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NCERT Class XII Chemistry
Chapter - Alcohols, Phenols and Ethers
Questions with Solutions

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Question : 15 of 45
Marks: +1, -0
Explain why is ortho nitrophenol more acidic than methoxyphenol?
Solution:  
The acidity of phenol arises from the loss of H of O – H group as H+\mathrm{H}^{+} . This loss is facilitated if the polarity of the O – H bond increases and H carries substantial δ+\delta^{+} charge.
In (I), the presence of the highly electron withdrawing NO2\mathrm{NO}_2group at the ortho position increases the polarity of the O – H bond.
This helps in release of H+^{+} and increases acidity. (II) is less acidic because −OCH3\mathrm{-OCH}_3 is an electron releasing group and increases the e−^{-} density on O of OH and H+^{+} release is suppressed.
This can be understood from the resonance structures of II which are
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