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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4:04 minutes

Problem 61c,d

Textbook Question

What is the best way to prepare the following ethers using an alkyl halide and an alkoxide ion?
c.
d.

Verified step by step guidance

Step 1: Identify the ether structure and determine the two components needed for its synthesis: an alkyl halide and an alkoxide ion. For the first ether (cyclohexyl methyl ether), the components are cyclohexyl bromide (alkyl halide) and methoxide ion (alkoxide). For the second ether (benzyl ether), the components are benzyl bromide (alkyl halide) and phenoxide ion (alkoxide).

Step 2: Recall the Williamson Ether Synthesis mechanism, which involves the reaction of an alkoxide ion with an alkyl halide via an SN2 mechanism. This reaction works best with primary alkyl halides to avoid steric hindrance and side reactions.

Step 3: For cyclohexyl methyl ether, prepare the methoxide ion by reacting methanol (CH3OH) with a strong base like sodium hydride (NaH) or sodium metal (Na). This generates CH3O⁻, the alkoxide ion. Then, react CH3O⁻ with cyclohexyl bromide (C6H11Br) under appropriate conditions to form the ether.

Step 4: For benzyl ether, prepare the phenoxide ion by reacting phenol (C6H5OH) with a strong base like sodium hydride (NaH) or sodium metal (Na). This generates C6H5O⁻, the alkoxide ion. Then, react C6H5O⁻ with benzyl bromide (C6H5CH2Br) under appropriate conditions to form the ether.

Step 5: Ensure the reaction conditions are optimized for SN2 reactions, such as using polar aprotic solvents (e.g., DMSO or acetone) and avoiding steric hindrance in the alkyl halide. Monitor the reaction progress and purify the product using standard organic chemistry techniques like distillation or chromatography.

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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 generally formed through the reaction of an alkyl halide with an alkoxide ion, which acts as a nucleophile. Understanding the structure and properties of ethers is essential for determining the appropriate reaction conditions and reagents for their synthesis.

Alkyl Halides

Alkyl halides are organic compounds containing a carbon atom bonded to a halogen atom (such as chlorine, bromine, or iodine). They serve as electrophiles in nucleophilic substitution reactions, where the halogen is replaced by a nucleophile, such as an alkoxide ion. Recognizing the reactivity of different alkyl halides is crucial for predicting the outcome of ether synthesis.

Alkoxide Ions

Alkoxide ions are deprotonated alcohols, represented as R-O⁻, where R is an alkyl group. They are strong nucleophiles and are commonly used in the synthesis of ethers through nucleophilic substitution reactions with alkyl halides. Understanding the role of alkoxide ions in these reactions helps in selecting the right conditions for effective ether preparation.

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Related Practice

Textbook Question

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

(a)

Textbook Question

Provide the reagents necessary to carry out the following synthesis. What is the purpose of steps (a) and (e)?

Textbook Question

How could you synthesize isopropyl propyl ether, using isopropyl alcohol as the only carbon-containing reagent?

Textbook Question

Draw the product of each of the following reactions:

Textbook Question

A chemist wanted to synthesize the anesthetic 2-ethoxy-2-methylpropane. He used ethoxide ion and 2-chloro-2-methylpropane for his synthesis and ended up with no ether. What was the product of his synthesis? What reagents should he have used?

Textbook Question

Design a synthesis for each of the following, using an intramolecular reaction:

Textbook Question

The compound shown below has three different types of OH groups, all with different acidities. Show the structure produced after this compound is treated with different amounts of NaH followed by a methylating reagent. Add a brief explanation.

(a) 1 equivalent of NaH, followed by 1 equivalent of CH₃I and heat

(b) 2 equivalents of NaH, followed by 2 equivalents of CH₃I and heat

Textbook Question

Show how you would use the Williamson ether synthesis to prepare the following ethers. You may use any alcohols or phenols as your organic starting materials.

(d) ethyl n-propyl ether (two ways)

(e) benzyl tert-butyl ether (benzyl = Ph–CH₂–)

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What is the best way to prepare the following ethers using an alkyl halide and an alkoxide ion?c. d.

Key Concepts

Ethers

Alkyl Halides

Alkoxide Ions

Watch next

What is the best way to prepare the following ethers using an alkyl halide and an alkoxide ion?
c.
d.