Question
Ortho and para nitrophenols are more acidic than phenol. Draw the resonance structures of the corresponding phenoxide ions.
Solution 1
Resonance structure of the phenoxide ion
Resonance structures of p-nitrophenoxide ion
Resonance structures of o-nitrophenoxide ion
It can be observed that the presence of nitro groups increases the stability of phenoxide ion.
Solution 2
The resonance structures of o-and p- nitrophenoxide ions and phenoxide ion are given below:
Due to -R effect of -NO2 group o- and p-nitrophenoxide are more stable than phenoxide ion. As as result, o- and p-nitrophenols are more acidic than phenol
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Solution Ortho And Para Nitrophenols Are More Acidic than Phenol. Draw the Resonance Structures of the Corresponding Phenoxide Ions. Concept: Preparation of Ethers from Dehydration of Alcohols and Williamson Systhesis.
