Homework Help is Here – Start Your Trial Now!
Science
Chemistry
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

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...
See similar textbooks
icon
Related questions
icon
Concept explainers
Question
100%
OH 1. H(OAc)2, Нао 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
Transcribed Image Text:OH 1. H(OAc)2, Нао 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
OH 1. Hg(OAc)2, H2O 2. NABH4 CH3 .CH3 H2C H3C ČH3 CH3 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 +V H2C- H2C CH3 -CH3 H3C H3C (Previous Next
Transcribed Image Text:OH 1. Hg(OAc)2, H2O 2. NABH4 CH3 .CH3 H2C H3C ČH3 CH3 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 +V H2C- H2C CH3 -CH3 H3C H3C (Previous Next
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 4 images

SEE SOLUTIONCheck out a sample Q&A here
Blurred answer
Knowledge Booster
Ethers
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY
SEE MORE TEXTBOOKS