JEE MainChemistryAmines
An aromatic amide A with the molecular formula C₇H₇NO is treated with Br₂ and aqueous NaOH to give compound B . Compound B is then reacted with Hinsberg's reagent to form compound C , which is found to be soluble in aqueous NaOH . Determine the number of carbon atoms present in one molecule of compound C .
Correct answer
12
Step-by-step solution
The aromatic amide A with molecular formula C₇H₇NO is benzamide ( C₆H₅CONH₂ ). Treatment of benzamide with Br₂ and aqueous NaOH brings about the Hoffmann bromamide degradation reaction. In this reaction, the carbonyl carbon is lost as carbonate, yielding aniline ( C₆H₅NH₂ ) as compound B . Aniline is a primary amine. It reacts with Hinsberg's reagent, which is benzenesulfonyl chloride ( C₆H₅SO₂Cl ), to form N-phenylbenzenesulfonamide as compound C . The reaction is: C₆H₅NH₂ + C₆H₅SO₂Cl C₆H₅-NH-SO₂-C₆H₅ + HCl Compou