Question:
Identify the major product formed in the following reaction sequence.
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 reaction.
Toluene reacts with acetyl chloride \(\mathrm{CH_3COCl}\) in the presence of anhydrous \(\mathrm{AlCl_3}\).
This is Friedel-Crafts acylation.
Since \(-\mathrm{CH_3}\) group is ortho-para directing, the major product is para-methyl acetophenone.
\[ \mathrm{C_6H_5CH_3 \rightarrow p\text{-}CH_3C_6H_4COCH_3} \]
Step 2: Oxidation with alkaline \(\mathrm{KMnO_4}\).
Strong oxidizing agent \(\mathrm{KMnO_4/KOH}\) oxidizes benzylic side chains to carboxylic acid groups.
Thus, both side chains are converted into \(-\mathrm{COOH}\) groups.
\[ p\text{-}\mathrm{CH_3C_6H_4COCH_3} \rightarrow p\text{-}\mathrm{HOOC-C_6H_4-COOH} \]
Step 3: Acidification.
Dilute \(\mathrm{H_2SO_4}\) acidifies the reaction mixture and gives the final dicarboxylic acid.
The product is benzene-1,4-dicarboxylic acid, commonly called terephthalic acid.
Step 4: Final conclusion.
Hence, the major product formed is
\[ \boxed{\text{Terephthalic acid}} \]
Toluene reacts with acetyl chloride \(\mathrm{CH_3COCl}\) in the presence of anhydrous \(\mathrm{AlCl_3}\).
This is Friedel-Crafts acylation.
Since \(-\mathrm{CH_3}\) group is ortho-para directing, the major product is para-methyl acetophenone.
\[ \mathrm{C_6H_5CH_3 \rightarrow p\text{-}CH_3C_6H_4COCH_3} \]
Step 2: Oxidation with alkaline \(\mathrm{KMnO_4}\).
Strong oxidizing agent \(\mathrm{KMnO_4/KOH}\) oxidizes benzylic side chains to carboxylic acid groups.
Thus, both side chains are converted into \(-\mathrm{COOH}\) groups.
\[ p\text{-}\mathrm{CH_3C_6H_4COCH_3} \rightarrow p\text{-}\mathrm{HOOC-C_6H_4-COOH} \]
Step 3: Acidification.
Dilute \(\mathrm{H_2SO_4}\) acidifies the reaction mixture and gives the final dicarboxylic acid.
The product is benzene-1,4-dicarboxylic acid, commonly called terephthalic acid.
Step 4: Final conclusion.
Hence, the major product formed is
\[ \boxed{\text{Terephthalic acid}} \]
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