An organic compound $(C_3H_9N)\,\, (A),$ when treated with nitrous acid, gave an alcohol and $N_2$ gas was evolved. $(A)$ on warming with $CHCl_3$ and caustic potash gave $(C)$ which on reduction gave isopropylmethylamine. Predict the structure of $(A).$

Q: An organic compound $(C_3H_9N)\,\, (A),$ when treated with nitrous acid, gave an alcohol and $N_2$ gas was evolved. $(A)$ on warming with $CHCl_3$ and caustic potash gave $(C)$ which on reduction gave isopropylmethylamine. Predict the structure of $(A).$

a $\underset{(A)}{\mathop{\begin{matrix} C{{H}_{3}}-CH-N{{H}_{2}} \\ |\,\,\,\,\,\, \\ \,C{{H}_{3}} \\ \end{matrix}}}\,$ $\xrightarrow[KOH]{CHC{{l}_{3}}}$ $\underset{(C)}{\mathop{\begin{matrix} C{{H}_{3}}-CH-N\vec{=}C \\ |\,\,\,\,\,\,\,\, \\ C{{H}_{3}}\, \\ \end{matrix}}}\,$ $\xrightarrow{\operatorname{Re}duction}$ $\begin{matrix} C{{H}_{3}}-CH-NH-C{{H}_{3}} \\ \,\,|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\ \,\,C{{H}_{3\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,}}\,\, \\ \end{matrix}$

Question

A
B$CH_3CH_2 - NH - CH_3$
C$\begin{array}{*{20}{c}}
{C{H_3} - N - C{H_3}} \\
| \\
{C{H_3}}
\end{array}$
D$CH_3CH_2CH_2 - NH_2$

AIPMT 2012, Medium

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