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JEE Main levelSingle correct optionDifficulty 2 of 3g2255

Which hydrogen atoms of the compound shown are the most acidic?

  1. Athe CH2 hydrogens next to the NO2 group
  2. Bthe CH2 hydrogens next to the C=O
  3. Cthe NH2 hydrogens of the amide
  4. Dthe NH2 hydrogens and the CH2 next to C=O are equally acidic

Answer: A

The CH2 attached to the nitro group (pKa about 10) gives a nitronate stabilised strongly by NO2. The amide N-H (about 17 in water, higher in practice) and the CH2 alpha to the amide C=O (about 26) are much less acidic.
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