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(D) Alkaline $KMnO_4$ is a strong oxidizing agent that oxidizes alkyl side chains attached to a benzene ring to a carboxylic acid group $(-COOH)$,prov

Vedclass · Accepted Answer

$t-$Butyl benzene

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(D) Alkaline $KMnO_4$ is a strong oxidizing agent that oxidizes alkyl side chains attached to a benzene ring to a carboxylic acid group $(-COOH)$,provided that the benzylic carbon has at least one hydrogen atom.$1$. $n-$Propyl benzene $(C_6H_5-CH_2-CH_2-CH_3)$ has two hydrogens on the benzylic carbon,so it oxidizes to benzoic acid.$2$. Styrene $(C_6H_5-CH=CH_2)$ has a benzylic hydrogen,so it oxidizes to benzoic acid.$3$. Acetophenone $(C_6H_5-CO-CH_3)$ contains a carbonyl group at the benzylic position,but the oxidation of the methyl group attached to the carbonyl can lead to benzoic acid under vigorous conditions.$4$. $t-$Butyl benzene $(C_6H_5-C(CH_3)_3)$ has no hydrogen atom on the benzylic carbon. Therefore,it is resistant to oxidation by alkaline $KMnO_4$ and does not yield benzoic acid.

Which one of the following compounds does not give benzoic acid when treated with alkaline $KMnO_4$?

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