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JEE Main levelSingle correct optionDifficulty 2 of 3g2022

The pKa values of oxalic acid () in water are and . The second dissociation is much weaker because

  1. Athe second carboxyl group is less electronegative than the first
  2. Boxalate ion cannot be stabilised by resonance, while the hydrogenoxalate ion can
  3. CH+ must be removed from an anion, which is harder because of the negative charge already present
  4. Dthe -I effect of the carboxyl group is lost after the first ionisation, so the molecule becomes a stronger electron donor to carbon

Answer: C

After the first ionisation the species is . Removing a proton from it gives a dianion, and the electrostatic attraction of the existing negative charge for H+ plus the repulsion in the dianion make this step less favourable. Hence , with a difference of 3.02 units here.
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