Chapter 1Introduction 1. 1The Shape of Molecules 1. 2Atomic and Molecular Orbitals 1.3Structure & Bonding 1.4Chemical Bonding and Valence 1.5Covalent Bonding 1.6Valence 1.7Charge Distribution 1.8Functional Groups Chapter 2Alkanes 2.1Alkane Nomenclature 2.1.1IUPAC Rules for Alkane Nomenclature 2. 2Conformational Stereoisomers 2.2.1Ethane Conformations 2.2.2Butane Conformations 2. 3Physical Properties of Alkanes 2.4Chemical Properties of Alkanes Chapter 3Alkenes 3.1Alkene and Cycloalkene Nomenclature 3.1.1IUPAC Rules 3.1.2Stereoisomers 3.1.3Configurational Stereoisomers of Alkenes 3.1.4Nomenclature of Alkene Stereoisomers 3.1.5The Sequence Rule for Assignment of Alkene Configurations 3.2Physical Properties of Alkenes 3.3Reactions of Alkenes 3.3.1Addition Reactions of Alkenes a. Addition of Strong Bronsted Acids b. Regioselectivity and the Markovnikov Rule c. Rearrangement of Carbocations d. Addition of lewis Acids （Electrophilic Reagents） e. Stereoselectivity in Addition Reactions to Double Bonds f. Bronsted Acid Additions g. Addition Reactions Initiated by Electrophilic Halogen h. Addition Reactions Involving Other Cyclic Onium Intermediates 3.3.2Hydrogenation 3.3.3Oxidations （i） Hydroxylation （ii） Epoxidation （iii） Oxidative Cleavage of Double Bonds 3.3.4Free Radical Reactions of Alkenes a. Addition of Radicals to Alkenes b. Allylic Substitution Chapter 4Alkynes 4.1IUPAC Rules for Alkyne Nomenclature 4.2Reactions of Alkynes 4.2.1Addition Reactions of Alkynes a. Catalytic Hydrogenation b. Addition by Electrophilie Reagents c. Hydration of Alkynes and Tautomerism d. Hydroboration Reactions e. Oxidations 4.2.2Nucleophilic Addition Reactions & Reduction 4.2.3Acidity of Terminal Alkynes 4.3Physical Properties of Alkynes Chapter 5Dienes 5.1Properties of Dienes 5.1.1Addition Reactions of Dienes 5.1.2Diels-Alder Cycloaddition 5.1.3Stereospecificity 5.2Properties of Cumulated Dienes 5.2.1Addition Reactions of Mlenes Chapter 6Cyeloalkanes 6.1IUPAC Rules for Cycloalkane Nomenclature 6.2Ring Conformations 6.2.1Substituted Cyclohexane Compounds 6.2.2Conformational Structures of Disubstituted Cyclohexanes 6.2.3Configurational Stereoisomers of Cycloalkanes 6.3Cycloalkanes reactions Chapter 7Alkyl Halide 7.1Naming 7.2Alkyl Halide Reactions 7.3Mechanisms of Nucleophilic Substitution Reactions 7.3.1The SN2 Mechanism 7.3.2The SN1 Mechanism 7.3.3Activation by Electrophilic Cations 7.3.4The E2 Reaction 7.3.5Stereochemistry of the E2 Reaction .3.6The E1 Reaction 7.3.7Summary of Factors Influencing Alkyl Halide Reactions 7.4Organometallic Compounds 7.4.1Reactions of Alkyl Halides with Reducing Metals 7.5Reactions of Dihalides 7.5.1Preparation of Alkynes by Dehydrohalogenation Chapter 8Aromatic compounds 8.1Benzene Derivatives 8.2Aromaticity 8.3Aromatic Substitution Reactions 8.3.1Substitution Reactions of Benzene and Other Aromatic Compounds 8.3.2A Mechanism for Electrophilic Substitution Reactions of Benzene 8.3.3Substitution Reactions of Benzene Derivatives 8.3.4Characteristics of Specific Substitution Reactions 8.3.5Electrophilic Substitution of Disubstituted Benzene Rings 8.4Reactions of Substituent Groups 8.5Reactions of Fused Benzene Rings …… Chapter 9 Alcohol Phenol and Ethers Chapter 10 Aldehydes and Ketones Chapter 11 Carboxylic Acids Chapter 12 Derivatives of Carboxylic Acids Chapter 13 Chemistry of Amines
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