Bruice 6th Ed. (2010)
CH 8: Substitution Reactions of Alkyl Halides

Solutions can be seen at mendelset.com/chapters/1107


  1. Problem # 348

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

  2. Problem # 534

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

  3. Problem # 535

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

  4. Problem # 536

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

  5. Problem # 537

    Indicate the reagents necessary to carry out each transformation.

  6. Problem # 538

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

  7. Problem # 539

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

  8. Problem # 540

     

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

  9. Problem # 541

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

  10. Problem # 542

     

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

  11. 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)

  12. 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?