Amines - Result Question 27

####29. 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 isopropylmethylamine. Predict the structure of(A).

(a)

(b) CH3CH2−NH−CH3

(c)CN(C)C

(d) CH3CH2CH2−NH2

Show Answer

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 HNO2 give alcohol

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