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Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry

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Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H+ adds to the sp^2 carbon with the most hydrogens to yield the most stable carbocation intermediate, which then adds water to give the product alcohol.



 To avoid the possibility of rearrangement and still give a Markovnikov alcohol, alkenes can instead be treated with mercury(II) acetate in aqucous THF and then subsequently reduced with sodium borohydride. This reaction proceeds through a cyclic mercurinium ion intermediate which cannot rearrange. Water adds to the cyclic intermediate at the most substituted carbon to give an organomercury alcohol. The reduction step with sodium borohydride is complex and involves radicals.

 Draw curved arrows to show the movement of electrons in this step of the mechanism.

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