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)
- [figure]
- CH3CH2-NH-CH3
- [figure]
- CH3CH2CH2-NH2
Answer
(1) [figure]
Solution
(A) gives an alcohol and N2 with nitrous acid ⇒ (A) is a primary aliphatic amine, R-NH2.
Carbylamine reaction: R-NH2 + CHCl3 + 3KOH R-NC + 3KCl + 3H2O
Reduction of the isocyanide (C): R-NC 4[H] R-NH-CH3
∵ The product is isopropylmethylamine, (CH3)2CH-NH-CH3 ⇒ R = isopropyl.
∴ (A) = (CH3)2CH-NH2 (isopropylamine, C3H9N).
Answer: (1)