text: Generally, two kinds of reactions occur with xylenes: those involving the methyl groups and those involving the ring C–H bonds.  Being benzylic and hence weakened, the C–H bonds of the methyl groups are susceptible to free-radical reactions, including halogenation to the corresponding xylene dichlorides (bis(chloromethyl)benzenes), while mono-bromination yields xylyl bromide, a tear gas agent. Oxidation and ammoxidation also target the methyl groups, affording dicarboxylic acids and the dinitriles. Electrophiles attack the aromatic ring, leading to chloro- and nitroxylenes.