Question:hard

Identify the major product formed in the following reaction sequence.

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Alkyl groups on benzene having benzylic hydrogen are oxidized by alkaline \(\mathrm{KMnO_4}\) to \(-\mathrm{COOH}\).
Updated On: Jun 15, 2026
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The Correct Option is D

Solution and Explanation

Step 1: Identify the first step on toluene.
Toluene reacts with acetyl chloride $CH_3COCl$ in the presence of anhydrous $AlCl_3$, which is a Friedel-Crafts acylation.
Step 2: Decide the position of attack.
The $-CH_3$ group is ortho and para directing, so the acetyl group adds mainly at the para position, giving para-methyl acetophenone, $p\text{-}CH_3C_6H_4COCH_3$.
Step 3: Oxidise with alkaline $KMnO_4$.
Hot alkaline $KMnO_4$ is a strong oxidant that converts benzylic side chains into $-COOH$ groups. Both the methyl side chain and the acetyl side chain are oxidised to carboxylic acid groups.
Step 4: Write the oxidised intermediate.
\[ p\text{-}CH_3C_6H_4COCH_3 \rightarrow p\text{-}HOOC\text{-}C_6H_4\text{-}COOH \] giving two $-COOH$ groups in the para arrangement.
Step 5: Acidify.
Dilute $H_2SO_4$ protonates the carboxylate salt to release the free dicarboxylic acid.
Step 6: Name the product.
The product is benzene-1,4-dicarboxylic acid, known as terephthalic acid, the answer marked option 4.
\[ \boxed{\text{Terephthalic acid}} \]
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