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Question

Explain why p-nitrophenol is more acidic than phenol?

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Solution

Nitro group of phenol produces - I and - R effect. Because of these two effects - NO2 group is electron withdrawing in nature. So, the electron density in the O - H bond of p - nitrophenol decreases relative to the O - H bond of phenol.
The decrease in electron density of the O - H bond of p-nitrophenol, the polarity of O - H bond decreases. The electron withdrawing group (-NO ), withdraws electrons and disperses the negative charge. Therefore, -NO group stabilizes the phenoxide ion. Hence p-nitrophenol is more acidic than phenol.


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