How does chlorine affect the acidity of chloroacetic acid?

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Chlorine increases the acidity of chloroacetic acid through the inductive effect. Because chlorine has a higher electronegativity than hydrogen, it acts as an electron-withdrawing group, drawing electrons in the C–Cl bond away from the carbon atom.

This electron-withdrawing behavior stabilizes the negatively charged carboxylate ion formed when the acid donates a proton. In general, electron-withdrawing groups increase acidity by enhancing the stability of this resulting anion. Consequently, chloroacetic acid is approximately 100 times stronger as an acid than acetic acid, where a hydrogen atom is present instead of chlorine.12