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JEE Main levelSingle correct optionDifficulty 2 of 3g2074

When acetamide, , is protonated in strong acid, the proton adds mainly to

  1. Athe nitrogen, because it has a lone pair
  2. Bthe methyl carbon
  3. Cthe carbonyl oxygen, because the resulting cation is stabilised by resonance with nitrogen
  4. Dthe nitrogen, because oxygen is more electronegative

Answer: C

Protonation at O gives , a resonance-stabilised cation in which the positive charge is shared by O and N. Protonation at N would leave the N lone pair unavailable for conjugation and the cation would be unstabilised, so O-protonation is favoured.
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