Question

ortho and para nitrophenoles are more acidic than phenol . DRAW the rrdonance structure of thr corresponding phenol ions.

Answer 1

Resonating structures of o-nitrophenoxide ions that are formed by the loss of proton from o-nitrophenol are as follows:



Resonating structures of p-nitrophenoxide ions that are formed by the loss of proton from p-nitrophenol are as follows:



Resonating structures of phenoxide ions that are formed by the loss of proton from phenol are as follows:



It is clearly evident from the above structures that due to —R-effect of— NO2NO2 group, o-and p-nitrophenoxide ions are more stable than phenoxide ions. Consequently, o- and p-nnitrophenols are more acidic than phenols

Answer 2

Resonating structures of o-nitrophenoxide ions that are formed by the loss of proton from o-nitrophenol are as follows:



Resonating structures of p-nitrophenoxide ions that are formed by the loss of proton from p-nitrophenol are as follows:



Resonating structures of phenoxide ions that are formed by the loss of proton from phenol are as follows:



It is clearly evident from the above structures that due to —R-effect of— NO2NO2 group, o-and p-nitrophenoxide ions are more stable than phenoxide ions. Consequently, o- and p-nnitrophenols are more acidic than phenols.