Does unsubstituted benzoic acid not show resonance due to steric effects?

Question

My book says that benzoic acid does not show resonance as the carboxylate anion and the benzene ring are not in the same plane due to steric effects. But there aren't any large groups in the ortho positions to cause steric inhibition of resonance. Then, is the info given in the book wrong? If not, where does the steric effect come from?

Answer 1

The book is inexact and misleading. The resonance is electrons moving from the ring to the carbonyl carbon, moving the carbonyl pi bond to oxygen making O- and leaving a + on the ortho carbon. Follow the resonance around and you can see why carboxylic acid directs away from ortho and para (meta director) in EAS.