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COMEDK · Chemistry · 29. Amines

An organic compound \(\mathrm{A}\left(\mathrm{C}_5 \mathrm{H}_9 \mathrm{~N}\right)\) upon reaction with \(\mathrm{Na} / \mathrm{Hg} / \mathrm{C}_2 \mathrm{H}_5 \mathrm{OH}\) gives compound B . B reacts with \(\mathrm{NaNO}_2 / \mathrm{HCl}\) at 274 K to form C with quantitative liberation of \(\mathrm{N}_2\) gas. B also reacts with Hinsberg's reagent to form a compound which is soluble in alkali. Identify compound B.

  1. A \(\mathrm{CH}_3-\left(\mathrm{CH}_2\right)_2-\mathrm{N}-\left(\mathrm{CH}_3\right)_2\)
  2. B \(\mathrm{CH}_3-\left(\mathrm{CH}_2\right)_3-\mathrm{NH}-\mathrm{CH}_3\)
  3. C \(\mathrm{CH}_3-\left(\mathrm{CH}_2\right)_4-\mathrm{NH}_2\)
  4. D \(\left[\left(\mathrm{CH}_3\right)_3-\mathrm{N}-\mathrm{CH}_2 \mathrm{CH}_3\right]^{+}\)
Verified Solution

Answer & Solution

Correct Answer

(C) \(\mathrm{CH}_3-\left(\mathrm{CH}_2\right)_4-\mathrm{NH}_2\)

Step-by-step Solution

Detailed explanation

Two key reactions of B: 1. Reacts with \(NaNO_2/HCl\) at 274 K to liberate \(N_2\) quantitatively \(\Rightarrow\) characteristic of a primary aliphatic amine (\(R-NH_2 + HNO_2 \rightarrow R-OH + N_2\uparrow + H_2O\)) 2. Reacts with Hinsberg's reagent to form a product soluble in…