Question

The compound which does not lead to benzoic acid by oxidation with $KMnO_4$ is

• A. Toluene
• B. benzyl alcohol
• C. n-butylbenzene
• D. t-butylbenzene

Answer 1

Answer: (D)

t-butylbenzene

Answer 2

The compound which does not lead to benzoic acid by oxidation with $KMnO _{4}$ is $t$ -butylbenzene. In this compound, the side chain has no $C - H$ bond at $\alpha$ -carbon (with respect to benzene nucleus) Hence, benzene ring get cleaved.

Toluene, benzyl alcohol, $n$ -butyl benzene and styrene all contain one benzylic $C - H$ bond and on oxidation forms benzoic acid.