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Question

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

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

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 SN1 reaction gives racemisation. Compound (iv) is a secondary carbocation so it undergoes racemisation by SN1 reaction mechanism.

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