本书是L G Wade 编写的Organic Chemistry (Sixth 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,书后附有索引和专业词汇中英文对照表｡
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｡
- 目录
- 前辅文
- Chapter 1 Introduction and Review
- 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 Arrhenius Acids and Bases
- 1-13 BrnstedLowry Acids and Bases
- 1-14 Lewis Acids and Bases
- Summary in Chinese
- Study Problems
- Chapter 2 Structure and Properties of Organic Molecules
- 2-1 Wave Properties of Electrons inOrbitals
- 2-2 Molecular Orbitals
- 2-3 Pi Bonding
- 2-4 Hybridization and Molecular Shapes
- 2-5 Drawing ThreeDimensionalMolecules
- 2-6 General Rules of Hybridization and Geometry
- 2-7 Bond Rotation
- 2-8 Isomerism
- 2-9 Polarity of Bonds and Molecules
- 2-10 Intermolecular Forces
- 2-11 Polarity Effects on Solubilities
- Summary in Chinese
- Study Problems
- Chapter 3 Brief Introduction and Nomenclature of Organic Compounds
- 3-1 Hydrocarbons
- 3-2 Organic Compounds Containing Oxygen
- 3-3 Organic Compounds Containing Nitrogen
- 3-4 Nomenclature of Alkanes
- 3-5 Nomenclature of Alkenes
- 3-6 Nomenclature of Alkynes
- 3-7 Nomenclature of Cycloalkanes
- 3-8 Nomenclature of Benzene Derivatives
- 3-9 Nomenclature of Alkyl Halides
- 3-10 Nomenclature of Alcohols 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
- 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 Cycloalkanes
- 4-6 Cyclohexane Conformations
- 4-7 Conformations of Monosubstituted Cyclohexanes
- 4-8 Conformations of Disubstituted Cyclohexanes
- Summary in Chinese
- Study Problems
- Chapter 5 The Study of ChemicalReactions
- 5-1 Introduction
- 5-2 Chlorination of Methane
- 5-3 The FreeRadical Chain Reaction
- 5-4 Equilibrium Constants and Free Energy
- 5-5 Enthalpy and Entropy
- 5-6 BondDissociation 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 The Hammond Postulate
- 5-15 Radical Inhibitors
- 5-16 Reactive Intermediates
- Summary in Chinese
- Study Problems
- Chapter 6 Stereochemistry
- 6-1 Introduction
- 6-2 Chirality
- 6-3 （R） and (S) Nomenclature of Asymmetric Carbon Atoms
- 6-4 Optical Activity
- 6-5 Racemic Mixtures
- 6-6 Enantiomeric Excess and Optical Purity
- 6-7 Chirality of Conformationally Mobile Systems
- 6-8 Chiral Compounds without Asymmetric Atoms
- 6-9 Fischer Projections
- 6-10 Diastereomers
- 6-11 Stereochemistry of Molecules with Two or More AsymmetricCarbons
- 6-12 Meso Compounds
- 6-13 Absolute and Relative Configuration
- 6-14 Physical Properties of Diastereomers
- 6-15 Resolution of Enantiomers
- Summary in Chinese
- Study Problems
- Chapter 7 Alkyl Halides: Nucleophilic Substitution and Elimination
- 7-1 Introduction
- 7-2 Common Uses of Alkyl Halides
- 7-3 Structure of Alkyl Halides
- 7-4 Physical Properties of AlkylHalides
- 7-5 Preparation of Alkyl Halides
- 7-6 Reactions of Alkyl Halides: Substitution and Elimination
- 7-7 SecondOrder Nucleophilic Substitution:The SN2 Reaction
- 7-8 Generality of the SN2 Reaction
- 7-9 Factors Affecting SN2 Reactions: Strength of the Nucleophile
- 7-10 Reactivity of the Substrate in SN2 Reactions
- 7-11 Stereochemistry of the SN2 Reaction
- 7-12 FirstOrder Nucleophilic Substitution: The SN1 Reaction
- 7-13 Stereochemistry of the SN1Reaction
- 7-14 Rearrangements in SN1 Reactions
- 7-15 Comparison of SN1 and SN2 Reactions
- 7-16 FirstOrder Elimination: The E1 Reaction
- 7-17 Positional Orientation of Elimination: Zaitsevs Rule
- 7-18 SecondOrder Elimination: The E2 Reaction
