The acidity of phenols is determined by the stability of the phenoxide ion formed after the loss of a proton.
- Electron Withdrawing Groups (EWG): Substituents like the nitro group (−NO2) exert electron-withdrawing inductive (−I) and resonance (−R) effects . These effects disperse the negative charge on the oxygen of the phenoxide ion, stabilising it and thus increasing the acidity of the parent phenol.
- Electron Donating Groups (EDG): Alkyl groups like methyl (−CH3) exert an electron-releasing inductive effect (+I) , which intensifies the negative charge on the phenoxide ion, destabilising it and decreasing acidity.
- Comparison:
- o-Cresol: Contains a methyl group (+I effect), making it less acidic than phenol.
- Phenol: Standard reference.
- p-Nitrophenol: Contains one −NO2 group, making it more acidic than phenol.
- 2,4,6-Trinitrophenol (Picric Acid): Contains three strong electron-withdrawing −NO2 groups at ortho and para positions. The cumulative −I and −R effects provide maximum stabilisation to the phenoxide ion, making it the most acidic compound among the options.