information:filtering, structural:reformatting
Methane radical reactions

Given appropriate conditions, methane reacts with halogen radicals as follows:

where X is a halogen: fluorine (F), chlorine (Cl), bromine (Br), or iodine (I). This mechanism for this process is called free radical halogenation. It is initiated when UV light or some other radical initiator (like peroxides) produces a halogen atom. A two-step chain reaction ensues in which the halogen atom abstracts a hydrogen atom from a methane molecule, resulting in the formation of a hydrogen halide molecule and a methyl radical (CH). The methyl radical then reacts with a molecule of the halogen to form a molecule of the halomethane, with a new halogen atom as byproduct. Similar reactions can occur on the halogenated product, leading to replacement of additional hydrogen atoms by halogen atoms with dihalomethane, trihalomethane, and ultimately, tetrahalomethane structures, depending upon reaction conditions and the halogen-to-methane ratio.

This reaction is commonly used with chlorine to produce dichloromethane and chloroform via chloromethane. Carbon tetrachloride can be made with excess chlorine.