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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5:22 minutes

Problem 53b

Textbook Question

Oxymercuration–reduction, like acid-catalyzed hydration, can be modified to synthesize ethers. Suggest an alkene and the appropriate reaction conditions to synthesize the following ethers.
(b)

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Identify the ether to be synthesized: The given structure is an ether with a cyclohexyl group, a methyl group, and an ethyl group attached to the oxygen atom.

Determine the alkene precursor: To form the ether, consider the alkene that would lead to the desired ether upon oxymercuration-reduction. The alkene should have a double bond where the oxygen will be added.

Select the appropriate alkene: In this case, the alkene could be 1-methylcyclohexene, which has a double bond between the cyclohexyl ring and the methyl group.

Choose the reaction conditions: Oxymercuration-reduction involves two main steps. First, treat the alkene with mercuric acetate (Hg(OAc)₂) in the presence of an alcohol (in this case, ethanol) to form the mercurinium ion intermediate. Then, reduce the intermediate using sodium borohydride (NaBH₄) to form the ether.

Explain the mechanism: During oxymercuration, the alkene reacts with Hg(OAc)₂ to form a mercurinium ion. The alcohol (ethanol) attacks the more substituted carbon, leading to the formation of an ether linkage. The reduction step with NaBH₄ removes the mercury, yielding the final ether product.

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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. The first step involves the addition of mercuric acetate to the alkene, forming a mercurial intermediate. In the second step, this intermediate is reduced, typically using sodium borohydride, to yield the corresponding alcohol. This method is advantageous because it proceeds via a Markovnikov addition, ensuring that the more substituted carbon receives the hydroxyl group.

Ether Synthesis

Ethers can be synthesized through various methods, one of which involves the reaction of alcohols with alkyl halides or through the alkoxymercuration of alkenes. In the context of oxymercuration-reduction, the reaction can be modified to produce ethers by using an alcohol as a nucleophile instead of water. This results in the formation of an ether when the mercurial intermediate reacts with the alcohol, followed by reduction.

Markovnikov's Rule

Markovnikov's Rule states that in the addition of HX to an alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached, while the halide (or hydroxyl group) will attach to the more substituted carbon. This principle is crucial in predicting the outcome of reactions involving alkenes, such as oxymercuration-reduction, as it guides the regioselectivity of product formation, ensuring the desired ether structure is achieved.

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Related Practice

Textbook Question

Would you expect the following to produce an equal or unequal mixture of stereoisomers?

(c)

Textbook Question

Predict the product of each of the following alcohol synthesis reactions.

(a)

Textbook Question

In 1973, Caine and Tuller reported a synthesis of racemic oplapanone, a sesquiterpene isolated from Oplopanax japonicus (a deciduous shrub) involving a reaction we learned in this chapter. Predict the product of the reaction shown. (Caine, D.; Tuller, F. N. J. Org. Chem. 1973, 38, 3663.)

Textbook Question

Assessment 8.74 revealed that oxymercuration could be used to make cyclic esters. Suggest a likely mechanism for this transformation.

Textbook Question

The formation of five-membered ring ethers is an important goal in synthetic organic chemistry because tetrahydrofurans are contained within a number of antitumor natural products. Toward that end, a one-pot synthesis of a bis-THF containing compound was developed (Eur. J. Org. Chem. 2010, 6263–6268). Suggest a mechanism for this transformation.

Textbook Question

Show how you would synthesize each compound using methylenecyclohexane as your starting material.

(a)

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

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