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 16b

Textbook Question

Suggest a phenoxide and an alkyl halide to make the following aryl alkyl ethers.
(b)

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Identify the ether linkage in the given structure. The structure is a 1,4-dioxane derivative with two ether linkages.

Recognize that the ether can be synthesized by the Williamson ether synthesis, which involves the reaction of a phenoxide ion with an alkyl halide.

Determine the phenoxide ion needed. In this case, the phenoxide ion would be derived from the aromatic ring with an oxygen atom attached, specifically a catechol derivative.

Identify the alkyl halide required. The alkyl halide should correspond to the alkyl chain that forms the ether linkage. Here, a 1,2-dibromoethane can be used to form the two ether linkages.

Propose the reaction: React catechol with 1,2-dibromoethane under basic conditions to form the desired aryl alkyl ether through a double Williamson ether synthesis.

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Key Concepts

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

Phenoxide Ion

A phenoxide ion is formed when a phenol loses a hydrogen ion (H+) from its hydroxyl group (-OH), resulting in a negatively charged oxygen atom. This ion is a strong nucleophile, making it highly reactive in nucleophilic substitution reactions. Understanding the stability and reactivity of phenoxide ions is crucial for predicting their behavior in ether formation.

Alkyl Halide

An alkyl halide is a compound derived from an alkane by replacing one or more hydrogen atoms with halogen atoms (such as chlorine, bromine, or iodine). These compounds are important in organic synthesis as they can undergo nucleophilic substitution reactions, where the halogen is replaced by a nucleophile, such as a phenoxide ion, to form ethers.

Williamson Ether Synthesis

Williamson ether synthesis is a method for producing ethers by reacting an alkoxide ion (derived from an alcohol) with a primary alkyl halide. This reaction typically proceeds via an SN2 mechanism, where the nucleophile attacks the electrophilic carbon of the alkyl halide, leading to the formation of an ether. Understanding this mechanism is essential for designing the synthesis of specific aryl alkyl ethers.

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Related Practice

Textbook Question

Predict the product of the following substitution/addition reactions involving phenoxides.

(a)

Textbook Question

Predict the product of the following reactions. [Two of them are Williamson ether syntheses. Why isn't the other?].

(a)

Textbook Question

Identify the alkene and alcohol partners that could be used to make the following ethers.

(a)

Textbook Question

Predict the product of the following reactions. [Two of them are Williamson ether syntheses. Why isn't the other?].

(c)

Textbook Question

Two different Williamson ether syntheses can be used to make the compound in (a). Show them. The compound in (b), however, can only be made one way. Show it and explain why a second Williamson ether synthesis is not possible.

(a)

Textbook Question

In contrast to Assessment 13.102, only one combination of haloalkane and alkoxide can be used in the Williamson ether synthesis to make the ether shown. Identify the combination and explain why it is the only combination that works.

Textbook Question

Predict the product of the following reactions. [Two of them are Williamson ether syntheses. Why isn't the other?].

(b)

Textbook Question

In Chapter 12, we learned that crown ethers were used to increase the rate of S_N2 reactions (Assessment 12.80). Suggest a synthesis of 15-crown-5 using the reactions learned here in Chapter 13.

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Suggest a phenoxide and an alkyl halide to make the following aryl alkyl ethers.(b)

Key Concepts

Phenoxide Ion

Alkyl Halide

Williamson Ether Synthesis

Watch next

Suggest a phenoxide and an alkyl halide to make the following aryl alkyl ethers.
(b)