Chapter 1 Introduction and Renew1-1 The Origins of Organic Chemistry1-2 Principles of Atomic Structure1-3 Bond Formation:The Octet Rule1-4 Lewis Structures1-5 Multiple Bonding1-6 Electronegativity and Bond Polarity1-7 Formal Charges1-8 Ionic Structures1-9 Resonance1-10 Structural Formulas1-11 Molecular Formulas and Empirical Formulas1-12 Arrhenius Acids and Bases1-13 Brensted.Lowry Acids and Bases1-14 Lewis Acids and BasesSummary in ChineseStudy ProblemsChapter 2 Structure and Properties of Organic Molecules2-1 Wave Properties of Electrons in Qrbitals2-2 Molecular Orbitals2-3 Pi Bonding2-4 Hybridization and Molecular Shapes2-5 Drawing Three-Dimensional Molecules2-6 General Rules of Hybridization and Geometry2-7 Bond Rotatio2-8 Isomerism2-9 Polarity of Bonds and Molecules2-10 Intermolecular Forces2-11 Polarity Effects on SolubilitiesSummary in ChineseStudy ProblemsChapter 3 Brief Introduction and Nomenclature of Organic Compounds3-1 Hydrocarbons3-2 Organic Compounds Containing Oxyge3-3 Organic Compounds Containing Nitroge3-4 Nomenclature of A1kanes3-5 Nomenclature of Alkenes3-6 Nomenclature of Alkynes3-7 Nomenclature of Cycloalkanes3-8 Nomenclature of Benzene Derivatives3-9 Nomenclature of Alkyl Halides3-10 Nomenclature of Alcohols and Thiols3-11 Nomenclature of Ethers and Sulfides3-12 Nomenclature of Amines3-13 Nomenclature of Ketones and Aldehydes3-14 Nomenclature of Carboxylic Acids3-15 Structure and Nomenclature of Acid DerivativesSummary in ChineseStudy ProblemsChapter 4 Structure and Stereochemistry of Alkanes4-1 Physical Properties of Alkanes4-2 Uses and Sources of Alkanes4-3 Reactions of Alkanes4-4 Structure and Conformations of Alkanes4-5 Cycloalkanes4-6 Cyclohexane Conformations4-7 Conformations of Monosubstituted Cyclohexanes4-8 Conformations of Disubstituted CyclohexanesSummary in ChineseStudy ProblemsChapter 5 The Study of Chemical Reactions5-1 Introductio5-2 Chlorination of Methane5-3 The Free-Radical Chain Reactio5-4 Equilibrium Constants and Free Energy5-5 Enthalpy and Entropy5-6 Bond-Dissociation Enthalpies5-7 Enthalpy Changes in Chlorinatio5-8 Kinetics and the Rate Equatio5-9 Activation Energy and the Temperature Dependence of Rates5-10 Transition States5-11 Rates of Multistep Reactions5-12 Temperature Dependence of Halogenatio5-13 Selectivity in Halogenatio5-14 The Hammond Postulate5-15 Radical Inhibitors5-16 Reactive IntermediatesSummary tin ChineseStudy ProblemsChapter 6 Stereochemistry6-1 Introductio6-2 Chirality6-3(R)and(S)Nomenclature of Asymmetric Carbon Atoms6-4 Optical Activity6-5 Racemic Mixtures6-6 Enantiomeric Excess and Optical Purity6-7 Chirality of Conformationally Mobile Systems6-8 Chiral Compounds without Asymmetric Atoms6-9 Fischer Projections6-10 Diastereomers6-11 Stereochemistry of Molecules with Two or More Asymmetric Carbons6-12 Meso Compounds6-1 3 Absolute and Relative Configuratio6-14 Physical Properties of Diastereomers6-1 5 Resolution of EnantiomersSummary in ChineseStudy ProblemsChapter 7 Alkyl Halides:Nucleophilic Substitution and Eliminatio7-1 Introductio7-2 Common Uses of Alkyl Halides7-3 Structure of Alkyl Halides7-4 Physical Properties of Alkyl Halides1-5 Preparation of Alkyl Halides7-6 Reactions of Alkyl Halides:Substitution and Eliminatio7-7 Second-Order Nucleophilic Substitution:The SN2 Reactio7-8 Generality of the SN2 Reactio7-9 Factors Affecting SN2 Reactions: Strength of the Nucleophile7-10 Reactivity of the Substrate in SN2 Reactions7-11 Stereochemistry of the SN2 Reactio7-12 First.Order Nucleophilic Substitution:The SNl Reactio7-13 Stereochemistry of the SNl Reactio7-14 Rearrangements in SN 1 Reactions7-15 Comparison of SNl and SN2 Reactions7-16 First.Order Elimination:The E1 Reactio7-17 Positional Orientation of Elimination:Zaitsevs Rule7-18 Second-Order Elimination:The E2 Reactio7-19 Stereochemistry of the E2 Reactio7-20 Comparison of E1 and E2 Elimination MechanismsSummary in ChineseStudy ProblemsChapter 8 Structure and Synthesis of Alkenes8-1 Introductio8-2 The 0rbital Description of the Alkene Double Bond8-3 Elements of Unsaturatio8-4 Commercial Importance of Alkenes8-5 Stability of Alkenes8-6 Physical Properties of Alkenes8-7 Alkene Synthesiy Elimination of Alkyl Halides8-8 Alkene Synthesiy Dehydration of Alcohols8-9 Alkene Synthesiy High-Temperature Industrial MethodsSummary in ChineseStudy ProblemsChapter 9 Reactions of Aikenes9-1 Reactivity of the Carbon-Carbon Double Bond9-2 