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].
- A \(\mathrm{CH}_3-\left(\mathrm{CH}_2\right)_2-\mathrm{CO}-\mathrm{CH}_2-\mathrm{NH}_2\)
- B \(\mathrm{CH}_3-\left(\mathrm{CH}_2\right)_2-\mathrm{CH}\left(\mathrm{NH}_2\right)-\mathrm{CHO}\)
- C \(\mathrm{CH}_3-\left(\mathrm{CH}_2\right)_3-\mathrm{CONH}_2\)
- D \(\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CO}-\left(\mathrm{CH}_2\right)_2-\mathrm{NH}_2\)
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…
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