Halohydrin

General structure of a halohydrin, where X = I, Br, F, or Cl

Structure of the halohydrin 2-chloroethanol

A halohydrin or a haloalcohol is a type of organic compound or functional group in which one carbon atom has a halogen substituent, and an adjacent carbon atom has a hydroxyl substituent. They are derived from alcohols are therefore characterized by the presence of both the hydroxyl functional group (-OH) and a halogen functional group. Haloalcohols, especially chloroalcohols and bromoalcohols (in which the halogen atom is chlorine or bromine, respectively) are typically synthesized by halogenation of alkenes in the presence of water or an alcohol. As intramolecular ring closure between the carbons bearing the two functional groups can be induced readily by reaction with a base to give an epoxide, haloalcohols are useful as intermediates in chemical synthesis.

Halohydrin are formed from an alkene in a halohydrin formation reaction or from an epoxide by a hydrohalic acid. In presence of a base, such as potassium hydroxide, a halohydrin may undergo internal S_N2 reaction to form an epoxide. This is the reverse of the formation reaction from an epoxide. Epoxidation in biological systems can be catalyzed by halohydrin dehalogenase.

References

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This organic chemistry article is a stub. You can help Wikipedia by expanding it.v · Categories: Functional groups Alcohol stubs Organic chemistry stubs Wikimedia Foundation. 2010. Игры ⚽ Нужна курсовая? Pope Agatho of Alexandria Agustín Díaz de Mera García Consuegra Look at other dictionaries: halohydrin — halogenhidrinas statusas T sritis chemija formulė R₂CXCR₂OH atitikmenys: angl. halohydrin rus. галогенгидрин …   Chemijos terminų aiškinamasis žodynas Halohydrin formation reaction — The halohydrin formation reaction is a chemical reaction in which a halogen is added to an alkene in aqueous solution to form a halohydrin. The reaction is a form of electrophilic addition; it is similar to the halogen addition reaction.The basic …   Wikipedia Halohydrin dehalogenase — A halohydrin dehalogenase (HheC) is an enzyme involved in the bacterial degradation of vicinal halopropanols and structurally related nematocides. In Agrobacterium Radiobacter AD1, it catalyses dehalogenation of halohydrins to produce the… …   Wikipedia halohydrin — noun Any of a class of organic compound having a hydroxyl functional group and a halogen on neighbouring carbon atoms. See Also: bromohydrin, chlorohydrin, fluorohydrin …   Wiktionary Halohydrin — Ha|lo|hy|d|rin [↑ Halogen u. ↑ hydrin], das; s, e: veraltete Bez. für org. Hydroxyverb., die in α Stellung ein Halogen Atom (X) tragen, z. B. R2C(OH) CXR2 (↑ Chlorhydrin) …   Universal-Lexikon halohydrin — hal·o·hy·drin …   English syllables halohydrin — ˈhīdrə̇n noun ( s) Etymology: International Scientific Vocabulary hal + hydrin : any of a class of organic compounds derived from glycols or polyhydroxy alcohols (as glycerol) by substitution of halogen for part of the hydroxyl groups compare… …   Useful english dictionary Alkene — This article is about the chemical compound. For the material, see Olefin fiber. Not to be confused with Alkane or Alkyne. A 3D model of ethylene, the simplest alkene. In organic chemistry, an alkene, olefin, or olefine is an unsaturated ch …   Wikipedia Darzens reaction — The Darzens reaction (also known as the Darzens condensation or glycidic ester condensation) is the chemical reaction of a ketone or aldehyde with an α haloester to form an α,β epoxy ester, also called a glycidic ester .[1][2] This reaction was… …   Wikipedia Alcohol — This article is about the generic chemistry term. For the kind of alcohol found in alcoholic beverages, see Ethanol. For beverages containing alcohol, see Alcoholic beverage. For other uses, see Alcohol (disambiguation) …   Wikipedia 18+ © Academic, 2000-2024 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”