The acidity of phenols is determined by the stability of the phenoxide ion formed after losing a proton.
- Electron-Withdrawing Groups (EWG): Groups like −NO2 withdraw electrons, dispersing the negative charge on the oxygen and stabilizing the phenoxide ion, thus increasing acidity.
- para-nitrophenol (d): The −NO2 group exerts both a strong electron-withdrawing resonance effect (−R) and an inductive effect (−I) at the para position. This makes it the most acidic.
- meta-nitrophenol (c): The −NO2 group at the meta position exerts only the electron-withdrawing inductive effect (−I). The resonance effect does not operate at the meta position. Therefore, it is less acidic than the para isomer but more acidic than phenol.
- Standard: Phenol (a) has no substituents and serves as the reference.
- Electron-Donating Groups (EDG): Groups like methyl (−CH3) release electrons (via +I effect and hyperconjugation), intensifying the negative charge on the oxygen and destabilizing the phenoxide ion, thus decreasing acidity.
- Methyl phenol (b): Due to the electron-donating nature of the methyl group, it is less acidic than phenol.
Conclusion: The order of acidity is d > c > a > b.