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 - Alkoxymercuration

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Making Ethers - Alkoxymercuration

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3:07 minutes

Problem 45c

Textbook Question

Show how you would synthesize the following ethers in good yield from the indicated starting materials and any additional reagents needed.
(c) 2-ethoxyoctane from an octene

Verified step by step guidance

Step 1: Recognize that the target molecule, 2-ethoxyoctane, is an ether. Ethers can be synthesized using the Williamson ether synthesis, which involves the reaction of an alkoxide ion with an alkyl halide.

Step 2: Analyze the starting material, octene. Octene is an alkene, so it must first be converted into a suitable intermediate. Perform an acid-catalyzed hydration of octene to form 2-octanol. This reaction involves the addition of water across the double bond in the presence of an acid catalyst.

Step 3: Convert 2-octanol into 2-octyl bromide (or another suitable alkyl halide) using a reagent like phosphorus tribromide (PBr₃) or thionyl chloride (SOCl₂). This step transforms the alcohol group into a good leaving group, making it reactive for the next step.

Step 4: Prepare the ethoxide ion (C₂H₅O⁻) by reacting ethanol (C₂H₅OH) with a strong base such as sodium hydride (NaH) or sodium metal (Na). This generates the nucleophilic ethoxide ion needed for the Williamson ether synthesis.

Step 5: React the 2-octyl bromide with the ethoxide ion in an SN2 reaction. The ethoxide ion will attack the carbon attached to the bromine, displacing the bromide ion and forming 2-ethoxyoctane as the final product.

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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 or alkoxides with alkyl halides through nucleophilic substitution. Understanding the mechanisms of ether formation is crucial for designing synthetic pathways, especially when aiming for specific yields and purity.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions, such as SN2 and SN1, are fundamental in organic chemistry for forming new bonds. In the context of ether synthesis, a strong nucleophile (like an alkoxide) attacks an electrophilic carbon in an alkyl halide, leading to the formation of the ether. The choice between SN2 and SN1 mechanisms depends on the structure of the substrate and the reaction conditions.

Alkenes and Their Functionalization

Alkenes are hydrocarbons with at least one carbon-carbon double bond and serve as versatile intermediates in organic synthesis. They can be functionalized through various reactions, such as hydroboration-oxidation or alkylation, to introduce new functional groups. In synthesizing ethers from alkenes, understanding how to convert the double bond into a suitable leaving group is essential for successful ether formation.

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