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Question -

Explain why is┬аortho┬аnitrophenolmore acidic than┬аortho┬аmethoxyphenol?



Answer -

The nitro-group is an electron-withdrawinggroup. The presence of this group in the ortho position decreases the electrondensity in the OтИТH bond. As a result, it is easier to lose a proton. Also,the┬аo-nitrophenoxide ion formed after the loss of protons isstabilized by resonance. Hence,┬аortho┬аnitrophenol is astronger acid.

On the other hand, methoxy group is an electron-releasinggroup. Thus, it increases the electron density in the OтИТH bond and hence, theproton cannot be given out easily.

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