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2: Properties and Reactions of Alkanes

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    Chapter 3: Reactions of Alkanes

    Strength of Alkane Bonds and Radicals
    Structure of Alkyl Radicals and Hyperconjugation
    Chlorination of Methane and the Radical Chain Mechanism
    Other Radical Halogenations of Methane
    Chlorination of Higher Alkanes
    Selectivity in Radical Halogenation with Fluorine and Bromine
    Synthetic Radical Halogenation
    Combustion and the Relative Stabilities of Alkanes

    Chapter 4: Cycloalkanes

    Naming Cycloalkanes
    Physical Properties of Cycloalkanes
    Ring Strain and the Structure of Cycloalkanes
    Substituted Cyclohexanes
    Larger Cycloalkanes
    Polycyclic Alkanes

    Chapter 6: Properties and Reactions of Haloalkanes

    Physical Properties of Haloalkanes
    Nucleophilic Substitution
    Using Electron-Pushing Arrows
    Kinetics of Nucleophilic Substitution Reactions
    SN2 Reactions-The Leaving Group
    SN2 Reactions-The Nucleophile
    SN2 Reactions-The Substrate

    Solvolysis of Secondary and Tertiary Haloalkanes
    Unimolecular Nucleophilic Substitution
    Stereochemical Consequences of SN1 Reactions
    Effects of Solvent, Leaving Group, and Nucleophile on Unimolecular Substitution
    Effect of the Alkyl Group on the SN1 Reaction-Carbocation Stability
    Unimolecular Elimination-E1
    Unimolecular Elimination-E2
    Competition Between Substitution and Elimination-Structure Determines Function

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