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    Alkenes do not undergo hydration upon treatment with water even at very high temperatures. There are two approaches to hydrating alkenes:

    1. Reaction of the alkene with water in the presence of a strong-acid catalyst.
    2. Using an indirect method

    Hydroboration-oxidation, sometimes casually called hydroboration for convenience, is a common indirect method used to hydrate alkenes.


    net reaction:


    The protocol is carried out in two stages:

    Stage 1: Hydroboration

    The alkene is treated with a source of borane ( diborane or borane-THF complex), which converts the alkene into a trialkylborane.

    Stage 2: Oxidation

    The trialkylborane is treated with H2O2 and a strong base, usually NaOH, in aqueous medium, which converts the trialkylborane into an alcohol.

    Stage 1:


    This reaction is an anti-Markovnikov addition and a syn addition.

    Stage 2:


    Stage 1 + Stage 2 =


    The net reaction is an anti-Markovnikov addition:


    see also oxymercuration-reduction

    This page titled Hydroboration-Oxidation is shared under a All Rights Reserved (used with permission) license and was authored, remixed, and/or curated by Gamini Gunawardena via source content that was edited to the style and standards of the LibreTexts platform; a detailed edit history is available upon request.

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