addition reaction of chlorine to benzene
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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
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Benzene reacts with chlorine or bromine in the presence of a catalyst, replacing one of the hydrogen atoms on the ring by a chlorine or bromine atom. ... It reacts with some of the chlorine or bromine to form iron(III) chloride, FeCl3, or iron(III) bromide, FeBr3.
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