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

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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Alcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.
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