Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Amines

Question:

An aromatic compound (A) on treatment with aqueous ammonia and heating forms compound (B) which on heating with Br2 and KOH forms a compound (C) of molecular formula C6H7N.  

Identify (C) from the given reaction. 

Options:

Benzaldehyde

Benzamide 

diprop-2-ynylamine

None of the above 

Correct Answer:

None of the above 

Explanation:

The correct answer is option 4- None of the above

  1. A is likely benzoyl chloride or benzoic acid, which on reacting with aqueous ammonia and heating gives benzamide (B).

  2. Compound B (benzamide) when heated with Br₂ and KOH undergoes Hofmann bromamide reaction, which removes the carbonyl carbon and converts the amide into an amine.

    • So, C = aniline (C₆H₅NH₂), which matches the molecular formula C₆H₇N.

  • Option 1 (Benzaldehyde): This is an aldehyde (C6H5CHO). The reaction Br2/KOH with an amide specifically produces an amine, not an aldehyde.

  • Option 2 (Benzamide): This is Compound (B), the intermediate. You must complete the second step of the reaction to find (C).

  • Option 3 (diprop-2-ynylamine): While this has the formula C6H7N, it is an aliphatic (non-aromatic) secondary amine. Since the starting material (A) was aromatic, the product must retain the benzene ring.

  • Option 4 ( None of above ) is CORRECT