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For product A, draw 2 neutral products of oxymercuration and show stereochemistry.   For product B, draw the alcohol products of demercuration and include stereoisomers if any.

For product A, draw 2 neutral products of oxymercuration and show stereochemistry.   For product B, draw the alcohol products of demercuration and include stereoisomers if any.

Chemistry & Chemical Reactivity
Chemistry & Chemical Reactivity
9th Edition
ISBN:9781133949640
Author:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Chapter23: Carbon: Not Just Another Element
Section: Chapter Questions
Problem 98IL
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For product A, draw 2 neutral products of oxymercuration and show stereochemistry.

 

For product B, draw the alcohol products of demercuration and include stereoisomers if any.

Alkenes can be converted to alcohols by reaction with mercuric acetate to form a B-hydroxyalkylmercury(II) acetate compound, a reaction called oxymercuration. Subsequent reduction with NABH, reduces the C-Hg bond to a C-H bond, forming the alkyl alcohol, a reaction called demercuration. Draw the structures of the mercury-containing compound(s) and the alcohol product(s) formed in the reaction sequence, omitting byproducts. Clearly indicate stereochemistry by drawing a wedged bond, a dashed bond and two in-plane bonds per each chiral carbon. Draw hydrogen atoms that are connected to wedge-and-dash bonds. Hg(0OCCH3)2 Product(s) NABH4 Product(s) A H2O, THF HO-
Transcribed Image Text:Alkenes can be converted to alcohols by reaction with mercuric acetate to form a B-hydroxyalkylmercury(II) acetate compound, a reaction called oxymercuration. Subsequent reduction with NABH, reduces the C-Hg bond to a C-H bond, forming the alkyl alcohol, a reaction called demercuration. Draw the structures of the mercury-containing compound(s) and the alcohol product(s) formed in the reaction sequence, omitting byproducts. Clearly indicate stereochemistry by drawing a wedged bond, a dashed bond and two in-plane bonds per each chiral carbon. Draw hydrogen atoms that are connected to wedge-and-dash bonds. Hg(0OCCH3)2 Product(s) NABH4 Product(s) A H2O, THF HO-
Select all that apply: The alcohol product(s) of the reaction is characterized as being R,R. R. S. achiral. diastereomers. racemic. R,S (and/or S,R). S,S.
Transcribed Image Text:Select all that apply: The alcohol product(s) of the reaction is characterized as being R,R. R. S. achiral. diastereomers. racemic. R,S (and/or S,R). S,S.
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