Consider the progressive halogenation of acetic acid to increase its acidic strength. What is the ma — GOC and Organic Chemistry Basics Chemistry Question
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?
Answer: 3
💡 Solution & Explanation
Acetic acid ($CH_3COOH$) has exactly 3 $\alpha$ -hydrogens on the methyl group. All 3 can be sequentially replaced by highly electronegative chlorine atoms to form trichloroacetic acid ($CCl_3COOH$), which represents the maximum possible $-I$ stabilization for this specific carbon skeleton.
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