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Question

Explain why is ortho nitrophenol more acidic than ortho methoxyphenol?

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Solution

In ortho nitro phenol, electron withdrawing nitro group is present in ortho position, the electron density of OH bond is reduced.
This makes removal of proton easy. After deprotonation, o-nitrophenoxide ion is resonance stabilized. Hence, ortho nitrophenol is a stronger acid.
In ortho methoxyphenol, electron releasing methoxy group is present in ortho position, the electron density of OH bond is increased.
This makes removal of proton difficult. Hence, ortho methoxyphenol is less acidic.

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