Draw the mechanism of the following reaction, using the curved-arrow notation to indicate the reorganization of electron density. Show all intermediates, lone pairs, nonzero formal charges, countercharges, and reversibility or irreversibility. Finally, explain in detail why the observed regio- and stereochemistry is as shown. CH3 low [:Br2] "CH3 + H-OH, :Br: excess H,0 (racemic)

Draw the mechanism of the following reaction, using the curved-arrow notation to indicate the reorganization of electron density. Show all intermediates, lone pairs, nonzero formal charges, countercharges, and reversibility or irreversibility. Finally, explain in detail why the observed regio- and stereochemistry is as shown. CH3 low [:Br2] "CH3 + H-OH, :Br: excess H,0 (racemic)

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

Chapter9: Nucleophilic Substitution And Β-elimination

Section: Chapter Questions

Problem 9.31P

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