# Which is more acidic - 3,5-dimethylphenol or 3,5-dimethyl-4-nitrophenol?

Does steric hinderance stops the benzene ring resonance?

• Not for phenols to my knowledge Nov 13, 2018 at 5:37
• I agree, the 4-nitrophenol will be the more acidic Nov 13, 2018 at 8:18
• But I think due to steric crowding created by two methyl groups, nitro group will go out of the plane and shouldn't take part in resonance. However it decreases the acidity by $-I$ effect , but not by $-R$ effect probably. Nov 13, 2018 at 13:11