JEE MainChemistryAmines
An organic compound 1-ethyl-4-nitrobenzene is subjected to the following sequence of reactions: (i) Sn/HCl (ii) NaNO ₂ /HCl at 0-5^ C (iii) KI (iv) KMnO ₄ /KOH , , followed by H ₃ O ^+ (v) Br ₂ /FeBr ₃ The major final product formed is:
Options
- A2-bromo-4-iodobenzoic acid
- B(3-bromo-4-iodophenyl)acetic acid
- C3-bromo-4-iodobenzoic acid
- D3-bromo-4-ethylnitrobenzene
Correct answer
C. 3-bromo-4-iodobenzoic acid
Step-by-step solution
The reaction sequence proceeds as follows: 1. Reduction: 1-ethyl-4-nitrobenzene is reduced by Sn/HCl to 4-ethylaniline. 2. Diazotization: 4-ethylaniline reacts with NaNO ₂ /HCl at 0-5^ C to form the corresponding diazonium salt. 3. Substitution: Treatment with KI replaces the diazonium group with iodine, yielding 1-ethyl-4-iodobenzene. 4. Side-chain oxidation: KMnO ₄ /KOH followed by acidification oxidizes the ethyl side chain entirely to a carboxylic acid group, producing 4-iodobenzoic acid. 5. Electrophilic aroma