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JEE Main levelSingle correct optionDifficulty 2 of 3nc157

Acetanilide undergoes electrophilic substitution less readily than aniline mainly because

  1. Athe nitrogen lone pair is delocalised onto the carbonyl oxygen and is less available to the ring
  2. Bacetanilide has no lone pair on nitrogen
  3. Cthe acetyl group is a meta-directing group on the ring
  4. Dacetanilide is a stronger base than aniline

Answer: A

In acetanilide the nitrogen lone pair is shared between the ring and the C=O group by resonance, so the activating +R effect on the ring is reduced. The group is still ortho, para directing. Acetanilide is also a weaker base than aniline.
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