Bruice 6th Ed. (2010)
CH 10: Reactions of Alcohols, Ethers, Epoxides, Amine, and Sulfur- Containing Compounds

Solutions can be seen at mendelset.com/chapters/1109


  1. 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.

  2. Problem # 341

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

  3. Problem # 347

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

  4. Problem # 348

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

  5. 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. 

  6. Problem # 673

    Show how each compound can be prepared from an alkene containing 3 carbons (or less).

    Each answer will involve the reaction of a Grignard with either a carbonyl or epoxide.

    Note: epoxides are prepared from alkenes using a peroxy acid (epoxidation) such as mCPBA.

  7. Problem # 677

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

  8. Problem # 678

    Draw the structure of the major organic product from each reaction sequence.

  9. Problem # 679

    Compound A (C5H12O) is oxidized using aqueous chromium (Jones reagent) to compound B (C5H10O2), which is then treated with methanol under acidic conditions to yield compound C (C6H12O2) and water.

    The 1H NMR of compound C is shown below. Determine the structures of compounds A, B, and C.

  10. 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.

  11. 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.

  12. Problem # 699

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

    All carbon sources must contain three carbons or less.

  13. Problem # 700

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

  14. 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?

  15. Problem # 702

    Show how to prepare each compound starting from propylene oxide.

    (Propylene oxide image below courtesy of Wikipedia.)

  16. 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?