Chemistry - Hydrocarbon Question with Solution | TestHub

An alkene reacts with diborane/THF to produce an alkyl borane. Oxidation and hydrolysis of the alkyl borane with hydrogen peroxide and base yield alcohol.

Hydroboration

$\mathrm{R}=2-$methylcyclopentyl

Oxidation

In the first step, boron and hydrogen undergo syn addition to the alkene; in the second step, treatment with hydrogen peroxide and base replaces the boron with $-\mathrm{OH}$ with retention of configuration. The net addition of $-\mathrm{H}$ and $-\mathrm{OH}$ occurs with anti-Markovnikov regioselectivity and syn stereoselectivity.