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Explain why is ortho nitrophenol more acidic than ortho methoxyphenol?
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In ortho nitro phenol, electron withdrawing nitro group is present in ortho position, the electron density of 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 bond is increased.
This makes removal of proton difficult. Hence, ortho methoxyphenol is less acidic.
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 bond is increased.
This makes removal of proton difficult. Hence, ortho methoxyphenol is less acidic.
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Question Text | Explain why is ortho nitrophenol more acidic than ortho methoxyphenol? |
Updated On | Feb 20, 2023 |
Topic | Alcohols, Phenols and Ethers |
Subject | Chemistry |
Class | Class 12 |
Answer Type | Text solution:1 Video solution: 6 |
Upvotes | 694 |
Avg. Video Duration | 12 min |