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Which of the following is the weakest acid?

  • A.\(\mathrm{FCH_{2}COOH}\)
  • B.\(\mathrm{NC - CH_{2}COOH}\)
  • C.\(\mathrm{Cl_{3}C - COOH}\)
  • D.\(\mathrm{O_{2}N - CH_{2}COOH}\)
  • E.\(\mathrm{Cl_{2}CHCOOH}\)

Answer: A

The weakest acid is FCH2COOH.

Electron-withdrawing groups strengthen a carboxylic acid by stabilising the carboxylate anion. Fluoroacetic acid (pKa about 2.6) has only one electron-withdrawing substituent.

The others are stronger: cyanoacetic (about 2.5) and nitroacetic (about 1.7) acids carry groups that withdraw by both inductive and resonance effects, dichloroacetic acid (about 1.3) has two chlorines, and trichloroacetic acid (about 0.7) has three.

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