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Question
Ortho and para nitrophenols are more acidic than phenol. Draw the resonance structures of the corresponding phenoxide ions.
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Solution
Resonance structures of o-nitrophenoxide ion
Resonance structures of p-nitrophenoxide ion
Resonance structures of phenoxide ion
In substituted phenols, electron-withdrawing groups such as the nitro group increase the acidic strength of phenol. This effect becomes more potent when such groups are present at the ortho and para positions. This is because of the effective delocalisation of the anion of the phenoxide ion. Hence, o- and p-nitrophenols are more acidic than phenol.
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