Why is the phenoxide ion more stable than phenol?

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Phenol and phenoxide ion both are stabilized by resonance.

In case of phenol, the lone pair on oxygen atom get delocalize over the benzene ring and this causes a charge separation, i.e., positive charge on oxygen atom while negative charge is on the benzene ring.

phenoxide ion

This type of resonance structures have small contributions to the hybrid in stabilizing the compound.

While in case of phenoxide ion, the negative charge on the oxygen atom get delocalize and no such charge separation takes place.

Therefore, the resonance structures of phenoxide ion has more contribution towards the hybrid in stabilizing the phenoxide ion.

Hence phenoxide ion is more stable than phenol.

Read more: Circle represent most acidic hydrogen in these molecules. Which of the following is correct representation?

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