4-HydrationAlkenesF07

4-HydrationAlkenesF07 - 3. Addition of HOH to an Alkene...

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Unformatted text preview: 3. Addition of HOH to an Alkene (alkenes to alcohols) Three Methods A. Hydration (4.9B) B. Oxymercuration/Reduction (5.3A) C. Hydroboration/Oxidation (5.3B) 3A) Acid-catalyzed hydration : E+ = H3O+ OH H O H Mechanism CH3 H excess H O H O 5% H O S O H O Regioselectivity: Relative Reactivity of Alkenes - Which reaction is faster? H3C H3C H3C H H H H H H H H O CH3 H H H3C OHH CH3 H H H OHH H H H O Application/Extension OH 5% H2SO4 3B. Oxymercuration/Reduction of Alkene (Section 5.3A) OH HgOAc HOH AcOHgOAc THF mercuric acetate Oxymercuration Reduction NaBH4 OH H Mechanism of Oxymercuration AcO Hg OAc Pr Regioselectivity: Competing Transition States 3C. Hydroboration/Oxidation 1. BH3 2. H2O2, H2O, NaOH OH H H.C. Brown Nobel Prize 1979 Borane in a bottle: Regioselectivity: Hydroboration BH3 BH2 H Organoborane H 3 B 3 Trialkylborane Oxidation B H 3 H2O2 NaOH H2O H OH + NaB(OH)4 Trialkylborane Mechanism of Hydroboration BH3 CH3 Predict products - which is major regioisomer? CH3 H3C H H CH3 1. BH3 2. H2O2, H2O NaOH How might you improve regioselectivity? ...
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This note was uploaded on 05/13/2010 for the course CHEM 151L taught by Professor Roy,christopher during the Fall '08 term at Duke.

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4-HydrationAlkenesF07 - 3. Addition of HOH to an Alkene...

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