COMEDK2024ChemistryAminesActual
4-methyl benzamide (A) on reaction with ethanolic solution of KOH and bromine gives another compound (B). The compound (B) on treatment with benzoyl chloride gives compound (C). Identify the correct structure of compound (C) from the following.
Correct answer
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Step-by-step solution
The reaction of 4-methylbenzamide with Br₂ and ethanolic KOH is the Hofmann bromamide degradation reaction. This reaction converts an amide ( R-CONH₂ ) into a primary amine ( R-NH₂ ) with one less carbon atom. Starting with 4-methylbenzamide ( CH₃-C₆H₄-CONH₂ ), the Hofmann bromamide degradation yields 4-methylaniline ( p -toluidine), which is CH₃-C₆H₄-NH₂ . This is compound (B). Compound (B), 4-methylaniline, then reacts with benzoyl chloride ( C₆H₅-COCl ) in the presence of a base (like pyridine or aqueous NaOH )