Resonance structure of nitro benzene
The presence of an electron withdrawing group, which has a double bond adjacent to the phenyl ring of nitrobenzene, causes the aromatic ring of nitrobenzene to have a lower electron density than that of benzene, as shown by the resonance structures of nitrobenzene.
- The phenyl ring of nitrobenzene is less nucleophilic than benzene.
- The ortho and para positions are positive in the resonance structures.
- As a result, the electrophile would react at the meta position rather than these positions in an electrophilic aromatic substitution reaction.
- When a double bond is in conjugation with the phenyl ring, it indicates that the electrophilic aromatic substitution product is the meta substituted product.