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Chapter 15 Outline

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  • 1. Electrophilic Aromatic Substitution

    Electrophilic Aromatic Substitution reactions

    Synthesis of Benzene derivatives

    Introduction to Electrophilic Aromatic Substitution

    1.1 Halogenation of Benzene

    Halogenation of Benzene

    Halogenation of Benzene (2)

    1.2 Nitration of Benzene

    Nitration of Benzene

    Nitration of Benzene (2)

    Nitration and Sulfonation of Benzene

    1.3 Sulfonation of Benzene

    Nitration and Sulfonation of Benzene

    The Sulfonation of Benzene

    2. Friedel-Crafts Reactions

    2.1 Friedel-Crafts Alkylation

    The Friedel-Crafts Alkylation of Benzene

    2.2 Friedel-Crafts Acylation

    Using Acyl Chlorides in Friedel-Crafts Reactions

    The Friedel-Crafts Acylation of Benzene

    3. Substitution effects on orientation

    Directing Effects

    3.1 Theory of Directing effects

    Substitution Reactions of Benzene Derivatives (II)

    AR4. Activation and Deactivation

    Inductive Effects of Alkyl Groups

    3.2 Activating, Ortho, Para-Directing Substituents

    Activating Group

    Modifying the Influence of Strong Activating Groups

    3.3 Deactiving, Meta-Directors

    3.4 Halogen Substituents: Deactivating, but Ortho- Para-Directing

    3.5 Multiple Substituents

    4. Nucleophilic Aromatic Substitution

    4.1 Benzyne Intermediates

    5. Birch Reduction of Aromatic Molecules

    5.1 Regioselectivity of Birch Reduction

    6. Side-Chain Reactions of Benzene Derivatives

    Phenylmethyl or Benzylic Halides

    6.1 Oxidation

    Oxidation of Organic Molecules by KMnO4

    6.2 Allylic and Benzylic Halogenation

    6.3 Substitution (SN¬1 and SN2)

    6.4 Hydrogenolysis

    7. Phenols

    7.1 Acidity of Phenols

    7.2 Oxidation

    7.3 Electrophilic Substitution of the Phenol Aromatic Ring

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