Alkenes can be converted to alcohols by reaction with mercuric acetate to form a ß-hydroxyalkylmercury(II) acetate compound, a reaction called oxymercuration. Subsequent reduction with NaBH4 reduces the C-Hg bond to a C-H bond, forming the alkyl alcohol, a reaction called demercuration. Draw the structure of the Hg-containing compound and the final alcohol product formed in the reaction sequence. CH3 Hg(OOCCH3)2 NaBH4 HO™ Oxymercuration product Demercuration Product H₂O, THF Draw the alcohol product of demercuration. Draw the neutral product of oxymercuration. Omit byproducts. OH Hg Incorrect

Alkenes can be converted to alcohols by reaction with mercuric acetate to form a ß-hydroxyalkylmercury(II) acetate compound, a reaction called oxymercuration. Subsequent reduction with NaBH4 reduces the C-Hg bond to a C-H bond, forming the alkyl alcohol, a reaction called demercuration. Draw the structure of the Hg-containing compound and the final alcohol product formed in the reaction sequence. CH3 Hg(OOCCH3)2 NaBH4 HO™ Oxymercuration product Demercuration Product H₂O, THF Draw the alcohol product of demercuration. Draw the neutral product of oxymercuration. Omit byproducts. OH Hg Incorrect

Chemistry: Principles and Practice

3rd Edition

ISBN:9780534420123

Author:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward Mercer

Publisher:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward Mercer

Chapter22: Organic Chemistry And Biochemistry

Section: Chapter Questions

Problem 52QE

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Alkenes can be converted to alcohols by reaction with mercuric acetate to form a β-hydroxyalkylmercury(II) acetate compound, a reaction called oxymercuration. Subsequent reduction with NaBH4 reduces the C–Hg bond to a C–H bond, forming the alkyl alcohol, a reaction called demercuration. Draw the structures of the Hg-containing compound(s) and the final alcohol product(s) formed in the following reaction sequence, omitting byproducts. If applicable, draw hydrogen at a chirality center and indicate stereochemistry via wedge-and-dash bonds.
Briefly describe the preparation of alcohols from ketones, and the preparation of alcohols from esters, each using the same Grignard reagent CH3CH2MgCl. Show an example reaction equation involving your own chosen ketone and ester molecules,respectively, to illustrate your description
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Which alcohols can be prepared as a single product by hydroboration– oxidation of an alkene? Which alcohols can be prepared as a single product by the acid-catalyzed addition of H2O to an alkene?
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