MS 918 - Epoxide and Ether Practice

MS 918 - Epoxide and Ether Practice

Textbook and Chapter: Carey and Giuliano 8th Ed. (2010), Chapter 16

Keywords: epoxides, Williamson ether synthesis

Description: Covers the major topics dealing with ethers and epoxides:

  • Boiling points and water solubilities of alcohols, ethers, and carbonyls
  • Crown ethers
  • Synthesis problems involving the Williamson ether synthesis and epoxides
  • Acidic and basic ring opening of epoxides
  • Acid catalized hydrolysis of ethers
  • Total Problems: 7

    1. 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.

    2. 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.

    3. Problem # 699

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

      All carbon sources must contain three carbons or less.

    4. Problem # 700

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

    5. 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?

    6. Problem # 702

      Show how to prepare each compound starting from propylene oxide.

      (Propylene oxide image below courtesy of Wikipedia.)

    7. 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?