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Halogenation of saturated hydrocarbons is a substitution reaction. The reaction typically involves free radical pathways. The regiochemistry of the halogenation of alkanes is largely determined by the relative weakness of the C–H bonds. This trend is reflected by the faster reaction at tertiary and secondary positions.
For example, consider radical bromination of toluene: [5] bromination of toluene with hydrobromic acid and hydrogen peroxide in water. This reaction takes place on water instead of an organic solvent and the bromine is obtained from oxidation of hydrobromic acid with hydrogen peroxide. An incandescent light bulb suffices to radicalize.
Toluene is also found in cigarette smoke and car exhaust. If not in contact with air, toluene can remain unchanged in soil or water for a long time. [39] Toluene is a common solvent, e.g. for paints, paint thinners, silicone sealants, [40] many chemical reactants, rubber, printing ink, adhesives (glues), lacquers, leather tanners, and ...
In organic chemistry, dehalogenation is a set of chemical reactions that involve the cleavage of carbon-halogen bonds; as such, it is the inverse reaction of halogenation. Dehalogenations come in many varieties, including defluorination (removal of fluorine ), dechlorination (removal of chlorine ), debromination (removal of bromine ), and ...
Regiochemistry follows from the reaction mechanism, which exhibits halogen attack on the least-hindered unsaturated carbon. The mechanism for this chain reaction resembles free radical halogenation, in which the peroxide promotes formation of the bromine radical. However, this process is restricted to addition of HBr.
In organic chemistry, an electrophilic aromatic halogenation is a type of electrophilic aromatic substitution. This organic reaction is typical of aromatic compounds and a very useful method for adding substituents to an aromatic system.
An example is the conversion of alkyl chloride into alkyl fluoride: C 3 H 5-Cl + NaF → R-F + NaCl. This kind of reaction is called Finkelstein reaction. [2] However, it is also possible, for example, to produce phosphorus fluoride compounds by transhalogenating chlorine, bromine or iodine bound to phosphorus with a metal fluoride. [3]