Amines - Result Question 27

####29. 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 $CHCl_3$ and caustic potash gave (C) which on reduction gave isopropylmethylamine. Predict the structure of(A).

(a)

(b) $CH_3 CH_2-NH-CH_3$

(c)CN(C)C

(d) $CH_3 CH_2 CH_2-NH_2$

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Solution:

  1. (a)

CC(C)O[N+][C-]#[N+]C(C)CC(O)C(C)C

(C)CCCC(C)NC

Only primary aliphatic and aromatic amines give carbylamine reaction. Primary amine on reaction with $HNO_2$ give alcohol



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