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