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12. Alcohols, Ethers, Epoxides and Thiols

Making Ethers - Alkoxymercuration

12. Alcohols, Ethers, Epoxides and Thiols

Making Ethers - Alkoxymercuration

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The Mechanism of Alkoxymercuation.

The Mechanism of Alkoxymercuation.

Johnny Betancourt

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Textbook Question

a. 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)

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.

(c) 2-ethoxyoctane from an octene

Textbook Question

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

e. <IMAGE>

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