MS 4540 - Alcohols, Ethers, and Epoxides

MS 4540 - Alcohols, Ethers, and Epoxides

Textbook and Chapters: Brown 6th Ed. (2011), Chapters 10, 11

Keywords: alcohols, epoxides, ethers, organic chemistry

Description: Reactions of Alcohols, Ethers, and Epoxides

Total Problems: 12

  1. Problem # 347

    For the reaction below, draw the structures of the carbocation intermediate and the final product.

  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 # 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?

  4. 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?

  5. Problem # 677

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

  6. Problem # 699

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

    All carbon sources must contain three carbons or less.

  7. Problem # 700

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

  8. Problem # 702

    Show how to prepare each compound starting from propylene oxide.

    (Propylene oxide image below courtesy of Wikipedia.)

  9. Problem # 333

    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.

  10. Problem # 348

    For the reaction below, draw the structures of the carbocation intermediate and the final product.

  11. Problem # 519

    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. 

  12. Problem # 341

     Predict the product(s) of the reaction below, and used curved arrows to show a mechanism.