- 7-19 Stereochemistry of the E2 Reaction
- 7-20 Comparison of E1 and E2 EliminationMechanisms
- Summary in Chinese
- Study Problems
- Chapter 8 Structure and Synthesis ofAlkenes
- 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 Stability of Alkenes
- 8-6 Physical Properties of Alkenes
- 8-7 Alkene Synthesis by Elimination of Alkyl Halides
- 8-8 Alkene Synthesis by Dehydration of Alcohols
- 8-9 Alkene Synthesis by HighTemperature Industrial Methods
- Summary in Chinese
- Study Problems
- Chapter 9 Reactions of Alkenes
- 9-1 Reactivity of the CarbonCarbon DoubleBond
- 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 OxymercurationDemercuration
- 9-6 AlkoxymercurationDemercuration
- 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 AcidCatalyzed Opening of Epoxides
- 9-14 Syn Hydroxylation of Alkenes
- 9-15 Oxidative Cleavage of Alkenes
- 9-16 Polymerization of Alkenes
- Summary in Chinese
- Study Problems
- Chapter 10 Alkynes
- 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
- 11-1 Introduction
- 11-2 Stabilities of Dienes
- 11-3 Molecular Orbitals of aConjugated System
- 11-4 Allylic Cations
- 11-5 1, 2and 1, 4Addition to Conjugated Dienes
- 11-6 Kinetic versus Thermodynamic Controlin the Addition of HBr to 1, 3Butadiene
- 11-7 Allylic Radicals
- 11-8 Molecular Orbitals of the Allylic System
- 11-9 Electronic Configurations of the Allyl Radical, Cation, and Anion
- 11-10 SN2 Displacement Reactions of Allylic Halides and Tosylates
- 11-11 The DielsAlder Reaction
- 11-12 The DielsAlder as an Example of a Pericyclic Reaction
- Summary in Chinese
- Study Problems
- Chapter 12 Infrared and Ultraviolet Spectroscopy
- 12-1 Introduction
- 12-2 The Electromagnetic Spectrum
- 12-3 The Infrared Region
- 12-4 Molecular Vibrations
- 12-5 IRActive and IRInactive 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 Ultraviolet Light and Electronic Transitions
- 12-15 Measurement of the UVVisible Spectrum
- 12-16 Interpreting UVVisible Spectra
- Summary in Chinese
- Study Problems
- Chapter 13 Nuclear Magnetic ResonanceSpectroscopy and MassSpectrometry
- 13-1 Introduction to Nuclear Magnetic Resonance Spectroscopy
- 13-2 Theory of Nuclear MagneticResonance
- 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 SpinSpin 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
- 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 Synthesis of Alcohols: Addition of Organometallic Reagents to Carbonyl Compounds
- 14-8 Side Reactions of Organometallic Reagents:
- Reduction of Alkyl Halides
- 14-9 Synthesis of 1° and 2° Alcohols: Reduction of the Carbonyl
- Group
- 14-10 Thiols (Mercaptans)
- Summary in Chinese
- Study Problems
- Chapter 15 Reactions of Alcohols
- 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 Electro
- philes: 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 Sulfides
- 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 AcidCatalyzed Ring Opening of Epoxides
- 16-9 BaseCatalyzed 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 Sulfides (Thioethers)
- Summary in Chinese
- Study Problems
- Chapter 17 Aromatic Compounds
- 17-1 Introduction: The Discovery of Benzene
- 17-2 The Structure and Properties of Benzene
- 17-3 The Molecular Orbitals of Benzene
- 17-4 Aromatic, Antiaromatic, and Nonaromatic Compounds
- 17-5 Hückels Rule
- 17-6 Molecular Orbital Derivation of Hückels Rule
- 17-7 Aromatic Ions
- 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 AromaticCompounds
