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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 isopropylmethylamine. Predict the structure of (A).

CH3−N|CH3−CH3

CH3CH2−NH−CH3

CH3CH2CH2−NH2

(CH3)2−CH−NH2

Solution:

CH3−CH|CH3(A)−NH2CHCl3−−−−−−−→KOHCH3−CH|CH3(C)−N−−−−→ReductionCH3−CH|CH3−NH−CH3
Hence, option D is correct.