Question

The compound which does not lead to benzoic acid by oxidation with $KMn{O}_4$ is

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

Answer 1

Answer: (D)

The compound which does not lead to benzoic acid by oxidation with $KMn{O}_4$ 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.