Wade 7th Ed. (2009)
CH 6: Alkyl Halides: Nucleophilic Substitution and Elimination

Solutions can be seen at mendelset.com/chapters/1024


  1. Problem # 321

    Using curved arrows, draw a mechanism for the SN1 reaction shown below.

     

  2. Problem # 322

    Using curved arrows, draw a mechanism for the SN1 reaction shown below.

  3. Problem # 331

    Rank the carbocations below in order of decreasing stability. (1 = most stable)

  4. Problem # 332

    Each of the carbocations below will spontaneously rearrange. Draw the structure of the expected rearrangement product.

  5. 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.

  6. Problem # 334

     Let's go over how a carbocation can form from an alkene.

    Use curved arrows to show the two carbocations that can from from 1-methylcyclohexene.

     

  7. Problem # 335

    Carbocations aren't very stable and so don't last very long after they are formed.

    Use curved arrows to show:

    a) how a carbocation reacts with a halide ions to form an alkyl halide.

    b) how a carbocation reacts with water to form an alcohol.

    c) how a carbocation reacts with a base to form an alkene.

  8. Problem # 337

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

  9. Problem # 347

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

  10. Problem # 348

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

  11. Problem # 518

    The alcohol below is protonated and contains an oxygen with a positive charge. Using curved arrows, show the two "legal moves" that result in a neutral oxygen.

  12. Problem # 534

    Using curved arrows, draw the mechanism for the SN2 reaction below.

  13. Problem # 535

    Rank the following anions in order of decreasing stability (1 = most stable)

  14. Problem # 536

    Rank the following electrophiles in order of decreasing reactivity with NaN3 in DMF. (1 = most reactive)

  15. Problem # 537

    Indicate the reagents necessary to carry out each transformation.

  16. Problem # 538

    Rank the following electrophiles in order of decreasing reactivity with NaN3 in DMF. (1 = most reactive)

  17. Problem # 539

    Rank the following compounds in order of decreasing nucleophilicity. (1 = most nucleophilic)

  18. Problem # 540

     

    Rank the following anions in order of decreasing stability (1 = most stable)

  19. Problem # 541

    Rank the following compounds in order of decreasing reactivity with NaI in acetone. (1 = most reactive)

  20. Problem # 542

     

    Rank the following compounds in order of decreasing reactivity with water (solvolysis). (1 = most reactive)

  21. Problem # 560

    For each reaction below, determine whether the primary reaction is SN1, SN2, E1, or E2, and then draw the product.

    Note: Me = methyl (CH3)

  22. 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?