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A hydrohalogenation reaction is the electrophilic addition of hydrogen halides like hydrogen chloride or hydrogen bromide to alkenes to yield the corresponding haloalkanes. [1] [2] [3]
For example, the chlorofluorocarbons have been shown to lead to ozone depletion. Methyl bromide is a controversial fumigant. Only haloalkanes that contain chlorine, bromine, and iodine are a threat to the ozone layer, but fluorinated volatile haloalkanes in theory may have activity as greenhouse gases.
On an industrial scale, base-promoted dehydrohalogenations as described above are disfavored. The disposal of the alkali halide salt is problematic. Instead thermally-induced dehydrohalogenations are preferred. One example is provided by the production of vinyl chloride by heating 1,2-dichloroethane: [3] CH 2 Cl-CH 2 Cl → CH 2 =CHCl + HCl
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A good example of a substitution reaction is halogenation. When chlorine gas (Cl 2) is irradiated, some of the molecules are split into two chlorine radicals (Cl•), whose free electrons are strongly nucleophilic. One of them breaks a C–H covalent bond in CH 4 and grabs the hydrogen atom to form the electrically neutral HCl.
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In reality, such a cation is not actually formed. For example, carboxylates salts are converted to ethyl esters, [6] carbanions to ethylated derivatives, thiourea into ethylisothiouronium salts, [7] and amines into ethylamines. [8]