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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 H20, THF Но-

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 H20, THF Но-

Chemistry: The Molecular Science
Chemistry: The Molecular Science
5th Edition
ISBN:9781285199047
Author:John W. Moore, Conrad L. Stanitski
Publisher:John W. Moore, Conrad L. Stanitski
Chapter10: Fuels, Organic Chemicals, And Polymers
Section: Chapter Questions
Problem 123QRT
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1. Draw 2 neutral product(s) of oxymercuration (Product A). Draw hydrogens bonded to oxygen, where applicable. Clearly show stereochemistry.

2. Draw the alcohol product(s) of demercuration (Product B). Include stereoisomers, if any.

3. Select all the characteristics that apply to the alcohol product(s).

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 В H20, THE 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 В H20, THE HO-
Select all that apply: The alcohol product(s) of the reaction is characterized as being R,R. R. S. achiral. diastercomers. racemic. O R,S (and/or S,R). O 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. diastercomers. racemic. O R,S (and/or S,R). O S,S.
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