Consider the progressive halogenation of acetic acid to increase its acidic strength. What is the maximum number of electron-withdrawing chlorine atoms (exerting a effect) that can be substituted for

Question

Consider the progressive halogenation of acetic acid to increase its acidic strength. What is the maximum number of electron-withdrawing chlorine atoms (exerting a $-I$ effect) that can be substituted for $\alpha$ -hydrogens on the methyl group of acetic acid ($CH_3COOH$) to form trichloroacetic acid?

Prashant Kotian · Accepted Answer

Correct answer: 3. Acetic acid () has exactly 3 -hydrogens on the methyl group. All 3 can be sequentially replaced by highly electronegative chlorine atoms to form trichloroacetic acid (), which represents the maximum possible stabilization for this specific carbon skeleton.

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