Given below are two statements:
Statements-I : In Hofmann degradation reaction, the migration of only an alkyl group takes place from carbonyl carbon of the amide to the nitrogen atom.
Statement-II : The group is migrated in Hofmann degradation reaction to electron deficient atom.
In the light of the above statement, choose the most appropriate answer from the options given below:
Statements-I : In Hofmann degradation reaction, the migration of only an alkyl group takes place from carbonyl carbon of the amide to the nitrogen atom.
Statement-II : The group is migrated in Hofmann degradation reaction to electron deficient atom.
In the light of the above statement, choose the most appropriate answer from the options given below:
- (A)Both Statement-I and Statement-II are correct
- (B)Both Statement-I and Statement-II are incorrect
- (C)Statement-I is correct but Statement-II is incorrect
- (D)Statement-I is incorrect but Statement-II is correct✓ Correct
Answer: (D)
Solution
In the Hofmann degradation (Hofmann bromamide reaction), an amide reacts with Br₂ and NaOH to form a primary amine with one carbon less. Statement-I is incorrect because not only alkyl groups but also aryl groups can migrate from the carbonyl carbon to the nitrogen atom. Statement-II is correct: the migration occurs to an electron-deficient nitrogen atom (the nitrene intermediate). The mechanism involves formation of an isocyanate intermediate where the R group migrates to the electron-deficient nitrogen. Therefore, option (D) is correct.
JEE Main · 2022 · 27 Jun 2022 · Shift 1 · Single correct option