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12. Alcohols, Ethers, Epoxides and Thiols

Making Ethers - Acid-Catalyzed Alkoxylation

12. Alcohols, Ethers, Epoxides and Thiols

Making Ethers - Acid-Catalyzed Alkoxylation

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The Mechanism of Alkoxylation.

The Mechanism of Alkoxylation.

Johnny Betancourt

Practice this topic

Textbook Question

How could the following compounds be prepared using an alkene as one of the starting materials? d.

Textbook Question

b. Which step is the rate-determining step?

Textbook Question

a. Propose a mechanism for the following reaction (show all curved arrows):

Textbook Question

What is the major product of each of the following reactions? g.

Textbook Question

How could the following compound be prepared using an alkene as one of the starting materials?

Textbook Question

Propose a mechanism for the following reaction (remember to use curved arrows to show the movement of electrons from the nucleophile to the electrophile):

Textbook Question

c. What is the electrophile in the first step? d. What is the nucleophile in the first step?

Textbook Question

e. What is the electrophile in the second step? f. What is the nucleophile in the second step?

Textbook Question

Ethers can be synthesized by substituting ethanol for water in the acid-catalyzed hydration reaction. Suggest an arrow-pushing mechanism which accounts for the formation of the ethyl ether under these conditions.

Textbook Question

Show how you would accomplish the following transformations. Some of these examples require more than one step. (a) 2-methylpropene → 2,2-dimethyloxirane (b) 1-phenylethanol → 2-phenyloxirane (c) 5-chloropent-1-ene → tetrahydropyran

Textbook Question

a. Draw the mechanism for the following reaction if it involves specific-acid catalysis.

Textbook Question

b. Draw the mechanism if it involves general-acid catalysis.

Textbook Question

Identify the alkene and alcohol partners that could be used to make the following ethers.

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Textbook Question

Draw a reaction coordinate diagram for the acid-catalyzed addition of an alcohol to an alkene. Which step is rate-determining?

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Textbook Question

a. What is the major product of each of the following reactions?

3. <IMAGE>

4. <IMAGE>

Textbook Question

How could the following compounds be prepared using an alkene as one of the starting materials?

b. <IMAGE>

Textbook Question

Show how each of the following compounds can be synthesized from an alkene:

a. <IMAGE>

Textbook Question

a. Draw the product or products that will be obtained from the reaction of cis-2-butene and trans-2-butene with each of the following reagents. If a product can exist as stereoisomers, show which stereoisomers are formed.

8. CH3OH + H2SO4

b. With which reagents do the two alkenes react to form different products?

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