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 caustiv potash gave `(C)` which on reduction gave isopropylmethylamine. Predict the structure of (A).

Options

A.
B. `CH_(3)CH_(2)-NH-CH_(3)`
C. `CH_(3)-underset(H_(3)C) underset(|)(N)-CH_(3)`
D. `CH_(3)CH_(2)CH_(2)-NH_(2)`

Answer

A

Explanation

As A gives alcohol on treatment with nitrous acid thus it should be primary amine. `C_(2)H_(9)N` has two possible structure with `-NH_(2)` group.
`CH_(3)-CH_(3)-CH_(2)-NH_(2) " or " CH_(3)-underset(CH_(3))underset(|)(C )H-NH_(3)`
As it gives isopropylmethylamine thus it should isopropyl amine not n-propyl amine
`CH_(3)-underset((A))underset(CH_(3))underset(|)(C )H overset(HNO_(2)) to CH_(3)-underset(CH_(3))underset(|)(C )H-CH_(3)+N_(2)uarr overset(CHCl_(2)//KOH) to`
`CH_(3)-underset((B))underset(CH_(3))underset(|)(C )H-NC overset("Reduction") to CH_(3)-underset("Isopropylmethylamine")underset(CH_(3))underset(|)(C )H-NH-CH_(3)`