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  4. The compound which does not lead to benzoic acid by oxidation with KMnO4 is

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

KEAMKEAM 2019Aldehydes Ketones and Carboxylic Acids

Solution:

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.

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