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 & Chemical Reactivity

10th Edition

ISBN:9781337399074

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 106IL

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