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

Previous problemNext problem

2:11 minutes

Problem 51e

Textbook Question

Show how you would synthesize each compound using methylenecyclohexane as your starting material.

(e)

Verified step by step guidance

Step 1: Begin with methylenecyclohexane as the starting material. This compound contains a cyclohexane ring with a methylene group (CH2) attached via a double bond.

Step 2: Perform an electrophilic addition reaction using methanol (CH3OH) in the presence of an acid catalyst, such as H2SO4. The double bond in methylenecyclohexane will act as a nucleophile and react with the proton from the acid catalyst.

Step 3: The protonation of the double bond will generate a carbocation intermediate. Since the double bond is terminal, the carbocation will form at the more stable secondary position on the cyclohexane ring.

Step 4: Methanol (CH3OH) will act as a nucleophile and attack the carbocation, leading to the formation of a new bond between the oxygen atom of methanol and the carbon atom of the carbocation.

Step 5: Finally, deprotonation of the oxygen atom in the methanol group will occur, resulting in the formation of the desired product: cyclohexane with a methoxy group (OCH3) attached to the former double bond position.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Synthesis of Ethers

Ethers are organic compounds characterized by an oxygen atom connected to two alkyl or aryl groups. The synthesis of ethers can be achieved through various methods, including the Williamson ether synthesis, which involves the nucleophilic substitution of an alkoxide ion with a primary alkyl halide. Understanding this process is crucial for synthesizing ethers from methylenecyclohexane.

Reactivity of Alkenes

Methylenecyclohexane contains a double bond, making it an alkene. Alkenes are reactive due to the presence of the π bond, which can undergo various reactions such as electrophilic addition, oxidation, and polymerization. Recognizing the reactivity of alkenes is essential for planning synthetic routes that involve the transformation of methylenecyclohexane into other compounds.

Functional Group Transformation

Functional group transformation refers to the process of converting one functional group into another through chemical reactions. In the context of synthesizing compounds from methylenecyclohexane, understanding how to manipulate functional groups, such as converting alkenes to alcohols or ethers, is vital for achieving the desired product. This concept is foundational in organic synthesis.

Watch next

Master The Mechanism of Alkoxymercuation. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

Oxymercuration–reduction, like acid-catalyzed hydration, can be modified to synthesize ethers. Suggest an alkene and the appropriate reaction conditions to synthesize the following ethers.

(a)

Textbook Question

In light of your answer to Assessment 9.47, predict the product of the following reactions we have seen previously where an alcohol is substituted for water.

(b)

Textbook Question

Predict the product and show an arrow-pushing mechanism for the first step of the alkoxymercuration reaction.

Textbook Question

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

Textbook Question

The following cyclization has been observed in the oxymercuration-demercuration of this unsaturated alcohol. Propose a mechanism for this reaction.

Textbook Question

Show how you would make the following compounds from a suitable cyclic alkene.

(f)

Textbook Question

Oxymercuration–reduction, like acid-catalyzed hydration, can be modified to synthesize ethers. Suggest an alkene and the appropriate reaction conditions to synthesize the following ethers.

(a)

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap

Show how you would synthesize each compound using methylenecyclohexane as your starting material.(e)

Key Concepts

Synthesis of Ethers

Reactivity of Alkenes

Functional Group Transformation

Watch next

Show how you would synthesize each compound using methylenecyclohexane as your starting material.

(e)