An organic compound (C3H9N) (A), when treated with nitrous acid, gave an alcohol and N2 gas was evolved. (A) on warming with CHCl3 and caustic potash gave (C) which on reduction gave isopropylmethyl amine. Predict the structure of (A).

Question

An organic compound (C3H9N) (A), when treated with nitrous acid, gave an alcohol and N2 gas was evolved. (A) on warming with CHCl3 and caustic potash gave (C) which on reduction gave isopropylmethyl amine. Predict the structure of (A). (A)  (B) CH3CH2—NH—CH3 (C)  (D) CH3CH2CH2-NH2

Tardigrade Admin · Accepted Answer

As (A) gives alcohol on treatment with nitrous acid thus, it should be primary amine. C3H9N has two possible structures with -NH2 group.

As it gives isopropylmethyl amine thus it should be isopropyl amine not n-propyl amine.

Q. An organic compound $(C_{3} H_{9} N)$ $(A)$ , when treated with nitrous acid, gave an alcohol and $N_{2}$ gas was evolved. $(A)$ on warming with $C H C l_{3}$ and caustic potash gave $(C)$ which on reduction gave isopropylmethyl amine. Predict the structure of $(A)$ .

$C H_{3} C H_{2} — N H — C H_{3}$

$C H_{3} C H_{2} C H_{2} - N H_{2}$

As $(A)$ gives alcohol on treatment with nitrous acid thus, it should be primary amine. $C_{3} H_{9} N$ has two possible structures with $- N H_{2}$ group.

As it gives isopropylmethyl amine thus it should be isopropyl amine not n-propyl amine.

Q. An organic compound (C3​H9​N) (A), when treated with nitrous acid, gave an alcohol and N2​ gas was evolved. (A) on warming with CHCl3​ and caustic potash gave (C) which on reduction gave isopropylmethyl amine. Predict the structure of (A).

CH3​CH2​—NH—CH3​

CH3​CH2​CH2​−NH2​

As (A) gives alcohol on treatment with nitrous acid thus, it should be primary amine. C3​H9​N has two possible structures with −NH2​ group. As it gives isopropylmethyl amine thus it should be isopropyl amine not n-propyl amine.

Q. An organic compound $(C_{3} H_{9} N)$ $(A)$ , when treated with nitrous acid, gave an alcohol and $N_{2}$ gas was evolved. $(A)$ on warming with $C H C l_{3}$ and caustic potash gave $(C)$ which on reduction gave isopropylmethyl amine. Predict the structure of $(A)$ .

$C H_{3} C H_{2} — N H — C H_{3}$

$C H_{3} C H_{2} C H_{2} - N H_{2}$

As $(A)$ gives alcohol on treatment with nitrous acid thus, it should be primary amine. $C_{3} H_{9} N$ has two possible structures with $- N H_{2}$ group.

As it gives isopropylmethyl amine thus it should be isopropyl amine not n-propyl amine.