Free-radical halogenation distribution". For propane and higher alkanes, the hydrogen atoms which form part of CH (or CH) groups are preferentially replaced. The reactivity of the different halogens varies considerably. The relative rates are: fluorine (108) > chlorine (1) > bromine (7 × 10) > iodine (2 × 10). Hence, the reaction of alkanes with fluorine is difficult to control, that with chlorine is moderate to fast, that with bromine is slow and requires high levels of UV irradiation while the reaction with iodine is practically nonexistent and thermodynamically unfavorable. A common method in organic synthesis employing is the Wohl–Ziegler reaction, which
Bromine regulations (see below). Poisonous bromomethane was widely used as pesticide to fumigate soil and to fumigate housing, by the tenting method. Ethylene bromide was similarly used. These volatile organobromine compounds are all now regulated as ozone depletion agents. The Montreal Protocol on Substances that Deplete the Ozone Layer scheduled the phase out for the ozone depleting chemical by 2005, and organobromide pesticides are no longer used (in housing fumigation they have been replaced by such compounds as sulfuryl fluoride, which contain neither the chlorine or bromine organics which harm ozone). Before the Montreal protocol in 1991 (for example) an estimated