading: The Critical Role of Stereochemistry in Organic Chemistry — Insights from the Thalidomide Tragedy
Problems
Chapter 8 Alkyl Halides
8.1 Classification and Nomenclature of Halogenated Hydrocarbons
8.2 Structure of Halides
8.3 Physical Properties of Halides
8.4 Chemical Properties of Halogenated Hydrocarbons
8.4.1 Nucleophilic substitution reaction
8.4.2 Elimination reactions of alkyl halides
8.4.3 Organometallic compounds and their reactions
8.5 Reaction Mechanism and Influencing Factors of Nucleophilic Substitution Reaction
8.5.1 The mechanism for SN2 reaction
8.5.2 The mechanism for SN1 reaction
8.5.3 Factors affecting the rates of SN1 and SN2 reactions
8.6 Mechanisms of Dehydrohalogenation
8.6.1 Bimolecular elimination reaction: E2 reaction
8.6.2 Unimolecular elimination reaction: E1 reaction
8.7 Substitution versus Elimination
8.7.1 SN2 versus E
8.7.2 Tertiary halides: SN1 versus E
8.8 Halogenated Alkenes
8.8.1 Vinyl halogenated alkenes
8.8.2 Allyl halide alkenes
8.9 Commonly Halogenated Hydrocarbons
Extending reading: Paul Walden
Problems
Chapter 9 Benzene and Aromatic Chemistry
9.1 Structure of Benzene and Aromaticity
9.1.1 Kekul? and the structure of benzene
9.1.2 A resonance of bonding in benzene
9.1.3 The stability of benzene
9.1.4 The molecular orbitals of benzene
9.2 Nomenclature of Benzene Derivatives
9.3 Physical Properties of Benzene Derivatives
9.4 Chemical Properties of Benzene Derivatives
9.4.1 Reduction
9.4.2 Oxidation of alkyl side-chains
9.4.3 Free-radical halogenation of alkylbenzenes
9.5 Electrophilic Aromatic Substitution Reactions of Substituted Benzenes
9.5.1 Ortho, para-directing groups
9.5.2 Meta-directing groups
9.6 Polycyclic Aromatic Compounds
9.6.1 Non-fused polycyclic aromatic hydrocarbons
9.6.2 Fused polycyclic aromatic hydrocarbons
9.7 Non-Benzene Aromatic Hydrocarbons
9.7.1 H?ckel rule
9.7.2 Cyclobutadiene and cyclooctatetraene
9.7.3 Annulene
9.7.4 Cyclopentadiene and cycloheptatriene
Extending reading: Discovery of Benzene and the Theory of Molecular Structure of Benzene
Problems
Chapter 10 Alcohols, Phenols and Ethers
10.1 Structure of Alcohols, Phenols and Ethers
10.1.1 Structure of alcohols
10.1.2 Structure of phenols
10.1.3 Structure of ethers
10.2 Nomenclature of Alcohols, Phenols and Ethers
10.2.1 Nomenclature of alcohols
10.2.2 Nomenclature of phenols
10.2.3 Nomenclature of ethers
10.3 Physical Properties of Alcohols, Phenols and Ethers
10.3.1 Physical properties of alcohols
10.3.2 Physical properties of phenols
10.3.3 Physical properties of ethers
10.4 Preparation and Uses of Alcohols
10.4.1 Synthesis of alcohols by hydration of alkenes
10.4.2 Synthesis of alcohols by addition to carbonyl groups
10.4.3 Synthesis of alcohols by reduction of carbonyl-containing compounds
10.5 Chemical Properties of Alcohols
10.5.1 Acidity of alcohols
10.5.2 Conversion to alkyl halides
10.5.3 Dehydration of alcohols
10.5.4 Esterification of alcohols
10.5.5 Oxidation of alcohols
10.6 Preparation and Uses of Phenols
10.6.1 Laboratory synthesis
10.6.2 Industrial synthesis
10.7 Chemical Properties of Phenols
10.7.1 Acidity of phenols
10.7.2 Other reaction of the OH group of phenols
10.7.3 Reaction of the benzene ring of phenols
10.8 Preparation of Ethers
10.9 Chemical Properties of Ethers
10.9.1 The formation of oxonium salts
10.9.2 Acid-catalyzed cleavage of ethers
10.9.3 Autoxidation of ethers
10.10 Thiols, Sulfides and Disulfides
Extending reading: Victor Grignard
Problems
Chapter 11 Nuclear Magnetic Resonance Spectroscopy
11.1 Principles of Nuclear Magnetic Resonance
11.1.1 Discovery of nuclear magnetic resonance
11.1.2 Spin phenomenon of atomic nucleus
11.1.3 The reasons of nuclear magnetic resonance
