Answer to Question #103475 in Organic Chemistry for Akshay Kumar

Question

Explain why Nitro group is meta-directing deactivator?

Answer 1

In nitrobenzene, nitro group(-NO2) is attached to the benzene ring. -NO2 group is an electron withdrawing group. It deactivates benzene ring towards electrophilic substitution reaction. Resonating structure of nitrobenzene shows +ve charge develops in ortho and para positions. As a result, the electron density at meta position is relatively higher than at the ortho and para position. So, electron deficient electrophile always attacks at meta position. Hence, nitro group is meta directing in electrophilic aromatic substitution reaction.