9.7 Hydration of Alkynes

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    Acid-Catalyzed Hydration of Alkynes

    Less Substituted More Substituted
    Two Groups Added
    H
    OH
    Reagents H2SO4 (i.e. H3O+)
    Regioselectivity Markovnikov
    Stereospecificity None
    Other Characteristics The intermediate is an enol which tautomerizes to a ketone.
    Terminal alkynes require Hg2+ as a catalyst.
    acid catalyzed hydration of alkynes 01
    acid catalyzed hydration of alkynes 02

    Hydroboration-Oxidation of Alkynes

    Less Substituted More Substituted
    Two Groups Added
    OH
    H
    Reagents 1. Sia2BH.THF     or     1. R2BH
    2. H2O2, NaOH    or     2. H2O2, NaOH
    Regioselectivity Anti-Markovnikov
    Stereospecificity Syn
    Other Characteristics Often use “bulky” boranes instead of BH3
    bulky boranes
    hydroboration oxidation of alkynes 01
    hydroboration oxidation of alkynes 02