Which of the following is most acidic?

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Question

(C) The acidity of phenols is determined by the stability of the phenoxide ion formed after the loss of a proton. Electron-withdrawing groups $(EWG)$

Vedclass · Accepted Answer

$m$-chlorophenol

Vedclass · Answer

(C) The acidity of phenols is determined by the stability of the phenoxide ion formed after the loss of a proton. Electron-withdrawing groups $(EWG)$ like $-Cl$ increase the acidity of phenols by stabilizing the phenoxide ion through the inductive effect. Benzyl alcohol and cyclohexanol are not acidic in nature as they do not form stable phenoxide-like ions. Between phenol and $m$-chlorophenol,the presence of the $-Cl$ group in $m$-chlorophenol exerts an electron-withdrawing inductive effect ($-I$ effect),which stabilizes the conjugate base more than in unsubstituted phenol. Therefore,$m$-chlorophenol is the most acidic among the given options.

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