12. Alcohols, Ethers, Epoxides and Thiols

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

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

(f)

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)

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)

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

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

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

(e)