Organochloride

An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound containing at least one covalently bonded atom of chlorine that has an effect on the chemical behavior of the molecule. The chloroalkane class (alkanes with one or more hydrogens substituted by chlorine) provides common examples. The wide structural variety and divergent chemical properties of organochlorides lead to a broad range of names and applications. Organochlorides are very useful compounds in many applications, but some are of profound environmental concern. An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound containing at least one covalently bonded atom of chlorine that has an effect on the chemical behavior of the molecule. The chloroalkane class (alkanes with one or more hydrogens substituted by chlorine) provides common examples. The wide structural variety and divergent chemical properties of organochlorides lead to a broad range of names and applications. Organochlorides are very useful compounds in many applications, but some are of profound environmental concern. Chlorination modifies the physical properties of hydrocarbons in several ways. The compounds are typically denser than water due to the higher atomic weight of chlorine versus hydrogen. Aliphatic organochlorides are alkylating agents because chloride is a leaving group. Many organochlorine compounds have been isolated from natural sources ranging from bacteria to humans. Chlorinated organic compounds are found in nearly every class of biomolecules including alkaloids, terpenes, amino acids, flavonoids, steroids, and fatty acids. Organochlorides, including dioxins, are produced in the high temperature environment of forest fires, and dioxins have been found in the preserved ashes of lightning-ignited fires that predate synthetic dioxins. In addition, a variety of simple chlorinated hydrocarbons including dichloromethane, chloroform, and carbon tetrachloride have been isolated from marine algae. A majority of the chloromethane in the environment is produced naturally by biological decomposition, forest fires, and volcanoes. The natural organochloride epibatidine, an alkaloid isolated from tree frogs, has potent analgesic effects and has stimulated research into new pain medication. However, because of its unacceptable therapeutic index, it is no longer being researched for potential therapeutic uses.The frogs obtain epibatidine through their diet and then sequester it on their skin. Likely dietary sources are beetles, ants, mites, and flies. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst. The haloform reaction, using chlorine and sodium hydroxide, is also able to generate alkyl halides from methyl ketones, and related compounds. Chloroform was formerly produced thus.