Q38 / 180 · KCET 2010 · Chemistry

Chloroacetic acid is a stronger acid than acetic acid. This can be explained using

  • A
    - M effect
  • Correct answer
    B
    - I effect
  • C
    $+\mathrm{M}$ effect
  • D
    + I effect

Solution

-Cl is an electron withdrawing (ie, $-I$ showing) group. It withdraws electrons when attached to the carboxylic acid and decreases the electron density on the oxygen atom. This will facilitate the release of $\mathrm{H}^{+}$by making $\mathrm{O}-\mathrm{H}$ bond more polar and thus $-\mathrm{Cl}$ increases the acidity of acetic acid when attached at, $\alpha$ position because of -I effect.

Hence, the correct answer is option: 'B'.

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