19. Reactions of Aromatics: EAS and Beyond

Rank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:

f. bromobenzene, chlorobenzene, fluorobenzene, iodobenzene

Using resonance contributors for the carbocation intermediate, explain why a phenyl group is an ortho–para director.

Predict the mononitration products of the following compounds.

a. o-nitrotoluene

b. m-chlorotoluene

c. o-bromobenzoic acid