12.6 Substitution Reactions of Alcohols

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    Reaction with H-X (HI, HBr or HCl/ZnCl2)

    -SN1 for 3° and 2° alcohols; SN2 for 1° alcohols

    hbr reaction with alcohol
    hbr reaction with alcohol 2

    Reaction with PBr3 (for 1° and 2° alcohols)

    pbr3 reaction with alcohol
    pyridine

    Reaction with SOCl2 (for 1° and 2° alcohols)

    socl2 reaction with alcohol

    Conversion to Sulfonate Esters

    tscl pyridine
    tosylate ester