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JEE Advanced levelSingle correct optionDifficulty 3 of 3g1025

Chloroacetic acid (pKa ) is more acidic than acetic acid (pKa ). Assume that the lowering of pKa produced by a chlorine atom is the full alpha effect when Cl is on the alpha carbon (C-2), and that it falls by a factor of for each additional carbon the chlorine moves away from the alpha carbon (beta-chloro, C-3: factor ; gamma-chloro, C-4: factor ). Butanoic acid has pKa . The estimated pKa of 4-chlorobutanoic acid is

  1. A
  2. B
  3. C
  4. D

Answer: B

The alpha-chloro shift is . In 4-chlorobutanoic acid the chlorine is on C-4, two carbons beyond the alpha carbon, so the shift is . The estimated pKa is .
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