18.2 Friedel Crafts Alkylation and Acylation

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    Friedel-Crafts Alkylation

    EAS Reaction / Reagents Electrophile Name
    Friedel-Crafts Alkylation
    Characteristics of Friedel-Crafts Alkylations
    -Fails with moderately and strongly deactivated benzenes (still works with a halogenated benzene)
    -Carbocation rearrangements are possible
    -Alkylation activates the ring: multiple alkylations are hard to avoid
    EAS Reaction / Reagents Electrophile Name
    Friedel-Crafts Acylation

    Friedel-Crafts Acylation

    Characteristics of Friedel-Crafts Acylations
    -Fails with moderately and strongly deactivated benzenes (still works with a halogenated benzene)
    -Carbocation rearrangements don’t occur
    -Generally occurs only once
    -Favors para if ortho/para director is on benzene due to bulkiness
    -Formylation (Gattermann-Koch Synthesis) is a special case