Draw curved arrows to show the movement of electrons in this step of mechanism

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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Draw curved arrows to show the movement of electrons in this step of mechanism 

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
CH3
CH3
CH3
CH3
H3C
H3C
H.
H.
Transcribed Image Text: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 CH3 CH3 CH3 CH3 H3C H3C H. H.
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