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
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter22: Organic And Biological Molecules
Section: Chapter Questions
Problem 9Q
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Question
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).
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-
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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