Haloalkane | Wikipedia audio article
Channel: wikipedia tts
Date: 2018-12-13

This is an audio version of the Wikipedia Article:
Haloalkane


00:02:51 1 Classes
00:04:17 2 Properties
00:06:01 3 Occurrence
00:07:24 4 Nomenclature
00:07:33 4.1 IUPAC
00:08:14 5 Production
00:08:33 5.1 From alkanes
00:09:31 5.2 From alkenes and alkynes
00:10:51 5.3 From alcohols
00:12:21 5.4 From carboxylic acids
00:12:39 5.5 Biosynthesis
00:13:06 6 Reactions
00:13:34 6.1 Substitution
00:15:54 6.1.1 Mechanism
00:16:47 6.2 Elimination
00:17:39 6.3 Other
00:18:22 7 Applications
00:19:42 8 See also



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SUMMARY
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The haloalkanes (also known as halogenoalkanes or alkyl halides) are a group of chemical compounds derived from alkanes containing one or more halogens. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially and, consequently, are known under many chemical and commercial names. They are used as flame retardants, fire extinguishants, refrigerants, propellants, solvents, and pharmaceuticals. Subsequent to the widespread use in commerce, many halocarbons have also been shown to be serious pollutants and toxins. For example, the chlorofluorocarbons have been shown to lead to ozone depletion. Methyl bromide is a controversial fumigant. Only haloalkanes which contain chlorine, bromine, and iodine are a threat to the ozone layer, but fluorinated volatile haloalkanes in theory may have activity as greenhouse gases. Methyl iodide, a naturally occurring substance, however, does not have ozone-depleting properties and the United States Environmental Protection Agency has designated the compound a non-ozone layer depleter. For more information, see Halomethane. Haloalkane or alkyl halides are the compounds which have the general formula "RX" where R is an alkyl or substituted alkyl group and X is a halogen (F, Cl, Br, I).
Haloalkanes have been known for centuries. Chloroethane was produced synthetically in the 15th century. The systematic synthesis of such compounds developed in the 19th century in step with the development of organic chemistry and the understanding of the structure of alkanes. Methods were developed for the selective formation of C-halogen bonds. Especially versatile methods included the addition of halogens to alkenes, hydrohalogenation of alkenes, and the conversion of alcohols to alkyl halides. These methods are so reliable and so easily implemented that haloalkanes became cheaply available for use in industrial chemistry because the halide could be further replaced by other functional groups.
While most haloalkanes are human-produced, non-artificial-source haloalkanes do occur on Earth, mostly through enzyme-mediated synthesis by bacteria, fungi, and especially sea macroalgae (seaweeds). More than 1600 halogenated organics have been identified, with bromoalkanes being the most common haloalkanes. Brominated organics in biology range from biologically produced methyl bromide to non-alkane aromatics and unsaturates (indoles, terpenes, acetogenins, and phenols). Halogenated alkanes in land plants are more rare, but do occur, as for example the fluoroacetate produced as a toxin by at least 40 species of known plants. Specific dehalogenase enzymes in bacteria which remove halogens from haloalkanes, are also known.