本书是LGWade和JWSimek编写的Organic Chemistry (Ninth Edition) 的改编版，是根据教育部关于高等学校本科教学质量工程要重视双语教学的文件精神，选择国外优秀英文原版有机化学教材，结合双语教学的实践经验改编而成的双语教材。全书共26章，涵盖内容与国内高等学校化学、化工类有机化学教材基本一致，包括有机化学概论、有机化合物命名、立体化学、结构表征、烃及卤代烃、含氧化合物、含氮化合物、天然有机化合物等内容。每章后有中文概要，书后附有索引。

本书可作为化学化工专业的有机化学双语教材，亦可作为其他相关专业的教学参考书，可使学生在学习有机化学基础知识的同时提高专业英语水平。

前辅文
Chapter 1　Structure and Bonding
  Goals for Chapter 1
  1-1　The Origins of Organic Chemistry
  1-2　Principles of Atomic Structure
  1-3　Bond Formation： The Octet Rule
  1-4　Lewis Structures
  1-5　Multiple Bonding
  1-6　Electronegativity and Bond Polarity
  1-7　Formal Charges
  1-8　Ionic Structures
  1-9　Resonance
  1-10　Structural Formulas
  1-11　Molecular Formulas and Empirical Formulas
  1-12　Wave Properties of Electrons in Orbitals
  1-13　Molecular Orbitals
  1-14　Pi Bonding
  1-15　Hybridization and Molecular Shapes
  1-16　Drawing ThreeDimensional Molecules
  1-17　General Rules of Hybridization and Geometry
  1-18　Bond Rotation
  1-19　Isomerism
  Summary in Chinese
  Study Problems
Chapter 2　Acids and Bases
  Goals for Chapter 2
  2-1　Polarity of Bonds and Molecules
  2-2　Intermolecular Forces
  2-3　Polarity Effects on Solubilities
  2-4　Arrhenius Acids and Bases
  2-5　BrnstedLowry Acids and Bases
  2-6　Strengths of Acids and Bases
  2-7　Equilibrium Positions of AcidBase Reactions
  2-8　Solvent Effects on Acidity and Basicity
  2-9　Effects of Size and Electronegativity on Acidity
  2-10　Inductive Effects on Acidity
  2-11　Hybridization Effects on Acidity
  2-12　Resonance Effects on Acidity and Basicity
  2-13　Lewis Acids and Bases
  2-14　The CurvedArrow Formalism
  Summary in Chinese
  Study Problems
Chapter 3　Functional Groups and Nomenclature of Organic Compounds
  Goals for Chapter 3
  3-1　Hydrocarbons
  3-2　Organic Compounds Containing Oxygen
  3-3　Organic Compounds Containing Nitrogen
  3-4　Nomenclature of Alkanes
  3-5　Nomenclature of Cycloalkanes
  3-6　Nomenclature of Alkenes
  3-7　Nomenclature of Alkynes
  3-8　Nomenclature of Benzene Derivatives
  3-9　Nomenclature of Alkyl Halides
  3-10　Nomenclature of Alcohols,Phenols and Thiols
  3-11　Nomenclature of Ethers and Sulfides
  3-12　Nomenclature of Amines
  3-13　Nomenclature of Ketones and Aldehydes
  3-14　Nomenclature of Carboxylic Acids
  3-15　Structure and Nomenclature of Acid Derivatives
  Summary in Chinese
  Study Problems
Chapter 4　Structure and Stereochemistry of Alkanes
  Goals for Chapter 4
  4-1　Physical Properties of Alkanes
  4-2　Uses and Sources of Alkanes
  4-3　Reactions of Alkanes
  4-4　Structure and Conformations of Alkanes
  4-5　Physical Properties and Stabilities of Cycloalkanes
  4-6　Cyclohexane Conformations
  4-7　Conformations of Monosubstituted Cyclohexanes
  4-8　Conformations of Disubstituted Cyclohexanes
  4-9　Decalin Conformations
  Summary in Chinese
  Study Problems
Chapter 5　The Study of Chemical Reactions
  Goals for Chapter 5
  5-1　Introduction
  5-2　Chlorination of Methane
  5-3　The FreeRadical Chain Reaction
  5-4　Equilibrium Constants and Free Energy
  5-5　Enthalpy and Entropy
  5-6　BondDissociation Enthalpies
  5-7　Enthalpy Changes in Chlorination
  5-8　Kinetics and the Rate Equation
  5-9　Activation Energy and the Temperature Dependence of Rates
  5-10　Transition States
  5-11　Rates of Multistep Reactions
  5-12　Temperature Dependence of Halogenation
  5-13　Selectivity in Halogenation
  5-14　Hammond’s Postulate
  5-15　Radical Inhibitors
  5-16　Reactive Intermediates
  Summary in Chinese
  Study Problems
Chapter 6　Stereochemistry
  Goals for Chapter 6
  6-1　Introduction
  6-2　Chirality
