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 BrnstedLowry 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 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 FirstOrder Nucleophilic Substitution: The SN1 Reaction
  7-13 Stereochemistry of the SN1Reaction
  7-14 Rearrangements in SN1 Reactions
  7-15 Comparison of SN1 and SN2 Reactions
  7-16 FirstOrder Elimination: The E1 Reaction
  7-17 Positional Orientation of Elimination: Zaitsevs 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 SN2 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 Hückels Rule
  17-6 Molecular Orbital Derivation of Hückels 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
  2313 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 Fischers 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