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General structure of a halohydrin, where X = I, Br, F, or Cl Structure of the halohydrin 2-chloroethanol. In organic chemistry a halohydrin (also a haloalcohol or β-halo alcohol) is a functional group in which a halogen and a hydroxyl are bonded to adjacent carbon atoms, which otherwise bear only hydrogen or hydrocarbyl groups (e.g. 2-chloroethanol, 3-chloropropane-1,2-diol). [1]
A specific example is a halohydrin formation reaction with 2-propenylbenzene: [3] Because of the preference for the formation of one product over another, the reaction is selective. This reaction is regioselective because it selectively generates one constitutional isomer rather than the other.
Halohydrin formation reaction; Hammick reaction; Hammond principle or Hammond postulate; Hantzsch pyrrole synthesis; Hantzsch dihydropyridine synthesis, Hantzsch pyridine synthesis; Hantzsch pyridine synthesis, Gattermann–Skita synthesis, Guareschi–Thorpe condensation, Knoevenagel–Fries modification; Hantzsch–Collidin synthesis; Harries ...
The first part of the reaction mechanism consists of an ordinary nucleophilic aliphatic substitution to produce a gem-halohydrin: . RCH(Cl) 2 + KOH RCH(OH)Cl + KCl. The remaining halide is a good leaving group and this enables the newly created hydroxy group to convert into a carbonyl group by expelling the halide:
This page was last edited on 7 October 2015, at 10:55 (UTC).; Text is available under the Creative Commons Attribution-ShareAlike 4.0 License; additional terms may ...
For example, HOCl can react with double bonds in the organic reactant or product via a halohydrin formation reaction. To prevent interference from HOCl, a scavenger is usually added to the reaction to consume the HOCl as it is formed. For example, one can take advantage of the propensity of HOCl to undergo this addition reaction by adding a ...
Formation of a secondary alcohol via alkene reduction and hydration is shown: The hydroboration-oxidation and oxymercuration-reduction of alkenes are more reliable in organic synthesis. Alkenes react with N-bromosuccinimide and water in halohydrin formation reaction. Amines can be converted to diazonium salts, which are then hydrolyzed.
These halohydrin species can be cyclized to the corresponding tetrahydropyran derivates under basic conditions. [20] Large excesses of activated alkenes can be used to intercept the alkyl radical and results in formation of a C-C bond from an unactivated C-H bond. [21]