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

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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