Loudon 5th Ed. (2009)
CH 9: The Chemistry of Alkyl Halides

Solutions can be seen at mendelset.com/chapters/825


  1. Problem # 319

    For a molecule to undergo an E2 reaction, the leaving group and the beta-proton must be in an anti-coplanar conformation (one atom straight up, the other straight down). Based on this, which compound undergoes E2 reaction with KOtBu faster? Why?

     

  2. 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.

  3. Problem # 341

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

  4. Problem # 348

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

  5. 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.

  6. 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. 

  7. Problem # 531

     

    E2 elimination reactions require anti-coplanar geometry. (note: some textbooks call this anti-periplanar).
    Let's work through an E2 reaction, and rotate the molecule eblow into an anti-coplanar geometry to predict the product of this E2 reaction.

     

  8. Problem # 534

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

  9. Problem # 535

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

  10. Problem # 536

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

  11. Problem # 537

    Indicate the reagents necessary to carry out each transformation.

  12. Problem # 538

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

  13. Problem # 539

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

  14. Problem # 540

     

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

  15. Problem # 541

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

  16. Problem # 542

     

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

  17. 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)

  18. 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?