11.2 Chemical Shift
11.2.1 Definition of chemical shift
11.2.2 Shielding effect
11.2.3 Practical representation of chemical shift
11.2.4 Factors affecting chemical shift
11.3 Chemical Shifts of Characteristic Protons in 1H-NMR
11.4 Integration Curves and Peak Areas
11.5 Spin Coupling
11.5.1 The causes of spin coupling
11.5.2 Coupling constant (J)
11.5.3 The law of coupling and splitting
11.5.4 Spectrum analysis
11.6 NMR Instrument
11.7 Carbon Spectrum (13C-NMR)
Extended reading: Paul Lauterbur
Problems
Chapter 12 Infrared Spectroscopy
12.1 Theoretical Background
12.1.1 Introduction
12.1.2 Generation conditions of infrared absorption spectra
12.1.3 Molecular vibration
12.1.4 Vibrational forms of molecules
12.2 The Infrared Spectrometer
12.3 Characteristic Absorption of Functional Groups
12.3.1 The functional group and fingerprint regions
12.3.2 Characteristic infrared absorption bands
12.3.3 The intensity of absorption bands
12.3.4 The infrared spectra of alkane, haloalkane, alkene, benzene and alcohol
12.4 Identifying Infrared Spectra
Extended reading: Kirchhoff and Bunsen on Spectroscopy
Problems
Chapter 13 Aldehydes and Ketones
13.1 Structure and Nomenclature of Aldehydes and Ketones
13.1.1 Structure and bonding of carbonyl group
13.1.2 Nomenclature of aldehydes and ketones
13.1.3 Physical properties
13.2 Preparation of Aldehydes and Ketones
13.2.1 Oxidation of alcohols (dehydrogenation)
13.2.2 Oxidation of alkenes (ozonolysis)
13.2.3 Hydrolysis of gem-dihalides
13.2.4 Hydration of alkynes
13.2.5 Friedel-Crafts acylation
13.2.6 Hydroformylation of the linear α-olefins
13.2.7 Oxidation of side chain of arenes
13.3 Reactions of Aldehydes and Ketones
13.3.1 Nucleophilic addition
13.3.2 The activity of α-hydrogen in aldehydes and ketones
13.3.3 Oxidation reactions
13.3.4 Reduction
13.4 α,β-Unsaturated Carbonyl Compounds
Extended reading: Organic Chemist Huang Minglong
Problems
Chapter 14 Carboxylic Acids and Acid Derivatives
14.1 Nomenclature of Carboxylic Acids and Their Derivatives
14.1.1 Nomencalture of carboxylic acids
14.1.2 Nomenclature of carboxylic acid derivatives
14.2 Structure and Physical Properties of Carboxylic Acids and Their Derivatives
14.2.1 Structure of carboxylic acids and their derivatives
14.2.2 Physical properties of carboxylic acids and their derivatives
14.3 Preparation of Carboxylic Acids
14.3.1 Oxidation reaction
14.3.2 Hydrolysis of carboxylic acid derivatives
14.3.3 Reaction of organometallic compounds with carbon dioxide
14.3.4 Other methods
14.4 Acidity of Carboxylic Acids
14.5 Formation of Acid Halides and Anhydrides
14.5.1 Formation of acid halides
14.5.2 Formation of acid anhydrides
14.6 Hydrolysis of Carboxylic Acid Derivatives
14.6.1 Hydrolysis reaction
14.6.2 Hydrolysis reaction mechanism
14.7 Alcoholysis of Carboxylic Acid Derivatives
14.7.1 Acylation
14.7.2 Transesterification
14.7.3 Esterification reaction mechanism
14.8 Aminolysis of Carboxylic Acid Derivatives
14.8.1 Reaction of carboxylic acid derivatives with amines
14.8.2 Nucleophilic substitution reaction mechanism of amines
14.9 Reaction of Carboxylic Acid Derivatives with Metal Reagents
14.9.1 Reaction with metal magnesium reagents
14.9.2 Reaction with metal lithium reagents
14.9.3 Reaction with metal copper-lithium reagents
14.9.4 Reaction with metal cadmium reagents
14.10 Reductions of Carboxylic Acids and Their Derivatives
14.10.1 Reduction of carboxylic acids
14.10.2 Reduction of acid halides
14.10.3 Reduction of esters
14.10.4 Reduction of amides
14.10.5 Reduction of nitriles
14.11 Other Reactions of Carboxylic Acids and Their Derivatives
14.11.1 Decarboxylation reaction
