Chlorinated Benzenes

Although benzene does not readily undergo addition reactions with molecules or ions that are not free radicals, it does participate in substitution reactions: One of its hydrogen atoms can be replaced by a group such as methyl, hydroxyl, etc., that forms a single bond. Of particular interest is substitution by chlorine, since many compounds of environmental concern contain chlorine-substituted benzene rings. When benzene is reacted with chlorine gas in the presence of a catalyst such as iron(III) chloride, FeCl5, one of the hydrogens (explicitly drawn on the ring below for clarity) is replaced by chlorine, and HCl gas is released:

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