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COMEDK · Chemistry · 29. Amines

A Nitrogen containing organic compound with molecular formula C\(_3\)H\(_5\)N undergoes the following reactions.
C\(_3\)H\(_5\)N + Na / Hg in C\(_2\)H\(_5\)OH \(\rightarrow\) [A]
[A] + CH\(_3\)COCl / NaOH (aq) \(\rightarrow\) [B]
[A] + CHCl\(_3\) / KOH on heating \(\rightarrow\) [C] (foul smelling compound)
Identify compounds [B] and [C]

  1. A [B]: (CH\(_3\))\(_3\[-\)C\(-\)NH\(-\)COCl    [C]: CH\(_3\]-\)CH\(_2$$-\)CN
  2. B [B]: CH\(_3\[-\)CH\(_2\]-\)NH\(-\)COCH\(_2\[-\)CH\(_3\)    [C]: CH\(_3\]-\)(CH\(_2\))\(_2$$-\)CN
  3. C [B]: (CH\(_3\))\(_2\[-\)CH\(-\)NH\(-\)COCH\(_3\)    [C]: CH\(_3\]-\)CH\(_2$$-\)NC
  4. D [B]: CH\(_3\[-\)(CH\(_2\))\(_2\]-\)NH\(-\)COCH\(_3\)    [C]: CH\(_3\[-\)(CH\(_2\))\(_2\]-\)NC
Verified Solution

Answer & Solution

Correct Answer

(D) [B]: CH\(_3\[-\)(CH\(_2\))\(_2\]-\)NH\(-\)COCH\(_3\)    [C]: CH\(_3\[-\)(CH\(_2\))\(_2\]-\)NC

Step-by-step Solution

Detailed explanation

The molecular formula of the given organic compound is \(C_3H_5N\). Its degree of unsaturation is \(3 + 1 - \dfrac{5}{2} + \dfrac{1}{2} = 2\). The compound undergoes reduction to form [A], which reacts with \(CHCl_3\) and KOH to give a foul-smelling compound [C]. This is the…