OH1. H(OAc)2, Нао2. NABH4CH3CH3H2CH3CAcid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H adds to the sp carbon with the mosthydrogens 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 thensubsequently reduced with sodium borohydride. This reaction proceeds through a cyclic mercurinium ion intermediate which cannot rearrange. Water adds tothe cyclic intermediate at the most substituted carbon to give an organomercury alcohol. The reduction step with sodium borohydride is complex and involvesradicalsDraw curved arrows to show the movement of electrons in this step of the mechanism.Arrow-pushing InstructionsOAcHgACOH9H2CH2C-CH3-CH3 OH1. Hg(OAc)2, H2O2. NABH4CH3.CH3H2CH3CČH3CH3Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H adds to the sp carbon with the mosthydrogens 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 thensubsequently reduced with sodium borohydride. This reaction proceeds through a cyclic mercurinium ion intermediate which cannot rearrange. Water adds tothe cyclic intermediate at the most substituted carbon to give an organomercury alcohol. The reduction step with sodium borohydride is complex and involvesradicals.Draw curved arrows to show the movement of electrons in this step of the mechanism.Arrow-pushing InstructionsOAcHgACOH9+VH2C-H2CCH3-CH3H3CH3C(PreviousNext

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ОН 1. Hо(ОАc)2. Н20 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 OAc Hg ACOH9 H2C H2C- -CH3 -CH3

ОН 1. Hо(ОАc)2. Н20 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 OAc Hg ACOH9 H2C H2C- -CH3 -CH3

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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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…
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 sp2 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…
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[Review Topics) [References) OH 1. Hg(OAc)2, H20 2. NaBH, 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 i1on 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…
CH3 CH3 Br- Br2 .CH3 CH2Cl2 CH3 H3C H3C Br Electrophilic addition of bromine, Brɔ, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl,. In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 CH3 CH3 CH3 H3C H3C :Br: :Br:
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