Chemistry · Ch 11 — Hydroxy Compounds and Ethers
Preparation of Alcohols by Hydroboration-Oxidation
11.3.4
Preparation of Alcohols by Hydroboration-Oxidation
Diborane (B2H6) adds across an alkene's double bond to form a trialkylborane, which on treatment with alkaline hydrogen peroxide (H2O2/NaOH) gives an alcohol; overall this is a hydration of the alkene that follows the ANTI-Markovnikov rule, placing the -OH on the LESS substituted carbon. For example, six moles of propene react with B2H6 to give tripropylborane, (CH3-CH2-CH2)3B, which with H2O2/OH- gives propan-1-ol plus boric acid, B(OH)3 …