Editing Hydroboration–oxidation reaction (section)

{{Short description|Chemical reaction that converts an alkene to an alcohol}}
'''Hydroboration–oxidation reaction''' is a two-step [[hydration reaction]] that converts an [[alkene]] into an [[Alcohol (chemistry)|alcohol]].<ref>{{cite book| author = Marc G. Loudon| year = 2002| title = Organic Chemistry| chapter = Addition Reactions of Alkenes| edition = fourth| pages = 168–172| publisher = Oxford University Press| location = New York| isbn = 0-19-511999-1}}</ref> The process results in the [[Syn and anti addition|syn addition]] of a hydrogen and a [[hydroxyl]] group where the [[double bond]] had been. Hydroboration–oxidation is an [[Markovnikov's rule|anti-Markovnikov]] reaction, with the hydroxyl group attaching to the less-substituted carbon. The reaction thus provides a more [[stereospecific]] and complementary [[regiochemistry|regiochemical]] alternative to other hydration reactions such as [[Acid catalysis|acid-catalyzed]] addition and the [[Oxymercuration reaction|oxymercuration–reduction]] process. The reaction was first reported by [[Herbert C. Brown]] in the late 1950s<ref>{{Cite journal| doi = 10.1021/ja01510a059|title = A Sterepspecific Cis Hydration of the Double Bond in Cyclic Derivatives| year = 1959| last1 = Brown | first1 = H. C.| last2 = Zweifel | first2 = G.| journal = Journal of the American Chemical Society| volume = 81| pages = 247}}</ref> and it was recognized in his receiving the [[Nobel Prize in Chemistry]] in 1979.

The general form of the reaction is as follows:
[[File:Hydroboration-oxidation reaction.png|400px|center]]

[[Tetrahydrofuran]] (THF) is the archetypal [[solvent]] used for hydroboration.