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Question: Answered & Verified by Expert
Why does acetylation of the -NH2group of aniline reduce its activating effect?
ChemistryAminesNEET
Options:
  • A Acetylation increases the electron density on the nitrogen atom, leading to decreased activation.
  • B Acetylation enhances the resonance stabilization of the amino group, weakening its activating effect.
  • C Because the lone pair on the nitrogen atom is in conjugation with the carbonyl group in acetylated aniline. As a result, the lone pair of electrons on nitrogen is less available for donation to benzene ring by resonance
  • D Acetylation decreases the steric hindrance around the amino group, making it less reactive.
Solution:
1798 Upvotes Verified Answer
The correct answer is: Because the lone pair on the nitrogen atom is in conjugation with the carbonyl group in acetylated aniline. As a result, the lone pair of electrons on nitrogen is less available for donation to benzene ring by resonance
Correct Option is : (C)
Because the lone pair on the nitrogen atom is in conjugation with the carbonyl group in acetylated aniline. As a result, the lone pair of electrons on nitrogen is less available for donation to benzene ring by resonance

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