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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7:00 minutes

Problem 118

Textbook Question

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

Verified step by step guidance

Step 1: Begin by understanding the oxymercuration reaction. Oxymercuration involves the addition of mercuric acetate (Hg(OAc)₂) to an alkene, forming a mercurinium ion intermediate.

Step 2: Analyze the structure of the starting material. The molecule contains an alkene and a hydroxyl group. The alkene is the site of the oxymercuration reaction.

Step 3: Consider the formation of the mercurinium ion. The alkene undergoes electrophilic addition with Hg(OAc)₂, forming a cyclic mercurinium ion. This intermediate is crucial for the subsequent steps.

Step 4: Examine the role of the hydroxyl group. The hydroxyl group can act as a nucleophile, attacking the mercurinium ion. This intramolecular attack leads to the formation of a cyclic ester.

Step 5: Complete the reaction with NaBH₄. Sodium borohydride (NaBH₄) is used to reduce the mercury-containing intermediate, replacing the mercury with a hydrogen atom, finalizing the formation of the cyclic ester.

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Key Concepts

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

Oxymercuration-Demercuration

Oxymercuration is a reaction that involves the addition of mercuric acetate to an alkene, forming a mercurial intermediate. This process typically leads to the formation of alcohols through nucleophilic attack by water. The subsequent demercuration step replaces the mercury with a hydrogen atom, resulting in an alcohol product. Understanding this mechanism is crucial for predicting how cyclic esters can be formed from alkenes.

Cyclic Esters (Lactones)

Cyclic esters, also known as lactones, are formed when a hydroxy acid undergoes intramolecular esterification. This process involves the reaction of a hydroxyl group with a carboxylic acid group within the same molecule, leading to the formation of a ring structure. Recognizing the conditions under which cyclic esters can form is essential for proposing a mechanism involving oxymercuration.

Mechanistic Pathways in Organic Reactions

Understanding mechanistic pathways is vital in organic chemistry as it describes the step-by-step sequence of events that occur during a chemical reaction. This includes identifying intermediates, transition states, and the role of catalysts. In the context of oxymercuration leading to cyclic esters, a clear grasp of these pathways will help in suggesting a plausible mechanism for the transformation.

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Textbook Question

Predict the product of the following aldehyde/ketone syntheses.

(d)

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

(c)

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

(a)

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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.)

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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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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.

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Textbook Question

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

(a)

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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).

591