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.
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- Alkyl halides are not often found in terrestrial organisms, but the kinds of reactions they undergo are among the most important and well-studied reaction types in organic chemistry. ... Simple alkyl halides can be prepared by radical halogenation of alkanes, but mixtures of products usually result. ... Alkyl halides can also be prepared from alkenes by reaction with N-bromosuccinimide (NBS) to give the product of allylic bromination. ... Alcohols react with HX to form alkyl halides, but the reaction works well only for tertiary alcohols, R3COH. ... Alkyl halides also react with lithium metal to form organolithium reagents, RLi. In the presence of CuI, these form diorganocoppers, or Gilman reagents (LiR2Cu).
- John McMurry, Organic Chemistry 8th ed. (2012), Ch. 10. Organohalides