  6-3　（R） and (S) Nomenclature of Asymmetric Carbon Atoms
  6-4　Optical Activity
  6-5　Biological Discrimination of Enantiomers　　
  6-6　Racemic Mixtures
  6-7　Enantiomeric Excess and Optical Purity
  6-8　Chirality of Conformationally Mobile Systems
  6-9　Chiral Compounds without Asymmetric Atoms
  6-10　Fischer Projections
  6-11　Diastereomers
  6-12　Stereochemistry of Molecules with Two or More Asymmetric Carbons
  6-13　Meso Compounds
  6-14　Absolute and Relative Configuration
  6-15　Physical Properties of Diastereomers
  6-16　Resolution of Enantiomers
  Summary in Chinese
  Study Problems
Chapter 7　Alkyl Halides: Nucleophilic Substitution and Elimination
  Goals for Chapter 7
  7-1　Introduction
  7-2　Common Uses of Alkyl Halides
  7-3　Structure of Alkyl Halides
  7-4　Physical Properties of Alkyl Halides
  7-5　Preparation of Alkyl Halides
  7-6　Reactions of Alkyl Halides: Substitution and Elimination
  7-7　Bimolecular Nucleophilic Substitution: The SN2 Reaction
  7-8　Generality of the SN2 Reaction
  7-9　Factors Affecting SN2 Reactions: Strength of the Nucleophile
  7-10　Reactivity of the Substrate in SN2 Reactions
  7-11　Stereochemistry of the SN2 Reaction
  7-12　Unimolecular Nucleophilic Substitution: The SN1 Reaction
  7-13　Stereochemistry of the SN1 Reaction
  7-14　Rearrangements in SN1 Reactions
  7-15　Comparison of SN1 and SN2 Reactions
  7-16　Elimination:E1 and E2 Reaction
  7-17　Unimolecular Elimination:The E1 Reaction
  7-18　Positional Orientation of Elimination: Zaitsevs Rule
  7-19　Bimolecular Elimination: The E2 Reaction
  7-20　Bulky Bases in E2 Eliminations; Hofmann Orientation
  7-21　Stereochemistry of the E2 Reaction
  7-22　E2 Reactions in Cyclohexane Systems
  7-23　Comparison of E1 and E2 Elimination Mechanisms
  7-24　Competition Between Substitutions and Eliminations
  Summary in Chinese
  Study Problems
Chapter 8　Structure and Synthesis of Alkenes
  Goals for Chapter 8
  8-1　Introduction
  8-2　The Orbital Description of the Alkene Double Bond
  8-3　Elements of Unsaturation
  8-4　Commercial Importance of Alkenes
  8-5　Physical Properties of Alkenes
  8-6　Stability of Alkenes
  8-7　Alkene Synthesis by Elimination of Alkyl Halides
  8-8　Alkene Synthesis by Dehydration of Alcohols
  8-9　Alkene Synthesis by HighTemperature Industrial Methods
  Summary in Chinese
  Study Problems
Chapter 9　Reactions of Alkenes
  Goals for Chapter 9
  9-1　Reactivity of the CarbonCarbon Double Bond
  9-2　Electrophilic Addition to Alkenes
  9-3　Addition of Hydrogen Halides to Alkenes
  9-4　Addition of Water: Hydration of Alkenes
  9-5　Hydration by OxymercurationDemercuration
  9-6　AlkoxymercurationDemercuration
  9-7　Hydroboration of Alkenes
  9-8　Addition of Halogens to Alkenes
  9-9　Formation of Halohydrins
  9-10　Catalytic Hydrogenation of Alkenes
  9-11　Addition of Carbenes to Alkenes
  9-12　Epoxidation of Alkenes
  9-13　AcidCatalyzed Opening of Epoxides
  9-14　Syn Dihydroxylation of Alkenes
  9-15　Oxidative Cleavage of Alkenes
  9-16　Polymerization of Alkenes
  9-17　Olefin Metathesis
  Summary in Chinese
  Study Problems
Chapter 10　Alkynes
  Goals for Chapter 10
  10-1　Introduction
  10-2　Physical Properties of Alkynes
  10-3　Commercial Importance of Alkynes
  10-4　Electronic Structure of Alkynes
  10-5　Acidity of Alkynes: Formation of Acetylide Ions
  10-6　Synthesis of Alkynes from Acetylides
  10-7　Synthesis of Alkynes by Elimination Reactions
  10-8　Addition Reactions of Alkynes
  10-9　Oxidation of Alkynes
  Summary in Chinese
  Study Problems
Chapter 11　Conjugated Systems and OrbitalSymmetry
