Hydroboration OxidationTable of contentsHydroboration-Oxidation is a two step pathway used to produce alcohols. The reaction proceeds in an Anti-Markovnikov manner, where the hydrogen (from BH3 or BHR2) attaches to the more substituted carbon and the boron attaches to the least substituted carbon in the alkene bouble bond. Furthermore, the borane acts as a lewis acid by accepting two electrons in its empty p orbital from an alkene that is electron rich. This process allows boron to have an electron octet. A very interesting characteristic of this process is that it does not require any activation by a catalyst. The Hydroboration mechanism has the elements of both hydrogenation and electrophilic addition and it is a stereospecific (syn addition), meaning that the hydroboration takes place on the same face of the double bond, this leads cis stereochemistry. IntroductionHydroboration-oxidation of alkenes has been a very valuable laboratory method for the stereoselectivity and regioselectivity of alkenes. An Additional feature of this reaction is that it occurs without rearrangement. The Borane ComplexFirst off it is very imporatnt to understand little bit about the structure and the properties of the borane molecule. Borane exists naturally as a very toxic gas and it exists as dimer of the general formula B2H6 (diborane). Additionally, the dimer B2H6 ignites spontaneously in air. Borane is commercially available in ether and tetrahydrofuran (THF), in these solutions the borane can exist as a lewis acid-base complex, which allows boron to have an electron octet.
The MechanismStep #1
Transition state
* Note that a carbocation is not formed. Therefore, no rearrangement takes place.
Oxidation of the Trialkylborane by Hydrogen PeroxideStep #2
Two more of these reactions with hydroperoxide will occur in order give a trialkylborate
If you need additional visuals to aid you in understanding the mechanism, click on the outside links provided here that will take you to other pages and media that are very helpful as well. Outside linksReferences
ProblemsWhat are the products of these following reactions?
#1. #2. #3.
Draw the structural formulas for the alkenes that give each alcohol upon hydroboration oxidation. #4.
#5. (E)-3-methyl-2-pentene If you need clarification or a reminder on the nomenclature of alkenes refer to the link below on naming the alkenes.
Answers #1.
#2.
#3.
#4.
#5.
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