Discussion
The compound with the lowest pKa value is
Answer: C
The compound with the lowest pKa (strongest acid) is p-nitrophenol.
The nitro group is strongly electron-withdrawing. In the para position it pulls charge out of the ring by both inductive and resonance effects and stabilises the phenoxide ion, so p-nitrophenol loses its proton most easily (pKa about 7.1).
Phenol is weaker (about 10.0). Methyl groups donate electrons, so o- and p-cresol are weaker still, and ethanol (about 16) is the weakest acid of all here.
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