Brown 6th Ed. (2011)
CH 11: Ethers, Sulfides, and Epoxides

Solutions can be seen at

  1. Problem # 677

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

  2. 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.

  3. 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.

  4. Problem # 699

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

    All carbon sources must contain three carbons or less.

  5. Problem # 700

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

  6. 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?

  7. Problem # 702

    Show how to prepare each compound starting from propylene oxide.

    (Propylene oxide image below courtesy of Wikipedia.)

  8. 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?