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Question

Chloroacetic acid is a stronger acid than acetic acid. Give one reason.

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Solution

Chloroacetic acid ClCH2COOH is the strongest acid than acetic acid.

Chlorine is a strong electron-withdrawing group, that pulls the negative charge towards itself by inductive effect so that the negative charge density on the oxygen atom is reduced, hence stabilizing the conjugate base of chloroacetic acid.

The relative stability of the conjugate bases is responsible for the strength of their respective acids. In the case of chloro acetic acid, due to the —I effect of a chlorine atom, the conjugate base of chloro acetic acid gets stability. On the other hand, in the case of acetic acid, the stability of acetate anion is the conjugate base of acetic acid becomes less stable due to+ I effect of the methyl group. Hence chloro acetic acid is more acidic than acetic acid.


The above structures show inductive effects in both acetic acid and chloroacetic acid.



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