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
