An organic compound A upon reacting with NH3 gives B. On heating B give C, C in presence of KOH reacts with Br2 to give CH3CH2NH2. A is :
(Hoffmann Bromide)
This question involves identifying an organic compound through a series of reactions. Let's analyze the reaction sequence step by step:
Step 1: Compound A reacts with NH3 to give B. This suggests that A is a carboxylic acid, and B is the corresponding ammonium salt.
General reaction:
Step 2: Heating B gives C. When ammonium carboxylate salts are heated, they undergo dehydration to form amides.
General reaction:
So C is an amide: RCONH2
Step 3: C (amide) in presence of KOH reacts with Br2 to give CH3CH2NH2 (ethylamine). This is the Hofmann bromamide reaction, which converts amides to primary amines with one less carbon atom.
General reaction:
Since the final product is CH3CH2NH2 (ethylamine), the amide C must be CH3CH2CONH2 (propanamide). Therefore, the original carboxylic acid A must be CH3CH2COOH (propanoic acid).
Final Answer: A is CH3CH2COOH
Carboxylic Acids: Organic compounds containing the carboxyl functional group (-COOH). They react with bases like ammonia to form salts.
Amides: Derivatives of carboxylic acids where the -OH group is replaced by -NH2. They can be prepared by heating ammonium salts of carboxylic acids.
Hofmann Bromamide Reaction: An important reaction where amides are converted to primary amines with one less carbon atom using bromine and potassium hydroxide.
Formation of ammonium salt: R-COOH + NH3 → R-COO-NH4+
Formation of amide: R-COO-NH4+ → R-CONH2 + H2O (on heating)
Hofmann degradation: R-CONH2 + Br2 + 4KOH → R-NH2 + 2KBr + K2CO3 + 2H2O