Chapter 1 Introduction and Renew 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 Brensted．Lowry 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 in Qrbitals 2-2 Molecular Orbitals 2-3 Pi Bonding 2-4 Hybridization and Molecular Shapes 2-5 Drawing Three-Dimensional Molecules 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 A1kanes 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 Chemical Reactions 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 The Hammond Postulate 5-15 Radical Inhibitors 5-16 Reactive Intermediates Summary tin 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 Asymmetric Carbons 6-12 Meso Compounds 6-1 3 Absolute and Relative Configuration 6-14 Physical Properties of Diastereomers 6-1 5 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 Alkyl Halides 1-5 Preparation of Alkyl Halides 7-6 Reactions of Alkyl Halides：Substitution and Elimination 7-7 Second-Order 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 First．Order Nucleophilic Substitution：The SNl Reaction 7-13 Stereochemistry of the SNl Reaction 7-14 Rearrangements in SN 1 Reactions 7-15 Comparison of SNl and SN2 Reactions 7-16 First．Order Elimination：The E1 Reaction 7-17 Positional Orientation of Elimination：Zaitsevs Rule 7-18 Second-Order Elimination：The E2 Reaction 7-19 Stereochemistry of the E2 Reaction 7-20 Comparison of E1 and E2 Elimination Mechanisms Summary in Chinese Study Problems Chapter 8 Structure and Synthesis of Alkenes 8-1 Introduction 8-2 The 0rbital 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 High-Temperature Industrial Methods Summary in Chinese Study Problems Chapter 9 Reactions of Aikenes 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 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 Orbital Symmetry 11-1 Introduction 11-2 Stabilities of Dienes 11-3 Molecular Orbitals of a Conjugated System 11-4 Allylic Cations 11-5 1，2-and 1，4-Addition to Conjugated Dienes 11-6 Kinetic versus Thermodynamic Control in the Addition of HBr to 1．3-Butadiene 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 Diels-Alder Reaction 1-12 The Diels-Alder as an Example of a Pericyclic Reaction Summary in Chinese Study Problems Chapter 12 Infrared and Ultraviolet Spectros-copy 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 Uhraviolet Absorption Spectroscopy 12-1 4 Ultraviolet Light and Electronic Transition 12-15 Measurement of the UV-Visible Spectrum 12-16 Interpreting UV-Visible Spectra Summary in Chinese Study Problems Chapter 13 Nuclear Magnetic Resonance Spectroscopy and Mass Spectrometry 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 Moleeular 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, Epoxdes,and Sulfdes Chapter 17 Aromatic Compiunds Chapter 18 Eeactions of Aromatic Compounds Chapter 19 Ketones and Aldehydes Chapter 20 Amines Chapter 21 Carboxylic Acids Chapter 22 Carboxylic Acid Derivatives Chapter 23 Condensations and Alpha Substitutions of Carbonyl Compounds Chapter 24 Carbohydrates and Nucleic Acids Chapter 25 Amino Acids, Peptides, and Proteins Chapter 26 Lipids Answers to Selected Problems Index Vocabulary
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