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For product A, draw 2 neutral products of oxymercuration and show stereochemistry.   For product B, draw the alcohol products of demercuration and include stereoisomers if any.

For product A, draw 2 neutral products of oxymercuration and show stereochemistry.   For product B, draw the alcohol products of demercuration and include stereoisomers if any.

Chemistry
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
Chapter1: Chemical Foundations
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For product A, draw 2 neutral products of oxymercuration and show stereochemistry.

 

For product B, draw the alcohol products of demercuration and include stereoisomers if any.

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 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. **Diagram Details:** 1. **Reactants and Conditions:** - Starting material: Cyclohexene. - Reactants: Hg(OOCCH₃)₂, NaBH₄. - Solvents: H₂O, THF. - Intermediate/Product(s) A: Product(s) after reaction with Hg(OOCCH₃)₂. - Product(s) B: Final alcohol product(s) after reaction with NaBH₄ and HO⁻. The diagram presents a flow from cyclohexene through two major reactions leading to different product stages labeled A and B.
Transcribed Image Text: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 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. **Diagram Details:** 1. **Reactants and Conditions:** - Starting material: Cyclohexene. - Reactants: Hg(OOCCH₃)₂, NaBH₄. - Solvents: H₂O, THF. - Intermediate/Product(s) A: Product(s) after reaction with Hg(OOCCH₃)₂. - Product(s) B: Final alcohol product(s) after reaction with NaBH₄ and HO⁻. The diagram presents a flow from cyclohexene through two major reactions leading to different product stages labeled A and B.
**Question:** Select all that apply: The alcohol product(s) of the reaction is characterized as being - [ ] R,R. - [ ] R. - [ ] S. - [ ] achiral. - [ ] diastereomers. - [ ] racemic. - [ ] R,S (and/or S,R). - [ ] S,S.
Transcribed Image Text:**Question:** Select all that apply: The alcohol product(s) of the reaction is characterized as being - [ ] R,R. - [ ] R. - [ ] S. - [ ] achiral. - [ ] diastereomers. - [ ] racemic. - [ ] R,S (and/or S,R). - [ ] S,S.
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