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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3:44 minutes

Problem 45d

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

Verified step by step guidance

Identify the starting material and the target product. The starting material is a decene (an alkene with 10 carbon atoms), and the target product is 1-methoxydecane (an ether with a methoxy group at the first carbon).

Recognize that the synthesis of ethers can be achieved using the Williamson ether synthesis, which involves the reaction of an alkoxide ion with an alkyl halide. However, in this case, we need to first convert the decene into a suitable intermediate.

Perform a hydroboration-oxidation reaction on the decene to convert the alkene into a primary alcohol. This involves two steps: (1) Hydroboration using BH₃ or a borane reagent, and (2) Oxidation using H₂O₂ and NaOH. The product will be 1-decanol.

Convert the 1-decanol into a suitable alkyl halide, such as 1-bromodecane, by reacting it with a halogenating agent like PBr₃ or SOCl₂. This step prepares the molecule for the Williamson ether synthesis.

React the 1-bromodecane with sodium methoxide (NaOCH₃), which is a strong nucleophile. The methoxide ion will perform an SN2 substitution on the 1-bromodecane, replacing the bromine atom with a methoxy group to form 1-methoxydecane.

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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 alkenes with reagents such as alkyl halides or through methods like the Williamson ether synthesis. Understanding the reactivity of these compounds is crucial for designing effective synthetic routes.

Alkenes and Electrophilic Addition

Alkenes are hydrocarbons that contain at least one carbon-carbon double bond, making them reactive towards electrophiles. In the context of synthesizing ethers, alkenes can undergo electrophilic addition reactions to form more complex structures. Recognizing how to manipulate these reactions is essential for converting a decene into the desired ether.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group by a nucleophile. In ether synthesis, this often occurs when an alcohol acts as a nucleophile, attacking an alkyl halide. Understanding the mechanisms of these reactions, including factors that influence their rates and outcomes, is vital for achieving good yields in ether synthesis.

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Related Practice

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.

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

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.

Textbook Question

Show how you would accomplish the following synthetic conversions.

(a)

(b)

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