Is nitrobenzene more reactive than benzoic acid for electrophilic substitution?

Question

Ryan Andrews · Accepted Answer

Probably not.....

The nitro group contains a formal positive charge, i.e. #R-stackrel(+)N(=O)O^(-)#...and when bound to a phenyl ring should deactivate the ring towards aromatic electrophilic substitution. On the other hand, the carboxyl group, should also formally deactivate the ring, given the electropositivity of the carbonyl group.... #-stackrel(delta+)C(=O)OH#

Lucy Alessi · Answer

undefined No, nitrobenzene is not more reactive than benzoic acid for electrophilic substitution. Nitrobenzene is less reactive because the nitro group (-NO2) is electron-withdrawing and deactivating, which decreases the electron density on the benzene ring, making it less susceptible to electrophilic substitution reactions. Benzoic acid, on the other hand, is more reactive because it contains a carboxylic acid group (-COOH) which can donate electrons through resonance, increasing the electron density on the benzene ring and making it more susceptible to electrophilic substitution reactions.