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Explain why is ortho-nitrophenol more ac...

Explain why is ortho-nitrophenol more acidic than ortho-methoxyphenol ?

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Due to strong -R and -I-effect of the `-NO_(2)` group, electron density in the O-H bond decreases and hence the loss of a proton becomes easy.

Further, after the loss of a proton, the o-nirophenoxide ion left behind is stabilized by resonance, thereby making o-nitrophenol a stronger acid.

In contrast, due to +R effect of the `OCH_(3)` group, the electron density in the O-H bond increases thereby making the loss of a proton difficult.

Furthermore, the o-methoxyphenoxide ion left after the loss of a proton is destabilized by resonance

because the two negative charges repel each other thereby making o-methoxyphenol a weaker acid. thus, onitrophenol is more acidic than o-methoxyphenol.
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PRADEEP-ALCOHOLS, PHENOLS AND ETHERS-NCERT QUESTIONS AND EXERCISES WITH ANSWERS (NCERT EXERCISES)
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