Identify the amine that does not form alcohol by the action of $\mathrm{NaNO}_2$ and $\mathrm{HCl}$.

Identify the amine that does not form alcohol by the action of $\mathrm{NaNO}_2$ and $\mathrm{HCl}$.
  1. $\left(\mathrm{CH}_3\right)_3-\mathrm{C}-\mathrm{NH}_2$
  2. $\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{NH}_2$
  3. \(\mathrm{CH}_3-\underset{|~~~~\atop \large \mathrm{NH}_2}{\mathrm{CH}}-\mathrm{CH}_3\)
  4. $\left(\mathrm{CH}_3\right)_2-\mathrm{NH}$

Solution

$\mathrm{R}-\mathrm{NH}_2 \stackrel{\mathrm{NaNO}_2+\mathrm{HCl}}{\longrightarrow} \mathrm{R}-\mathrm{OH}+\mathrm{N}_2+\mathrm{H}_2 \mathrm{O}$ Thus, $\left(\mathrm{CH}_2\right)-\mathrm{NH} \rightarrow 2^{\circ}$ amine, do not give alcohol with $\mathrm{NaNO}_2$ \& $\mathrm{HCl}$.

Asked in: MHT CET 2022 (11 Aug Shift 1)

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