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COMEDK · Chemistry · 29. Amines

An organic compound \([\mathrm{X}]\) (molecular formula- \(\mathrm{C}_5 \mathrm{H}_{11} \mathrm{NO}\) when reacted with \(\mathrm{Br}_2 /\) aq. NaOH yielded [Y] which reacts with \(\mathrm{CHCl}_3\) and Ethanolic KOH to produce a foul smelling compound.
Compound \([\mathrm{Y}]\) also reacts with HONO to produce Butan-1-ol with liberation of \(\mathrm{N}_2(\mathrm{~g})\). Identify [X].

  1. A \(\mathrm{CH}_3-\left(\mathrm{CH}_2\right)_2-\mathrm{CO}-\mathrm{CH}_2-\mathrm{NH}_2\)
  2. B \(\mathrm{CH}_3-\left(\mathrm{CH}_2\right)_2-\mathrm{CH}\left(\mathrm{NH}_2\right)-\mathrm{CHO}\)
  3. C \(\mathrm{CH}_3-\left(\mathrm{CH}_2\right)_3-\mathrm{CONH}_2\)
  4. D \(\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CO}-\left(\mathrm{CH}_2\right)_2-\mathrm{NH}_2\)
Verified Solution

Answer & Solution

Correct Answer

(C) \(\mathrm{CH}_3-\left(\mathrm{CH}_2\right)_3-\mathrm{CONH}_2\)

Step-by-step Solution

Detailed explanation

The reaction of compound [X] with \(\mathrm{Br}_2 / \mathrm{aq. NaOH}\) is the Hofmann bromamide degradation reaction, which converts an amide (\(\mathrm{R-CONH}_2\)) into a primary amine (\(\mathrm{R-NH}_2\)). The product [Y] reacts with \(\mathrm{CHCl}_3\) and ethanolic…