Chapter 19, Problem 59P

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

a. benzene. ethylbenzene, chlorobenzene, nitrobenzene, anisole

b. l-chloro-2,4-dinitrobenzene, 2,4-dinitrophenol, l-methyl-2,4-dinitrobenzene

c. toluene, p-cresol, benzene, p-xylene

d. benzene, benzoic acid, phenol, propylbenzene

e. p-methylnitrobenzene, 2-chloro-1-methyl-4-nitrobenzene, 1-methyl-2,4-dinitrobenzene, p-chloromethlbenzene

f. bromobenzene, chlorobenzene, fluorobenzene, iodobenzene