Description: Reactions of Alcohols, Ethers, and Epoxides
Total Problems: 12
For the reaction below, draw the structures of the carbocation intermediate and the final product.
Rank the following compounds in order of decreasing boiling point.
Also, make a guess about their relative solubilities in water. Explain your reasoning.
The acid-catalyzed condensation of alcohols to form ethers is reversable; ethers can be hydrolyzed back to alcohols. How can the direction of this equilibrium be controlled to preferentially form ethers?
Show two ways to prepare the ether below from a combination of an alcohol and an alkyl halide via the Williamson ether synthesis.
Is one way better than the other? Why?
Show a mechanism for the acid-catalyzed cyclization (condensation) of 1,4-butanediol.
Show how each compound can be prepared from the indicated starting material.
All carbon sources must contain three carbons or less.
Write out a mechanism for the reaction below using curved arrows. Be sure to include formal charges.
Show how to prepare each compound starting from propylene oxide.
(Propylene oxide image below courtesy of Wikipedia.)
Let's go over how a carbocation can form from an alcohol.
Write in the curved arrows to show the formation of the protonated alcohol, and water acting as a leaving group to form a carbocation.
For the reaction below, draw the structures of the carbocation intermediate and the final product.
Let's work through an elimination reaction. Draw the structures for each of the species in the three boxes below (protonated thiol, carbocation, and alkene). Also draw curved arrows to show electron movement.
Predict the product(s) of the reaction below, and used curved arrows to show a mechanism.