Electrophilic Addition to Alkenes9-3 Addition of Hydrogen Halides to Alkenes9-4 Addition of Water:Hydration of Alkenes9-5 Hydration by Oxymercuration-Demercuratio9-6 Alkoxymercuration-Demercuratio9-7 Hydroboration of Alkenes9-8 Addition of Halogens to Alkenes9-9 Formation of Halohydrins9-10 Catalytic Hydrogenation of Alkenes9-11 Addition of Carbenes to Alkenes9-12 Epodation of Alkenes9-13 Acid-Catalyzed Opening of Epodes9-14 Syn Hydroxylation of Alkenes9-15 Odative Cleavage of Alkenes9-16 Polymerization of AlkenesSummary in ChineseStudy ProblemsChapter 10 Alkynes10-1 Introductio10-2 Physical Properties of Alkynes10-3 Commercial Importance of Alkynes10-4 Electronic Structure of Alkynes10-5 Acidity of Alkynes:Formation of Acetylide Ions10-6 Synthesis of Alkynes from Acetylides10-7 Synthesis of Alkyney Elimination Reactions10-8 Addition Reactions of Alkynes10-9 Odation of AlkynesSummary in ChineseStudy ProblemsChapter 11 Conjugated Systems and Orbital Symmetry11-1 Introductio11-2 Stabilities of Dienes11-3 Molecular Orbitals of a Conjugated System11-4 Allylic Cations11-5 1,2-and 1,4-Addition to Conjugated Dienes11-6 Kinetic versus Thermodynamic Control in the Addition of HBr to 1.3-Butadiene11-7 Allylic Radicals11-8 Molecular Orbitals of the Allylic System11-9 Electronic Configurations of the Allyl Radical,Cation,and Anio11-10 SN2 Displacement Reactions of Allylic Halides and Tosylates11-11 The Diels-Alder Reactio1-12 The Diels-Alder as an Example of a Pericyclic ReactioSummary in ChineseStudy ProblemsChapter 12 Infrared and Ultraviolet Spectros-copy12-1 Introductio12-2 The Electromagnetic Spectrum12-3 The Infrared Regio12-4 Molecular Vibrations12-5 IR-Active and IR.Inactive Vibrations12-6 Measurement of the IR Spectrum12-7 Infrared Spectroscopy of Hydrocarbons12-8 Characteristic Absorptions of Alcohols and Amines12-9 Characteristic Absorptions of Carbonyl Compounds12-10 Characteristic Absorptions of Bonds12-11 Simplified Summary of IR Stretching Frequencies12-12 Reading and Interpreting IR Spectra12-13 Uhraviolet Absorption Spectroscopy12-1 4 Ultraviolet Light and Electronic Transitio12-15 Measurement of the UV-Visible Spectrum12-16 Interpreting UV-Visible SpectraSummary in ChineseStudy ProblemsChapter 13 Nuclear Magnetic Resonance Spectroscopy and Mass Spectrometry13-1 Introduction to Nuclear Magnetic Resonance Spectroscopy13-2 Theory of Nuclear Magnetic Resonance13-3 Magnetic Shielding by Electrons13-4 The NMR Spectrometer13-5 The Chemical Shift13-6 The Number of Signals13-7 Areas of the Peaks13-8 Spin-Spin Splitting13-9 Carbon-13 NMR Spectroscopy13-10 Interpreting Carbon NMR Spectra13-11 Introduction to Mass Spectrometry13-12 Determination of the Moleeular Formula by Mass Spectrometry13-13 Fragmentation Patterns in Mass SpectrometrySummary in ChineseStudy ProblemsChapter 14 Structure and Synthesis of Alcohols14-1 Introductio14-2 Structure and Classification of Alcohols14-3 Physical Properties of Alcohols14-4 Commercially Important Alcohols14-5 Acidity of Alcohols and Phenols14-6 Organometallic Reagents for Alcohol Synthesis14-7 Synthesis of Alcohols:Addition of Organometallic Reagents to Carbonyl Compounds14-8 Side Reactions of Organometallic Reagents:Reduction of Alkyl Halides14-9 Synthesis of 1°and 2°Alcohols: Reduction of the Carbonyl Group14-10 Thiols(Mercaptans)Summary in ChineseStudy ProblemsChapter 15 Reactions of Alcohols15-1 Odation States of Alcohols and Related Functional Groups15-2 Odation of Alcohols15-3 Additional Methods for Odizing Alcohols15-4 Alcohols as Nucleophiles and Electro-philes:Formation of Tosylates15-5 Reduction of Alcohols15-6 Reactions of Alcohols with Hydrohalic Acids15-7 Reactions of Alcohols with Phosphorus Halides15-8 Reactions of Alcohols with Thionyl Chloride15-9 Dehydration Reactions of Alcohols15-10 Unique Reactions of Diols15-11 Esterification of Alcohols15-12 Reactions of AlkodesSummary in ChineseStudy ProblemsChapter 16 Ethers, Epoxdes,and SulfdesChapter 17 Aromatic CompiundsChapter 18 Eeactions of Aromatic CompoundsChapter 19 Ketones and AldehydesChapter 20 AminesChapter 21 Carboxylic AcidsChapter 22 Carboxylic Acid DerivativesChapter 23 Condensations and Alpha Substitutions of Carbonyl CompoundsChapter 24 Carbohydrates and Nucleic AcidsChapter 25 Amino Acids, Peptides, and ProteinsChapter 26 LipidsAnswers to Selected ProblemsIndexVocabulary 作
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