1
Question
Ortho and para nitrophenols are more acidic than phenol. Draw the resonance structures of the corresponding phenoxide ions.
Ortho and para nitrophenols are more acidic than phenol. Draw the resonance structures of the corresponding phenoxide ions.
Open in App
Solution
Resonance structure of ortho−nitrophenol
Resonating structures of o−nitrophenol ions that are formed by the loss of a proton from o−nitrophenol are as follows:
Resonance structure of para−nitrophenol
Resonating structures of p−nitrophenoxide ions that are formed by the loss of a proton from p-nitrophenol are as follows:
Conclusion
Due to stabilization via −R effect of −NO2 group,o− and p−nitrophenoxide ions are more stable than phenoxide ion. And we know that stable the conjugate base, stronger the corresponding acid
This is why ortho and para nitrophenols are more acidic than phenol.
Resonating structures of o−nitrophenol ions that are formed by the loss of a proton from o−nitrophenol are as follows:
Resonance structure of para−nitrophenol
Resonating structures of p−nitrophenoxide ions that are formed by the loss of a proton from p-nitrophenol are as follows:
Conclusion
Due to stabilization via −R effect of −NO2 group,o− and p−nitrophenoxide ions are more stable than phenoxide ion. And we know that stable the conjugate base, stronger the corresponding acid
This is why ortho and para nitrophenols are more acidic than phenol.
Suggest Corrections
2
Join BYJU'S Learning Program
Explore more
Join BYJU'S Learning Program
