1. Tardigrade
  2. Question
  3. Chemistry
  4. 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).

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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 isopropylmethyl amine. Predict the structure of $(A)$.

AIPMTAIPMT 2012Amines

Solution:

As $(A)$ gives alcohol on treatment with nitrous acid thus, it should be primary amine. $C_3H_9N$ has two possible structures with $-NH_2$ group.
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As it gives isopropylmethyl amine thus it should be isopropyl amine not n-propyl amine.
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