Q. Identify the correct order of reactivity in electrophilic substitution reactions of the following compounds Benzene (1), Toluene (2), Chlorobenzene (3) and Nitrobenzene (4)

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Solution:

Both chloro and nitro groups are deactivating in electrophilic aromatic substitution reaction. Also nitro group is stronger deactivating group. Methyl group is activator in electrophilic aromatic substitution.
Hence, overall order of reactivity is :
nitrobenzene < chlorobenzene < benzene < toluene