14.11.2 α-Substituted carboxylic acids and their derivatives
14.11.3 Elimination reaction of esters
14.11.4 Hoffmann degradation reaction of amides
14.12 Lactones
14.13 Lipids and Waxes
14.14 Carbonic Acid Derivatives
14.15 Surfactants and Soaps
Extended reading 1: August Wilhelm von Hofmann
Extended reading 2: Aspirin (acetylsalicylic acid)
Problems
Chapter 15 Difunctional Compounds
15.1 Introduction
15.2 Hydroxy Aldehydes and Ketones
15.2.1 Properties
15.2.2 Preparation
15.2.3 Reactions
15.3 Hydroxy Acids
15.3.1 Properties
15.3.2 Preparation
15.3.3 Dehydration of hydroxy acid
15.4 Dicarboxylic Acids
15.4.1 Property and reactions
15.4.2 Acidity of dicarboxylic acids
15.5 Dicarbonyl Compounds
15.5.1 Acidity of β-dicarbonyl compounds and stability of enol anion
15.5.2 Diethyl malonate
15.5.3 Ethyl acetoacetate
15.5.4 Michael addition reaction
15.6 Summary
Extended reading: Possible Substitutes for White Pollution—Lactic Acid Polymer
Problems
Chapter 16 Amines and Other Nitrogen-Containing Compounds
16.1 Amines
16.1.1 Nomenclature
16.1.2 Structure and physical properties
16.1.3 Preparation
16.1.4 Chemical properties
16.1.5 Reactions of diazonium ions
16.2 Nitro Compounds
16.3 Nitriles
16.3.1 Nomenclature
16.3.2 Physical properties
16.3.3 Preparation
16.3.4 Reactions of nitriles
Extended reading: The Development of Nitroglycerin
Problems
Chapter 17 Heterocyclic Compounds
17.1 Heterocyclic System
17.2 Classification and Nomenclature of Heterocycles
17.3 Structure and Aromaticity of Heterocycles
17.4 Five-Membered Unsaturated Heterocycles
17.4.1 Furan
17.4.2 Thiophene
17.4.3 Pyrrole
17.4.4 Indole
17.5 Six-Membered Unsaturated Heterocycles
17.6 Quinoline and Isoquinoline
17.6.1 Quinoline
17.6.2 Isoquinoline
Extended reading: Tu Youyou and Artemisinin
Problems
Chapter 18 Carbohydrates and Nucleic Acids
18.1 Stereochemistry of Sugars
18.1.1 The D and L notation
18.1.2 Configurations of aldoses
18.1.3 Configurations of ketoses
18.2 Structure of Glucose
18.3 Reactions of Monosaccharides
18.3.1 Reduction
18.3.2 Oxidation
18.3.3 Osazone formation
18.3.4 Ester formation
18.3.5 Chain elongation
18.3.6 Chain shortening
18.4 Disaccharides
18.5 Polysaccharides
Extended reading: Hermann Emil Fischer
Problems
Chapter 19 Amino Acids, Peptides, Proteins and Nucleic Acids
19.1 Amino Acids
19.1.1 Nomenclature of amino acids
19.1.2 Physical properties of amino acids
19.1.3 The acidity and alkalinity of amino acids
19.1.4 Amino acid reaction
19.1.5 Amino acid synthesis
19.2 Peptides and Proteins
19.2.1 Peptide nomenclature
19.2.2 Synthesis of peptides and proteins
19.2.3 Determination of polypeptide structure
19.2.4 Protein hierarchy
19.3 Enzyme
19.4 Nucleic Acid
Extended reading: Human Genome Project
Problems
Chapter 20 Organometallic Compounds
20.1 Preparation of Organometallic Compounds
20.1.1 Preparation of organolithium compounds
20.1.2 Preparation of organomagnesium compounds
20.1.3 Preparation of organocopper compounds
20.1.4 Preparation of organozinc compounds
20.2 Main Reactions of Organometallic Compounds
20.2.1 Organometallic compounds as Brnsted bases
20.2.2 Organometallic compounds as nucleophilic reagents
Extended reading: Karl Ziegler
Problems
Chapter 21 Orbitals and Organic Chemistry: Pericyclic Reactions
21.1 Introduction
21.1.1 Evolution of the theory of concerted reactions
21.1.2 A review of π molecular orbitals
21.1.3 Interactions between molecular orbitals
21.2 Electrocyclic Reaction
21.3 Cycloaddition Reaction
21.3.1 Photochemical dimerization of alkenes
21.3.2 Diels-Alder reaction
21.4 Sigmatropic Rearrangements
Extended reading: Robert Burns Woodward
Problems
Reference
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