formation of hexaclorobenze from benzene and excess of chlorine in dark is free radical addition reaction or free radical substitution reaction?
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In the presence of ultraviolet light (but without a catalyst present), hot benzene will also undergo an addition reaction with chlorine or bromine. The ring delocalisation is permanently broken and a chlorine or bromine atom adds on to each carbon atom.
For example, if you bubble chlorine gas through hot benzene exposed to UV light for an hour, you get 1,2,3,4,5,6-hexachlorocyclohexane or benzenehexachloride.
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