question_answer

An organic compound "A" having molecular formula \[{{C}_{2}}{{H}_{3}}N\] on reduction gave another compound 'B' Upon treatment with nitrous acid, 'B' gave ethyl alcohol. On warming with chloroform and alcoholic KOH, B formed an offensive smelling compound 'C'. The compound 'C' is

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

B) \[C{{H}_{3}}C{{H}_{2}}N\vec{=}C\]

C) \[C{{H}_{3}}C\equiv N\]

D) \[C{{H}_{2}}C{{H}_{2}}OH\]

Correct Answer: B

Solution :

[b] Given reactions indicate that B has \[1{}^\circ N{{H}_{2}}\]  group, and thus \[A,{{C}_{2}}{{H}_{3}}N\], should be \[C{{H}_{3}}C\equiv N.\] Hence C should be \[C{{H}_{3}}C{{H}_{2}}NC\] \[\underset{A}{\mathop{C{{H}_{3}}C\equiv N}}\,\xrightarrow{reaction}\underset{B}{\mathop{C{{H}_{3}}C{{H}_{2}}N{{H}_{2}}}}\,\xrightarrow[KOH]{CHC{{l}_{3}}}\] \[\underset{C}{\mathop{C{{H}_{3}}C{{H}_{2}}N}}\,\vec{=}C\]