- 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, ParaDirecting Substituents
- 18-7 Deactivating, MetaDirecting Substituents
- 18-8 Halogen Substituents: Deactivating,but Ortho, ParaDirecting
- 18-9 Effects of Multiple Substituents on Electrophilic Aromatic Substitution
- 18-10 The FriedelCrafts Alkylation
- 18-11 The FriedelCrafts Acylation
- 18-12 Nucleophilic Aromatic Substitution
- 18-13 Addition Reactions of Benzene Derivatives
- 18-14 SideChain Reactions of Benzene Derivatives
- 18-15 Reactions of Phenols
- Summary in Chinese
- Study Problems
- Chapter 19 Ketones and Aldehydes
- 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 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 andAldehydes
- Summary in Chinese
- Study Problems
- Chapter 20 Amines
- 20-1 Introduction
- 20-2 Structure of Amines
- 20-3 Physical Properties of Amines
- 20-4 Basicity of Amines
- 20-5 Effects on Amine Basicity
- 20-6 Salts of Amines
- 20-7 Amine Salts as PhaseTransfer 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 AcylationReduction
- 20-19 Syntheses Limited to Primary Amines
- Summary in Chinese
- Study Problems
- Chapter 21 Carboxylic Acids
- 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
- 21-13 Alkylation of Carboxylic Acids to Form Ketones
- Summary in Chinese
- Study Problems
- Chapter 22 Carboxylic Acid Derivatives
- 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 CarbonylCompounds
- 23-1 Introduction
- 23-2 Enols and Enolate Ions
- 23-3 Alpha Halogenation of Ketones
- 23-4 α Bromination of Acids: The HVZ Reaction
- 23-5 Alkylation of Enolate Ions
- 23-6 Formation and Alkylation ofEnamines
- 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
- 2313 Crossed Claisen Condensations
- 23-14 Syntheses Using βDicarbonyl 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 NucleicAcids
- 24-1 Introduction
- 24-2 Classification of Carbohydrates
- 24-3 Monosaccharides
- 24-4 Erythro and Threo Diastereomers
- 24-5 Epimers
- 24-6 Cyclic Structures of Monosaccharides
- 24-7 Anomers of Monosaccharides: Mutarotation
- 24-8 Reactions of Monosaccharides: Side Reactions in Base
- 24-9 Reduction of Monosaccharides
- 24-10 Oxidation of Monosaccharides: Reducing Sugars
- 24-11 Nonreducing Sugars: Formation of Glycosides
- 24-12 Ether and Ester Formation
- 24-13 Reactions with Phenylhydrazine: Osazone Formation
- 24-14 Chain Shortening: The Ruff Degradation
- 24-15 Chain Lengthening: The KilianiFischer Synthesis
- 24-16 Fischers Proof of the Configuration of Glucose
- 24-17 Determination of Ring Size: Periodic Acid Cleavage of Sugars
- 24-18 Disaccharides
- 24-19 Polysaccharides
- 24-20 Nucleic Acids: Introduction
- 24-21 Ribonucleosides and Ribonucleotides
- 24-22 The Structure of Ribonucleic Acid
- 24-23 Deoxyribose and the Structure of Deoxyribonucleic Acid
- 24-24 Additional Functions of Nucleotides
- Summary in Chinese
- Study Problems
- Chapter 25 Amino Acids, Peptides, and Proteins
- 25-1 Introduction
- 25-2 Structure and Stereochemistry of the αAmino Acids
- 25-3 AcidBase 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 SolutionPhase Peptide Synthesis
- 25-11 SolidPhase Peptide Synthesis
- 25-12 Classification of Proteins
- 25-13 Levels of Protein Structure
- 25-14 Protein Denaturation
- Summary in Chinese
- Study Problems
- Chapter 26 Lipids
- 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
- Answers to Selected Problems
- Index
- Vocabulary
