An organic compound A on treatment with NH3 gives B, which on heating gives C. C when treated with Br2 in the presence of KOH produces ethyl amine. Compound A is
- CH3COOH
- CH3CH2CH2COOH
- [figure]
- CH3CH2COOH
Answer
(4) CH3CH2COOH
Solution
Hoffmann bromamide degradation: RCONH2 + Br2 + 4KOH RNH2 + K2CO3 + 2KBr + 2H2O
∵ The amine formed has one carbon atom less than the amide
⇒ Ethyl amine (CH3CH2NH2) comes from propanamide, C = CH3CH2CONH2
Propanamide is obtained by heating ammonium propanoate (B), which is formed from propanoic acid and NH3:
CH3CH2COOH NH3 CH3CH2COO-NH4+ CH3CH2CONH2 Br2/KOH CH3CH2NH2
∴ A = CH3CH2COOH
Answer: (4)