Textbook: Wade 7th Ed. (2009)

Chapter 14: Ethers, Epoxides, and Sulfides

Practice Problems (No matching mendel sets were found.)

Individual Problems

Problem # 697

Rank the following compounds in order of decreasing boiling point.

Also, make a guess about their relative solubilities in water. Explain your reasoning.

Problem # 698

When propyl bromine is treated with KF in benzene no reaction takes place. But when the crown ether 18-Crown-6 is added to the reaction mixture the desired propyl fluoride product is produced. Explain.

Problem # 701

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?

Problem # 703

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?

Problem # 677

Show a mechanism for the acid-catalyzed cyclization (condensation) of 1,4-butanediol.

Problem # 699

Show how each compound can be prepared from the indicated starting material.

All carbon sources must contain three carbons or less.

Problem # 700

Write out a mechanism for the reaction below using curved arrows. Be sure to include formal charges. 

Problem # 702

Show how to prepare each compound starting from propylene oxide.

(Propylene oxide image below courtesy of Wikipedia.)