(Solved): Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. Th ...

Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic \( \mathrm{H}^{+} \)adds to the sp. corbon with the most hydrogens to vield the most stable corbocotion intermediote, which then adds water to give the product alcohol. Because a carbocation intermediate is formed, rearrangements con occur prior to the addition of water. To avoid the possibility of rearrangement and still give a Markovmikov alcohol, alkenes can instead be treativo with mercury(II) acetate in aqueous THF and then subsequently reduced with sodium borohydrife. This reaction. proceeds through o cyclic mercurinium ton intermediate which cannot rearrange. Water adds to the cyctic intermediate at the most substituted carbon to give an organomercury olcohol, 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. \( \mathrm{H}_{2} \ddot{\mathrm{O}} \longrightarrow \)