  Goals for Chapter 11
  11-1　Stabilities of Dienes
  11-2　Molecular Orbital Picture of a Conjugated System
  11-3　Allylic Cations
  11-4　1,2 and 1,4Addition to Conjugated Dienes
  11-5　Kinetic versus Thermodynamic Control in the Addition of HBr to Buta1,3diene
  11-6　Allylic Radicals
  11-7　Molecular Orbitals of the Allylic System
  11-8　Electronic Configurations of the Allyl Radical, Cation, and Anion
  11-9　SN2 Displacement Reactions of Allylic Halides and Tosylates
  11-10　The DielsAlder Reaction
  11-11　The DielsAlder as an Example of a Pericyclic Reaction
  Summary in Chinese
  Study Problems
Chapter 12　Infrared and Ultraviolet Spectroscopy
  Goals for Chapter 12
  12-1　Introduction
  12-2　The Electromagnetic Spectrum
  12-3　The Infrared Region
  12-4　Molecular Vibrations
  12-5　IRActive and IRInactive Vibrations
  12-6　Measurement of the IR Spectrum
  12-7　Infrared Spectroscopy of Hydrocarbons
  12-8　Characteristic Absorptions of Alcohols and Amines
  12-9　Characteristic Absorptions of Carbonyl Compounds
  12-10　Characteristic Absorptions of C—N Bonds
  12-11　Simplified Summary of IR Stretching Frequencies
  12-12　Reading and Interpreting IR Spectra
  12-13　Ultraviolet Absorption Spectroscopy
  12-14　Interpreting UVVisible Spectra
  12-15　Colored Organic Compounds
  Summary in Chinese
  Study Problems
Chapter 13　Nuclear Magnetic Resonance Spectroscopy and Mass Spectrometry
  Goals for Chapter 13
  13-1　Introduction to Nuclear Magnetic Resonance Spectroscopy
  13-2　Theory of Nuclear Magnetic Resonance
  13-3　Magnetic Shielding by Electrons
  13-4　The NMR Spectrometer
  13-5　The Chemical Shift
  13-6　The Number of Signals
  13-7　Areas of the Peaks
  13-8　SpinSpin Splitting
  13-9　Carbon13 NMR Spectroscopy
  13-10　Interpreting Carbon NMR Spectra
  13-11　Introduction to Mass Spectrometry
  13-12　Determination of the Molecular Formula by Mass Spectrometry
  13-13　Fragmentation Patterns in Mass Spectrometry
  Summary in Chinese
  Study Problems
Chapter 14　Structure and Synthesis of Alcohols
  Goals for Chapter 14
  14-1　Introduction
  14-2　Structure and Classification of Alcohols
  14-3　Physical Properties of Alcohols
  14-4　Commercially Important Alcohols
  14-5　Acidity of Alcohols and Phenols
  14-6　Organometallic Reagents for Alcohol Synthesis
  14-7　Reactions of Organometallic Compounds
  14-8　Side Reactions of Organometallic Reagents: Reduction of Alkyl Halides
  14-9　Reduction of the Carbonyl Group: Synthesis of 1° and 2° Alcohols
  14-10　Thiols (Mercaptans)
  Summary in Chinese
  Study Problems
Chapter 15　Reactions of Alcohols
  Goals for Chapter 15
  15-1　Oxidation States of Alcohols and Related Functional Groups
  15-2　Oxidation of Alcohols
  15-3　Additional Methods for Oxidizing Alcohols
  15-4　Alcohols as Nucleophiles and Electrophiles; Formation of Tosylates
  15-5　Reduction of Alcohols
  15-6　Reactions of Alcohols with Hydrohalic Acids
  15-7　Reactions of Alcohols with Phosphorus Halides
  15-8　Reactions of Alcohols with Thionyl Chloride
  15-9　Dehydration Reactions of Alcohols
  15-10　Unique Reactions of Diols
  15-11　Esterification of Alcohols
  15-12　Reactions of Alkoxides
  Summary in Chinese
  Study Problems
Chapter 16　Ethers,Epoxides,and Thioethers
  Goals for Chapter 16
  16-1　Introduction
  16-2　Physical Properties of Ethers
  16-3　Spectroscopy of Ethers
  16-4　Synthesis of Ethers
  16-5　Cleavage of Ethers by HBr and HI
  16-6　Autoxidation of Ethers
  16-7　Synthesis of Epoxides
  16-8　AcidCatalyzed Ring Opening of Epoxides
  16-9　BaseCatalyzed Ring Opening of Epoxides
