Which of the following statements is not correct?

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The resonance stabilization of phenol is more than that of phenoxide ion

p-Aminophenol is less acidic than phenol.

The heating of an ester of phenol with aluminum chloride causes rearrangement of the acyl group from the phenolic oxygen to an ortho or para position of the ring.

If halogenation of phenol is carried out in a less polar medium such as ${CHCl}_{3}, {CCl}_{4}$ or ${CS}_{2}$ , only monohalogenated products are obtained

answer is A.

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Detailed Solution

(a) The resonating structures of phenol involve charge separation while those of phenoxide ion do not involve any charge separation. Since energy is needed to separate opposite charges, the structures of phenol involve more energy and thus are less stable than the structures of phenoxide ion.

(b) Electron-releasing substituent destabilizes the phenoxide ion, hence, making such substituted phenol less acidic.

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