The compound shown is more acidic than phenol. Which statement gives the correct reason?

AThe nitro group withdraws electrons by resonance and induction and so stabilises the phenoxide ion.
BThe nitro group donates electrons to the ring and stabilises the O-H bond.
CThe nitro group makes the molecule heavier and so easier to ionise.
DThe nitro group forms an intramolecular hydrogen bond with the O-H group in the para position.

Answer: A

The compound is 4-nitrophenol. In its anion the negative charge is delocalised onto the nitro group through the

- M

and

- I

effects, which makes the phenoxide more stable and the phenol more acidic. A para nitro group cannot reach the O-H group, and the group is not electron donating.

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The compound shown is more acidic than phenol. Which statement gives the correct reason?

Answer: A

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