  16-10　Orientation of Epoxide Ring Opening
  16-11　Reactions of Epoxides with Grignard and Organolithium Reagents
  16-12　Epoxy Resins: The Advent of Modern Glues
  16-13　Thioethers (Sulfides) and Silyl Ethers
  Summary in Chinese
  Study Problems
Chapter 17　Aromatic Compounds
  Goals for Chapter 17
  17-1　Introduction: The Discovery of Benzene
  17-2　The Structure and Properties of Benzene
  17-3　The Molecular Orbital Picture of Benzene
  17-4　Aromatic, Antiaromatic, and Nonaromatic Compounds
  17-5　Hückels Rule
  17-6　Molecular Orbital Derivation of Hückels Rule
  17-7　Aromatic lons
  17-8　Heterocyclic Aromatic Compounds
  17-9　Polynuclear Aromatic Hydrocarbons
  17-10　Aromatic Allotropes of Carbon
  17-11　Fused Heterocyclic Compounds
  17-12　Physical Properties of Benzene and Its Derivatives
  17-13　Spectroscopy of Aromatic Compounds
  Summary in Chinese
  Study Problems
Chapter 18　Reactions of Aromatic Compounds
  Goals for Chapter 18
  18-1　Electrophilic Aromatic Substitution
  18-2　Halogenation of Benzene
  18-3　Nitration of Benzene
  18-4　Sulfonation of Benzene
  18-5　Nitration of Toluene: The Effect of Alkyl Substitution
  18-6　Activating, Ortho, ParaDirecting Substituents
  18-7　Deactivating, MetaDirecting Substituents
  18-8　Halogen Substituents: Deactivating, but Ortho, ParaDirecting
  18-9　Effects of Multiple Substituents on Electrophilic Aromatic Substitution
  18-10　The FriedelCrafts Alkylation
  18-11　The FriedelCrafts Acylation
  18-12　Nucleophilic Aromatic Substitution
  18-13　Aromatic Substitutions Using Organometallic Reagents
  18-14　Addition Reactions of Benzene Derivatives
  18-15　SideChain Reactions of Benzene Derivatives
  18-16　Reactions of Phenols
  Summary in Chinese
  Study Problems
Chapter 19　Ketones and Aldehydes
  Goals for Chapter 19
  19-1　Carbonyl Compounds
  19-2　Structure of the Carbonyl Group
  19-3　Physical Properties of Ketones and Aldehydes
  19-4　Spectroscopy of Ketones and Aldehydes
  19-5　Industrial Importance of Ketones and Aldehydes
  19-6　Review of Syntheses of Ketones and Aldehydes
  19-7　Reactions of Ketones and Aldehydes: Nucleophilic Addition
  19-8　Hydration of Ketones and Aldehydes
  19-9　Formation of Acetals
  19-10　Formation of Cyanohydrins
  19-11　Formation of Imines
  19-12　Condensations with Hydroxylamine and Hydrazines
  19-13　The Wittig Reaction
  19-14　Oxidation of Aldehydes
  19-15　Reductions of Ketones and Aldehydes
  Summary in Chinese
  Study Problems
Chapter 20　Amines
  Goals for Chapter 20
  20-1　Introduction
  20-2　Structure of Amines
  20-3　Physical Properties of Amines
  20-4　Basicity of Amines
  20-5　Factors that Affect Amine Basicity
  20-6　Salts of Amines
  20-7　Amine Salts as PhaseTransfer Catalysts
  20-8　Spectroscopy of Amines
  20-9　Aromatic Substitution of Arylamines and Pyridine
  20-10　Alkylation of Amines by Alkyl Halides
  20-11　Acylation of Amines by Acid Chlorides
  20-12　Formation of Sulfonamides
  20-13　Amines as Leaving Groups: The Hofmann Elimination
  20-14　Oxidation of Amines: The Cope Elimination
  20-15　Reactions of Amines with Nitrous Acid
  20-16　Reactions of Arenediazonium Salts
  20-17　Synthesis of Amines by Reductive Amination
  20-18　Synthesis of Amines by AcylationReduction
  20-19　Syntheses Limited to Primary Amines
  Summary in Chinese
  Study Problems
Chapter 21　Carboxylic Acids
  Goals for Chapter 21
  21-1　Introduction
  21-2　Structure and Physical Properties of Carboxylic Acids
  21-3　Acidity of Carboxylic Acids
  21-4　Salts of Carboxylic Acids
  21-5　Commercial Sources of Carboxylic Acids
