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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3:29 minutes

Problem 45f

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

Verified step by step guidance

Step 1: Begin with the starting material, octan-2-ol. The hydroxyl group (-OH) on the alcohol will need to be converted into a good leaving group to facilitate the formation of the epoxide.

Step 2: Convert the hydroxyl group into a good leaving group by treating octan-2-ol with a reagent like p-toluenesulfonyl chloride (TsCl) in the presence of a base such as pyridine. This forms the tosylate derivative, which is a better leaving group.

Step 3: Perform an intramolecular Williamson ether synthesis to form the epoxide. Treat the tosylate derivative with a strong base, such as sodium hydride (NaH) or potassium tert-butoxide (KOtBu). The base will deprotonate the adjacent hydroxyl group, creating an alkoxide ion that can attack the carbon bearing the tosylate group in an SN2 reaction, forming the epoxide.

Step 4: Ensure stereochemical control to obtain the trans-2,3-epoxyoctane. The reaction conditions should favor inversion of configuration at the carbon undergoing the SN2 reaction, resulting in the trans product.

Step 5: Purify the product using techniques such as distillation or chromatography to isolate trans-2,3-epoxyoctane 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 connected to two alkyl or aryl groups. Their synthesis often involves the reaction of alcohols with dehydrating agents or through the Williamson ether synthesis, which utilizes alkoxides and alkyl halides. Understanding these methods is crucial for effectively synthesizing ethers from given starting materials.

Epoxide Formation

Epoxides are cyclic ethers with a three-membered ring structure that includes an oxygen atom. They can be synthesized from alkenes through reactions with peracids or by the intramolecular cyclization of alcohols. Recognizing how to form epoxides is essential for converting octan-2-ol into trans-2,3-epoxyoctane in the synthesis process.

Stereochemistry and Configuration

Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the case of trans-2,3-epoxyoctane, understanding the stereochemical implications of the starting material and the reaction conditions is vital for achieving the desired configuration. This knowledge helps predict the outcome of reactions and the stability of the resulting compounds.

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Related Practice

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.

(e) 1-ethoxy-1-methylcyclohexane from 2-methylcyclohexanol

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.

Multiple Choice

Predict the product of the following reaction.

Show more practices