The acidic strength of phenols is governed by the stability of the phenoxide ion formed after the loss of a proton.
- Electron-Withdrawing Groups (EWG): Substituents like −NO2, −CN, and halogens withdraw electrons from the benzene ring (via −I and −R effects). This delocalises the negative charge on the phenoxide oxygen, stabilizing the ion and increasing acidity , .
- Electron-Donating Groups (EDG): Substituents like alkyl groups (e.g., −CH3) or alkoxy groups release electrons (via +I or +R effects). This intensifies the negative charge on the phenoxide oxygen, destabilizing the ion and decreasing acidity.
Given the correct order III > I > II, it can be inferred that:
- Compound (III) likely contains an electron-withdrawing group (making it the most acidic).
- Compound (II) likely contains an electron-donating group (making it the least acidic).
- Compound (I) is likely the unsubstituted phenol or has an intermediate substituent effect.