Q. 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) (CH₃)₂CH–NH₂
B) CH₃CH₂–NH–CH₃
C) (CH₃)₃N
D) CH₃CH₂CH₂–NH₂
Explanation
[Solution from source] Evolving N₂ with nitrous acid and giving a carbylamine (isocyanide) with CHCl₃/KOH both show A is a primary amine. Reducing (CH₃)₂CH–NC gives (CH₃)₂CH–NH–CH₃ (isopropylmethylamine), so A is isopropylamine, (CH₃)₂CH–NH₂. n-Propylamine would give n-propylmethylamine instead. Answer (1).
Reviewed by Dr. Abubacker
Physics Educator & NEET/JEE Specialist
Ph.D. in Physics with 19+ years of teaching experience.