Question

In a set of reactions, ethylbenzene yielded a product D. The reaction sequence is:

Ethylbenzene → [KOH] → KMnO₄ → B → [Br₂/FeCl₃] → C → [C₂H₅OH, H⁺] → D

The correct structure of product D is: 

• A. Benzyl bromide ethyl ester
• B. Dibromobenzyl ethyl ester
• C. Ethoxy benzoic acid
• D. Ethyl m-bromobenzoate

Hint:

Strong oxidants convert alkyl side chains on benzene to -COOH, which is meta-directing.

Answer 1

The Correct Option is D

Step 1: Ethylbenzene on oxidation with alkaline KMnO₄ gives benzoic acid (-COOH).
Step 2: Benzoic acid undergoes electrophilic bromination. The -COOH group is meta-directing, so bromination occurs at meta position.
Step 3: Treatment with ethanol in acidic medium gives esterification.
Step 4: Final product is ethyl meta-bromobenzoate.