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

12. Alcohols, Ethers, Epoxides and Thiols

Williamson Ether Synthesis

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Williamson Ether Synthesis

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Problem 70

Textbook Question

How could the reaction in Figure 13.67(b) be modified to produce the following ether?

Verified step by step guidance

Identify the ether product structure: The ether shown in the image is a cyclic ether with a cyclopentyl group and a branched alkyl chain.

Determine the starting materials: To form an ether, you typically need an alcohol and an alkyl halide. In this case, identify the two parts of the ether that could come from these starting materials.

Select the appropriate alcohol: The oxygen atom in the ether is typically derived from the alcohol. Here, the alcohol could be cyclopentanol, which will provide the cyclopentyl group.

Choose the alkyl halide: The remaining part of the ether, the branched alkyl chain, should come from an alkyl halide. Identify the corresponding alkyl halide that matches this structure.

Consider the reaction conditions: Use a Williamson ether synthesis, which involves the deprotonation of the alcohol to form an alkoxide ion, followed by nucleophilic substitution with the alkyl halide. Ensure the reaction conditions favor the formation of the desired ether.

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Key Concepts

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

Ethers

Ethers are organic compounds characterized by an oxygen atom bonded to two alkyl or aryl groups. They are commonly represented by the general formula R-O-R', where R and R' can be the same or different carbon chains. Understanding the structure and properties of ethers is essential for modifying reactions to synthesize them effectively.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group in a molecule by a nucleophile. In the context of ether synthesis, this often occurs through the reaction of an alcohol with an alkyl halide, where the alcohol acts as a nucleophile. Recognizing the mechanisms of these reactions is crucial for modifying conditions to achieve the desired ether product.

Reaction Conditions

The conditions under which a chemical reaction occurs, including temperature, solvent, and catalysts, significantly influence the reaction pathway and product formation. For ether synthesis, adjusting these conditions can help favor the formation of the desired ether over side products. Understanding how to manipulate these factors is key to successfully modifying the reaction.

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Related Practice

Textbook Question

A good Williamson synthesis of ethyl methyl ether would be

What is wrong with the following proposed synthesis of ethyl methyl ether? First, ethanol is treated with acid to protonate the hydroxy group (making it a good leaving group), and then sodium methoxide is added to displace water.

Textbook Question

Phenols (pK_a ≈ 10) are more acidic than other alcohols, so they are easily deprotonated by sodium hydroxide or potassium hydroxide. The anions of phenols (phenoxide ions) can be used in the Williamson ether synthesis, especially with very reactive alkylating reagents such as dimethyl sulfate. Using phenol, dimethyl sulfate, and other necessary reagents, show how you would synthesize methyl phenyl ether.

Textbook Question

Identify the two possible combinations of haloalkane and alkoxide that can be used to make the following ether.

Textbook Question

The reaction of alkoxides with haloalkanes is not a viable way to form ethers. (a) Why? (b) Why can thioethers be formed by an analogous reaction?

Textbook Question

Show how the following ethers might be synthesized using (1) alkoxymercuration– demercuration and (2) the Williamson synthesis. (When one of these methods cannot be used for the given ether, point out why it will not work.)

a. 2-methoxybutane

b. ethyl cyclohexyl ether

c. 1-methoxy-2-methylcyclopentane

Textbook Question

There are two different ways of making 2-ethoxyoctane from octan-2-ol using the Williamson ether synthesis. When pure (–)-octan-2-ol of specific rotation -8.24° is treated with sodium metal and then ethyl iodide, the product is 2-ethoxyoctane with a specific rotation of -15.6°. When pure (–)-octan-2-ol is treated with tosyl chloride and pyridine and then with sodium ethoxide, the product is also 2-ethoxyoctane. Predict the rotation of the 2-ethoxyoctane made using the tosylation/sodium ethoxide procedure, and propose a detailed mechanism to support your prediction.

Textbook Question

Propose a Williamson synthesis of 3-butoxy-1,1-dimethylcyclohexane from 3,3-dimethyl-cyclohexanol and butan-1-ol.

Textbook Question

Fluoxetine hydrochloride (Prozac®) is a widely used antidepressant. How might you stereoselectively install the indicated ether functional group (ROR) in (R)-fluoxetine?

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