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Chapter 1Introduction1. 1The Shape of Molecules1. 2Atomic and Molecular Orbitals1.3Structure & Bonding1.4Chemical Bonding and Valence1.5Covalent Bonding1.6Valence1.7Charge Distribution1.8Functional GroupsChapter 2Alkanes2.1Alkane Nomenclature2.1.1IUPAC Rules for Alkane Nomenclature2. 2Conformational Stereoisomers2.2.1Ethane Conformations2.2.2Butane Conformations2. 3Physical Properties of Alkanes2.4Chemical Properties of AlkanesChapter 3Alkenes3.1Alkene and Cycloalkene Nomenclature3.1.1IUPAC Rules3.1.2Stereoisomers3.1.3Configurational Stereoisomers of Alkenes3.1.4Nomenclature of Alkene Stereoisomers3.1.5The Sequence Rule for Assignment of Alkene Configurations3.2Physical Properties of Alkenes3.3Reactions of Alkenes3.3.1Addition Reactions of Alkenesa. Addition of Strong Bronsted Acidsb. Regioselectivity and the Markovnikov Rulec. Rearrangement of Carbocationsd. Addition of lewis Acids £¨Electrophilic Reagents£©e. Stereoselectivity in Addition Reactions to Double Bondsf. Bronsted Acid Additionsg. Addition Reactions Initiated by Electrophilic Halogenh. Addition Reactions Involving Other Cyclic Onium Intermediates3.3.2Hydrogenation3.3.3Oxidations£¨i£© Hydroxylation£¨ii£© Epoxidation£¨iii£© Oxidative Cleavage of Double Bonds3.3.4Free Radical Reactions of Alkenesa. Addition of Radicals to Alkenesb. Allylic SubstitutionChapter 4Alkynes4.1IUPAC Rules for Alkyne Nomenclature4.2Reactions of Alkynes4.2.1Addition Reactions of Alkynesa. Catalytic Hydrogenationb. Addition by Electrophilie Reagentsc. Hydration of Alkynes and Tautomerismd. Hydroboration Reactionse. Oxidations4.2.2Nucleophilic Addition Reactions & Reduction4.2.3Acidity of Terminal Alkynes4.3Physical Properties of AlkynesChapter 5Dienes5.1Properties of Dienes5.1.1Addition Reactions of Dienes5.1.2Diels-Alder Cycloaddition5.1.3Stereospecificity5.2Properties of Cumulated Dienes5.2.1Addition Reactions of MlenesChapter 6Cyeloalkanes6.1IUPAC Rules for Cycloalkane Nomenclature6.2Ring Conformations6.2.1Substituted Cyclohexane Compounds6.2.2Conformational Structures of Disubstituted Cyclohexanes6.2.3Configurational Stereoisomers of Cycloalkanes6.3Cycloalkanes reactionsChapter 7Alkyl Halide7.1Naming7.2Alkyl Halide Reactions7.3Mechanisms of Nucleophilic Substitution Reactions7.3.1The SN2 Mechanism7.3.2The SN1 Mechanism7.3.3Activation by Electrophilic Cations7.3.4The E2 Reaction7.3.5Stereochemistry of the E2 Reaction.3.6The E1 Reaction7.3.7Summary of Factors Influencing Alkyl Halide Reactions7.4Organometallic Compounds7.4.1Reactions of Alkyl Halides with Reducing Metals7.5Reactions of Dihalides7.5.1Preparation of Alkynes by DehydrohalogenationChapter 8Aromatic compounds8.1Benzene Derivatives8.2Aromaticity8.3Aromatic Substitution Reactions8.3.1Substitution Reactions of Benzene and Other Aromatic Compounds8.3.2A Mechanism for Electrophilic Substitution Reactions of Benzene8.3.3Substitution Reactions of Benzene Derivatives8.3.4Characteristics of Specific Substitution Reactions8.3.5Electrophilic Substitution of Disubstituted Benzene Rings8.4Reactions of Substituent Groups8.5Reactions of Fused Benzene Rings¡­¡­ Chapter 9 Alcohol Phenol and EthersChapter 10 Aldehydes and KetonesChapter 11 Carboxylic AcidsChapter 12 Derivatives of Carboxylic AcidsChapter 13 Chemistry of Amines