COMEDK202510 May 2025Morning ShiftChemistryAminesActual
An organic compound [ X ] (molecular formula- C ₅ H ₁₁ NO when reacted with Br ₂ / aq. NaOH yielded [Y] which reacts with CHCl ₃ and Ethanolic KOH to produce a foul smelling compound. Compound [ Y ] also reacts with HONO to produce Butan-1-ol with liberation of N ₂( ~g ) . Identify [X].
Options
- ACH ₃- ( CH ₂ )₂- CO - CH ₂- NH ₂
- BCH ₃- ( CH ₂ )₂- CH ( NH ₂ )- CHO
- CCH ₃- ( CH ₂ )₃- CONH ₂
- DCH ₃- CH ₂- CO - ( CH ₂ )₂- NH ₂
Correct answer
C. CH ₃- ( CH ₂ )₃- CONH ₂
Step-by-step solution
The reaction of compound [X] with Br ₂ / aq. NaOH is the Hofmann bromamide degradation reaction, which converts an amide ( R-CONH ₂ ) into a primary amine ( R-NH ₂ ). The product [Y] reacts with CHCl ₃ and ethanolic KOH to produce a foul-smelling compound (isocyanide test), confirming that [Y] is a primary aliphatic amine. The reaction of [Y] with HONO (nitrous acid) produces Butan-1-ol with the liberation of N ₂ gas. This indicates that the amine [Y] is Butan-1-amine, CH ₃- CH ₂- CH ₂- CH ₂- NH ₂ . Since the Hofma