Question

Acetanilide is less reactive than aniline toward electrophilic substitution. Explain

Answer 1

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In acetanilide, resonance delocalization of the nitrogen lone pair electrons to·the aromatic ring is less favored because the positive charge on nitrogen is next to the positively polarized carbonyl group. Resonance delocalization to the carbonyl oxygen is favored because of the electronegativity of oxygen. Since the nitrogen lone pair electrons are less available to the ring than in aniline, the · reactivity of the ring toward electrophilic substitution decreases.

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