question_answer

An organic compound \[({{C}_{3}}{{H}_{9}}N)\] , when treated with nitrous acid, gave an alcohol and N2 gas was evolved. on warming with \[CHC{{l}_{3}}\] and caustic potash gave (C which on reduction gave iso-propylmethylamine. Predict the structure of.[AIPMT (M) 2012]

A)

B) \[C{{H}_{3}}C{{H}_{2}}-NH-C{{H}_{3}}\]

C) \[\text{C}{{\text{H}}_{\text{3}}}-\underset{\begin{smallmatrix}  \text{ }\!\!|\!\!\text{ } \\  \text{C}{{\text{H}}_{\text{3}}} \end{smallmatrix}}{\mathop{\text{N}}}\,-\text{C}{{\text{H}}_{\text{3}}}\]        

D) \[C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}-N{{H}_{2}}\]

Correct Answer: A

Solution :

[a] On treating with nitrous acid primary a mine gives an alcohol and \[{{N}_{2}}\] gas. So,' A' should be a primary amine.

\[{{C}_{3}}{{H}_{7}}N{{H}_{2}}+HN{{O}_{2}}\xrightarrow{NaN{{O}_{2}}+HCl}{{C}_{3}}{{H}_{7}}OH\]            \[+{{N}_{2}}+{{H}_{2}}O\]