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Which of the following acid is highly acidic?

  • A.Fluoroacetic acid
  • B.Formic acid
  • C.Dichloroacetic acid
  • D.Benzoic acid
  • E.Acetic acid.

Answer: C

The most acidic is dichloroacetic acid.

Electron-withdrawing halogen atoms near the carboxyl group stabilise the carboxylate anion and increase acidity, and two halogens do more than one. Approximate pKa values:

  • dichloroacetic acid: 1.3
  • fluoroacetic acid: 2.6
  • formic acid: 3.8
  • benzoic acid: 4.2
  • acetic acid: 4.8

Although fluorine is more electronegative than chlorine, two chlorines outweigh one fluorine, so dichloroacetic acid has the lowest pKa.

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