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

Making Ethers - Cumulative Practice

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Making Ethers - Cumulative Practice

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3:27 minutes

Problem 45e

Textbook Question

Show how you would synthesize the following ethers in good yield from the indicated starting materials and any additional reagents needed.
(e) 1-ethoxy-1-methylcyclohexane from 2-methylcyclohexanol

Verified step by step guidance

Step 1: Begin with the starting material, 2-methylcyclohexanol. Recognize that the hydroxyl group (-OH) on the cyclohexanol must be converted into a good leaving group to facilitate the ether synthesis.

Step 2: Convert the hydroxyl group into a better leaving group by reacting 2-methylcyclohexanol with a reagent like p-toluenesulfonyl chloride (TsCl) in the presence of a base such as pyridine. This will form the tosylate derivative, 2-methylcyclohexyl tosylate.

Step 3: Prepare the ethoxide nucleophile by reacting ethanol (C₂H₅OH) with a strong base such as sodium hydride (NaH) or sodium metal (Na). This generates sodium ethoxide (C₂H₅O⁻), a strong nucleophile.

Step 4: Perform an S_N2 reaction by reacting the 2-methylcyclohexyl tosylate with sodium ethoxide. The ethoxide ion will attack the carbon bonded to the tosylate group, displacing the tosylate and forming 1-ethoxy-1-methylcyclohexane.

Step 5: Purify the product using standard organic chemistry techniques such as distillation or chromatography to isolate 1-ethoxy-1-methylcyclohexane in good yield.

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Key Concepts

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

Ethers and Their Synthesis

Ethers are organic compounds characterized by an oxygen atom bonded to two alkyl or aryl groups. They can be synthesized through various methods, including the Williamson ether synthesis, which involves the reaction of an alkoxide ion with a primary alkyl halide. Understanding the reactivity and properties of ethers is crucial for designing effective synthetic routes.

Alcohols as Reactants

Alcohols, such as 2-methylcyclohexanol, serve as important starting materials in organic synthesis. They can undergo various transformations, including dehydration to form alkenes or nucleophilic substitution to produce ethers. Recognizing the functional groups and their reactivity patterns is essential for planning the synthesis of target compounds.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions, particularly SN2 mechanisms, are fundamental in organic chemistry for forming new bonds. In the context of ether synthesis, a nucleophile (like an alkoxide) attacks an electrophilic carbon in an alkyl halide, leading to the formation of the ether. Understanding the conditions that favor SN2 reactions, such as sterics and solvent effects, is vital for achieving good yields.

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Related Practice

Textbook Question

Show how you would accomplish the following synthetic conversions.

(a)

(b)

Textbook Question

Draw the products of the following intramolecular reactions:

Textbook Question

Draw the products of the following intramolecular reactions:

Textbook Question

The following pseudo-syntheses (guaranteed not to work) exemplify a common conceptual error.

(a) What is the conceptual error implicit in these syntheses?

(b) Propose syntheses that are more likely to succeed.

Textbook Question

Show how you would synthesize the following ethers in good yield from the indicated starting materials and any additional reagents needed.

(f) trans-2,3-epoxyoctane from octan-2-ol

Textbook Question

Show how you would synthesize the following ethers in good yield from the indicated starting materials and any additional reagents needed.

(d) 1-methoxydecane from a decene

Textbook Question

Show how you would synthesize each compound, starting with alkenes or cycloalkenes that contain no more than six carbon atoms. You may use any additional reagents you need.

(b)

Multiple Choice

Predict the product of the following reaction.

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