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  • Mechanism of Hydroboration

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    Kasturi Samant
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    1. Hydroboration adds BH3 to an alkene in an anti-Markovnikov fashion, adding the BH group to the less substituted carbon. 2. Oxidation replaces the B with an OH group, using either H2O2/NaOH or a peroxide reacting with the trialkylborane. This produces the alcohol product in an anti-Markovnikov manner.

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    1. Hydroboration adds BH3 to an alkene in an anti-Markovnikov fashion, adding the BH group to the less substituted carbon. 2. Oxidation replaces the B with an OH group, using either H2O2/NaOH or a peroxide reacting with the trialkylborane. This produces the alcohol product in an anti-Markovnikov manner.

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    10 views1 page

    Mechanism of Hydroboration

    Uploaded by

    Kasturi Samant
    1. Hydroboration adds BH3 to an alkene in an anti-Markovnikov fashion, adding the BH group to the less substituted carbon. 2. Oxidation replaces the B with an OH group, using either H2O2/NaOH or a peroxide reacting with the trialkylborane. This produces the alcohol product in an anti-Markovnikov manner.

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    Mechanism of Hydroboration-Oxidation 1. Hydroboration: BH3 adds to alkene Anti-Markovnikov 3 C C + BH3 C C H B(alkyl)2 2. Oxidation: Replacement of B by OH.

    You do not need to memorize this mechanism. Just be able to predict the overall product as done in class. a) H2O2 & NaOH react. H O O H + OHH O O + H2O

    b) H-O-O - reacts with Trialkylborane


    C C H B(alkyl)2 H O O C C H B(alkyl)2 O H O migration of alkyl group to oxygen H O O and alkyl migration two more times C C H O B(alkyl)2 + OH-

    alcohol product C C H O H + B(Oalkyl)2 OH OH+ C C H O B(Oalkyl)2 OH H O H

    C C H O B(Oalkyl)2 OH-

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