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(OOCCH₂)2 H₂O, THF Product(s) A NaBH. HO™ Product(s) B 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.
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(OOCCH₂)2 H₂O, THF Product(s) A NaBH. HO™ Product(s) B 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.
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
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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(OOCCH3)2 Product(s)
H₂O, THF
A
Select
1. Draw 2 neutral product(s) of oxymercuration (Product A). Draw hydrogens bonded to oxygen, where applicable.
Clearly show stereochemistry.
Draw
NaBH
2. Draw the alcohol product(s) of demercuration (Product B). Include stereoisomers, if any.
Rings
HO™
11MDỀ HỌ
Product(s)
B
More
Erase](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fa0c03478-d8ba-429a-a4af-da9dd7bb9e9a%2Fe86d85b6-92d3-47d3-a671-95aee181b924%2F8qipj6i_processed.jpeg&w=3840&q=75)
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(OOCCH3)2 Product(s)
H₂O, THF
A
Select
1. Draw 2 neutral product(s) of oxymercuration (Product A). Draw hydrogens bonded to oxygen, where applicable.
Clearly show stereochemistry.
Draw
NaBH
2. Draw the alcohol product(s) of demercuration (Product B). Include stereoisomers, if any.
Rings
HO™
11MDỀ HỌ
Product(s)
B
More
Erase
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