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OH 1. Hg(OAc)2, H2O 2. NABH4 .CH3 CH3 H2C H3C Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H* adds to the sp car hydrogens to yield the most stable carbocation intermediate, which then adds water to give the product alcohol. Because a carbocation inte rearrangements can occur prior to the addition of water. To avoid the possibility of rearrangement and still give a Markovnikov alcohol, alkenes can instead be treated with mercury(II) acetate in a subsequently reduced with sodium borohydride. This reaction proceeds through a cyclic mercurinium ion intermediate which cannot rearra the cyclic intermediate at the most substituted carbon to give an organomercury alcohol. The reduction step with sodium borohydride is co: radicals. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions + Aco-Hg-OAc AcO-Hg OAc

OH 1. Hg(OAc)2, H2O 2. NABH4 .CH3 CH3 H2C H3C Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H* adds to the sp car hydrogens to yield the most stable carbocation intermediate, which then adds water to give the product alcohol. Because a carbocation inte rearrangements can occur prior to the addition of water. To avoid the possibility of rearrangement and still give a Markovnikov alcohol, alkenes can instead be treated with mercury(II) acetate in a subsequently reduced with sodium borohydride. This reaction proceeds through a cyclic mercurinium ion intermediate which cannot rearra the cyclic intermediate at the most substituted carbon to give an organomercury alcohol. The reduction step with sodium borohydride is co: radicals. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions + Aco-Hg-OAc AcO-Hg OAc

Chemistry
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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ОН 1. H(OAc)2, На0 2. NABH4 .CH3 CH3 H2C H3C Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H adds to the sp carbon with the most hydrogens to yield the most stable carbocation 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. To avoid 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 sodium borohydride. 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 organomercury alcohol. The reduction step with sodium borohydride is complex and involves radicals. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions AcO-Hg-OAc AcO-Hg OAc
Transcribed Image Text:ОН 1. H(OAc)2, На0 2. NABH4 .CH3 CH3 H2C H3C Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H adds to the sp carbon with the most hydrogens to yield the most stable carbocation 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. To avoid 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 sodium borohydride. 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 organomercury alcohol. The reduction step with sodium borohydride is complex and involves radicals. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions AcO-Hg-OAc AcO-Hg OAc
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