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Which of the following compounds will undergo racemisation when solution of KOH hydrolyses?

1. (i) CH2Cl
2. (ii) CH3CH2CH2Cl
3. (iii) H3C–CH–CH2Cl
4. (iv) CH3 \n | \n CH \n | \n Cl \n | \n C2H5

Correct answer: (iv) CH3 \n | \n CH \n | \n Cl \n | \n C2H5

Solution

Racemisation occurs when a compound has a chiral center and undergoes a reaction that leads to the formation of both enantiomers. Option (iv) has a chiral carbon (attached to CH3, Cl, H, and C2H5), making it capable of racemisation during hydrolysis.

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