  21-6　Spectroscopy of Carboxylic Acids
  21-7　Synthesis of Carboxylic Acids
  21-8　Condensation of Acids with Alcohols: The Fischer Esterification
  21-9　Esterification Using Diazomethane
  21-10　Condensation of Acids with Amines: Direct Synthesis of Amides
  21-11　Formation of Acid Chlorides
  21-12　Reduction of Carboxylic Acids to Form Alcohols
  21-13　Alkylation of Carboxylic Acids to Form Ketones
  Summary in Chinese
  Study Problems
Chapter 22　Carboxylic Acid Derivatives
  Goals for Chapter 22
  22-1　Introduction
  22-2　Physical Properties of Carboxylic Acid Derivatives
  22-3　Spectroscopy of Carboxylic Acid Derivatives
  22-4　Interconversion of Acid Derivatives by Nucleophilic Acyl Substitution
  22-5　Transesterification
  22-6　Hydrolysis of Carboxylic Acid Derivatives
  22-7　Reduction of Acid Derivatives
  22-8　Reactions of Acid Derivatives with Organometallic Reagents
  22-9　Esters and Amides of Carbonic Acid
  Summary in Chinese
  Study Problems
Chapter 23　Condensations and Alpha Substitutions of Carbonyl Compounds
  Goals for Chapter 23
  23-1　Introduction
  23-2　Enols and Enolate Ions
  23-3　Alpha Halogenation of Ketones
  23-4　Alpha Bromination of Acids: The HVZ Reaction
  23-5　Alkylation of Enolate Ions
  23-6　Formation and Alkylation of Enamines
  23-7　The Aldol Condensation of Ketones and Aldehydes
  23-8　Dehydration of Aldol Products
  23-9　Crossed Aldol Condensations
  23-10　Aldol Cyclizations
  23-11　The Claisen Ester Condensation
  23-12　The Dieckmann Condensation: A Claisen Cyclization
  23-13　Crossed Claisen Condensations
  23-14　Syntheses Using β Dicarbonyl Compounds
  23-15　The Malonic Ester Synthesis
  23-16　The Acetoacetic Ester Synthesis
  23-17　Conjugate Additions: The Michael Reaction
  23-18　The Robinson Annulation
  Summary in Chinese
  Study Problems
Chapter 24　Carbohydrates and Nucleic Acids
  Goals for Chapter 24
  24-1　Introduction
  24-2　Classification of Carbohydrates
  24-3　Monosaccharides
  24-4　Cyclic Structures of Monosaccharides
  24-5　Anomers of Monosaccharides: Mutarotation
  24-6　Reactions of Monosaccharides: Reduction
  24-7　Oxidation of Monosaccharides: Reducing Sugars
  24-8　Nonreducing Sugars: Formation of Glycosides
  24-9　Ether and Ester Formation
  24-10　Reactions with Phenylhydrazine: Osazone Formation
  24-11　Chain Shortening: The Ruff Degradation
  24-12　Chain Lengthening: The KilianiFischer Synthesis
  24-13　Disaccharides
  24-14　Polysaccharides
  24-15　Nucleic Acids: Introduction
  24-16　Ribonucleosides and Ribonucleotides
  24-17　The Structures of RNA and DNA
  24-18　Additional Functions of Nucleotides
  Summary in Chinese
  Study Problems
Chapter 25　Amino Acids,Peptides, and Proteins
  Goals for Chapter 25
  25-1　Introduction
  25-2　Structure and Stereochemistry of the α Amino Acids
  25-3　AcidBase Properties of Amino Acids
  25-4　Isoelectric Points
  25-5　Synthesis of Amino Acids
  25-6　Resolution of Amino Acids
  25-7　Reactions of Amino Acids
  25-8　Structure and Nomenclature of Peptides and Proteins
  25-9　Peptide Structure Determination
  25-10　Laboratory Peptide Synthesis
  25-11　Classification of Proteins
  25-12　Levels of Protein Structure
  25-13　Protein Denaturation
  Summary in Chinese
  Study Problems
Chapter 26　Lipids
  Goals for Chapter 26
  26-1　Introduction
  26-2　Waxes
  26-3　Triglycerides
  26-4　Saponification of Fats and Oils: Soaps and Detergents
  26-5　Phospholipids
  26-6　Steroids
  26-7　Terpenes
  Summary in Chinese
  Study Problems
Brief Answers to Selected Problems
Index
Appendixes

“十二五”普通高等教育本科国家级规划教材