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Question 47 of 66

Q.Propene on oxidation with diborane in presence of alkaline hydrogen peroxide gives —

(a) propan-1-ol
(b) propan-2-ol
(c) allyl alcohol
(d) propan-1, 2-diol
Maharashtra MsbshseMaharashtra HSC (MSBSHSE) Board 2018MCQ· 1mImportance★★★★★
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Hydroboration–oxidation adds −OH-OH to the LESS substituted (terminal) carbon, giving the anti-Markovnikov, primary alcohol product.

Hydroboration of propene (CH3−CH=CH2CH_3-CH=CH_2) with diborane (B2H6B_2H_6) proceeds with boron attaching to the less hindered, terminal carbon (anti-Markovnikov regiochemistry), forming a trialkylborane. Subsequent oxidation with alkaline hydrogen peroxide replaces the C–B bond with a C–OH bond with retention of position, giving the primary alcohol:

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