Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

10. Addition Reactions

Oxymercuration

Organic Chemistry

10. Addition Reactions

Oxymercuration

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Problem 74c

Textbook Question

In light of your answer to Assessment 8.73, predict the product of the following oxymercuration–reduction reactions, each of which results in a single product. [Don't worry about the absolute stereochemistry, though these reactions are also stereoselective.]
(c) Oxymercuration–reduction was used in the stereoselective synthesis of the macrolactone core of neopeltolide, a marine macrolide isolated from a Caribbean sponge that has potent anticancer activity (Org. Lett. 2012, 14, 2346–2349).

Verified step by step guidance

Identify the reaction type: The reaction shown is an oxymercuration-reduction, which is used to convert alkenes to alcohols without rearrangement.

Analyze the starting material: The structure provided is a complex macrolactone with an alkene group. The alkene is the site of the oxymercuration-reduction reaction.

First step - Oxymercuration: The alkene reacts with mercuric trifluoroacetate (Hg(OTFA)2) in the presence of water. This step forms a mercurinium ion intermediate, where the mercury atom is added to the less substituted carbon of the alkene, and a hydroxyl group is added to the more substituted carbon.

Second step - Reduction: Sodium borohydride (NaBH4) is used to reduce the mercurinium ion intermediate, replacing the mercury group with a hydrogen atom, resulting in the formation of an alcohol.

Predict the product: The final product will have an alcohol group at the more substituted carbon of the original alkene, maintaining the stereochemistry of the other substituents in the macrolactone core.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Oxymercuration-Reduction

Oxymercuration-reduction is a two-step reaction used to convert alkenes into alcohols. In the first step, an alkene reacts with mercuric acetate in the presence of water, leading to the formation of a mercurial intermediate. The second step involves the reduction of this intermediate, typically using sodium borohydride, which replaces the mercury with a hydrogen atom, yielding an alcohol. This reaction is notable for its regioselectivity and stereoselectivity.

Regioselectivity

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In the context of oxymercuration-reduction, the reaction typically follows Markovnikov's rule, where the more substituted carbon atom of the alkene becomes bonded to the hydroxyl group in the final alcohol product. Understanding regioselectivity is crucial for predicting the outcome of reactions involving alkenes.

Stereoselectivity

Stereoselectivity is the property of a reaction to favor the formation of one stereoisomer over others. In oxymercuration-reduction, the reaction can lead to the formation of specific stereoisomers due to the nature of the intermediate and the subsequent reduction step. Although the question specifies not to worry about absolute stereochemistry, recognizing that the reaction can produce different stereoisomers is important for understanding the overall product distribution.

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Related Practice

Textbook Question

Show how you would accomplish the following synthetic conversions.

c. 3-methylpent-1-ene → 3-methylpentan-2-ol

Explain why acid-catalyzed hydration would be a poor choice for the reaction in (c).

Textbook Question

Predict the major products of the following reactions.

c. 4−chlorocycloheptene + Hg(OAc)₂ in CH₃OH

d. the product from part (c), treated with NaBH₄

Textbook Question

Show how you would accomplish the following synthetic conversions.

a. but-1-ene → 2-methoxybutane

b. 1-iodo-2-methylcyclopentane → 1-methylcyclopentanol

Textbook Question

In light of your answer to Assessment 8.73, predict the product of the following oxymercuration–reduction reactions, each of which results in a single product. [Don't worry about the absolute stereochemistry, though these reactions are also stereoselective.]

(b) This reaction sequence was used in the synthesis of (+) -lineatin, a monoterpene aggregation pheromone from the female ambrosia beetle Trypodendron lineatum (Org. Lett. 2004, 6, 1449–1452).

Multiple Choice

Predict the product of the following reaction.

Textbook Question

Predict the major products of the following reactions, and give the structures of any intermediates. Include stereochemistry where appropriate.

(p)

Textbook Question

Predict the major products of the following reactions.

a. 1-methylcyclohexene+ aqueous Hg(OAc)₂

b. the product from part (a), treated with NaBH₄

Textbook Question

a. Propose a mechanism for the following reaction.

b. Give the structure of the product that results when this intermediate is reduced by sodium borohydride.