Question

Which of the following compounds will undergo racemisation when solution of KOH hydrolyses?
(i)
(ii)
(iii)
(iv)

• A. Only (iv)
• B. (i) and (ii)
• C. (ii) and (iv)
• D. (iii) and (iv)

Answer 1

The correct option is A Only (iv)

Only (iv) option will undergo racemisation when the solution of KOH hydrolyses because it is the only compound which contains a chiral carbon atom.

Substrate which undergoes $S_{N}1$ reaction gives racemisation. Compound (iv) is a secondary carbocation so it undergoes racemisation by $S_{N}1$ reaction mechanism.