Example 1
Arrange in increasing order of acidic strength: phenol, ethanol, p-nitrophenol, p-cresol.
- 1Ethanol: the ethoxide ion has no resonance, so it is the weakest acid.
- 2Phenoxide is resonance-stabilised; a methyl group (+I, hyperconjugation) in p-cresol destabilises it slightly.
- 3A para-NO₂ group (−R, −I) delocalises the negative charge further, so p-nitrophenol is the strongest.