Four phenols are shown beside the options (the drawn compound is the parent phenol). Which structure is the weakest acid?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: D

Electron-donating groups destabilise the phenoxide. p-Cresol (pKa about 10.3) is weaker than phenol (10.0); p-chlorophenol (9.4), m-nitrophenol (8.4) and p-nitrophenol (7.2) are stronger.

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