Chapter 6.4: Hydroboration-Oxidation
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Describe the mechanism behind hydroboration-oxidation of an alkene
• Hydroboration: o Step 1: Lewis Acid-Base Coordination The addition of borane to an alkene is initiated by coordination of the vacant 2p orbital of boron with the electron pair of the pi bond o Step 2: Make a new bond between a nucleophile (pi bond) and an electrophile with simultaneous bond formation to H • Oxidation of Trialkyborane by Alkaline Hydrogen Peroxide o Step 1: Make a new bond between a nucleophile and an electrophile o Step 2: 1,2 shift o Step 3: Reaction of the trialkylborate with aqueous NaOH gives the alcohol and sodium borate
Define syn stereoselctive
the addition of atoms or groups of atoms to the same face of a carbon-carbon double bond
What is a method for converting an alkene to an alcohol. The alkene is treated with borane (BH3) to give a trialkylborane, which is then oxidized with alkaline hydrogen peroxide to give an alcohol?
hydroboration-oxidation
Define hydroboration-oxidation
a method for converting an alkene to an alcohol. The alkene is treated with borane (BH3) to give a trialkylborane, which is then oxidized with alkaline hydrogen peroxide to give an alcohol
What is the addition of atoms or groups of atoms to the same face of a carbon-carbon double bond?
syn stereoselective
What is the stereochemistry of hydroboration-oxidation?
syn
What is the regiochemistry of hydroboration-oxidation?
Non-Markovnikov