plz explain me that why ortho nitrophenol is more acidic than ortho methoxyphenol?

Asked by manishasharma1912 | 28th Apr, 2014, 10:25: PM

Expert Answer:

Ortho nitrophenol is more acidic than ortho methoxyphenol. This is because-

The nitro-group is an electron-withdrawing group. The presence of this group in the ortho position in ortho nitro phenol decreases the electron density in the O−H bond. As a result, it is easier to lose a proton.

Also, the o-nitrophenoxide ion formed after the loss of protons is stabilized by resonance. Hence, ortho nitrophenol is a stronger acid.

In the case of ortho methoxyphenol; methoxy group is an electron-releasing group. Thus, it increases the electron density in the O−H bond and hence, the proton cannot be given out easily.

Hence, ortho-nitrophenol is more acidic than ortho-methoxyphenol.

Answered by  | 29th Apr, 2014, 10:24: AM

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