OH 1. Hg(OAc)2, H2O 2. NABH4 CH3 .CH3 H2C° H3C d-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H¯ adds to the sp² carbon with the most hydrogens to yield the most stab ocation intermediate, which then adds water to give the product alcohol. Because a carbocation intermediate is formed, rearrangements can occur prior to the addition of water. void the possibility of rearrangement and still give a Markovnikov alcohol, alkenes can instead be treated with mercury(II) acetate in aqueous THF and then subsequently reduced with se phydride. This reaction proceeds through a cyclic mercurinium ion intermediate which cannot rearrange. Water adds to the cyclic intermediate at the most substituted carbon to give an anomercury alcohol. The reduction step with sodium borohydride is complex and involves radicals. w curved arrows to show the movement of electrons in this step of the mechanism. row-pushing Instructions AcO-Hg-OAc AcO-Hg OAC

OH 1. Hg(OAc)2, H2O 2. NABH4 CH3 .CH3 H2C° H3C d-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H¯ adds to the sp² carbon with the most hydrogens to yield the most stab ocation intermediate, which then adds water to give the product alcohol. Because a carbocation intermediate is formed, rearrangements can occur prior to the addition of water. void the possibility of rearrangement and still give a Markovnikov alcohol, alkenes can instead be treated with mercury(II) acetate in aqueous THF and then subsequently reduced with se phydride. This reaction proceeds through a cyclic mercurinium ion intermediate which cannot rearrange. Water adds to the cyclic intermediate at the most substituted carbon to give an anomercury alcohol. The reduction step with sodium borohydride is complex and involves radicals. w curved arrows to show the movement of electrons in this step of the mechanism. row-pushing Instructions AcO-Hg-OAc AcO-Hg OAC

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter10: Alcohols

Section: Chapter Questions

Problem 10.52P: Alcohols are important for organic synthesis, especially in situations involving alkenes. The...

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