Brown 6th Ed. (2011)
CH 6: Reactions of Alkenes

Solutions can be seen at mendelset.com/chapters/1163


  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 # 336

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

  9. Problem # 337

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

  10. Problem # 342

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

     

  11. Problem # 343

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

  12. Problem # 344

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

  13. Problem # 345

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

     

  14. Problem # 347

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

  15. 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.

  16. Problem # 520

    Let's work through an alkene addition reaction. Draw the structures for each of the species in the three boxes below (3º carbocation, protonated thiol, and thiol). Also draw curved arrows to show electron movement. Note: thiol = RSH, like an alcohol, but with sulfur instead of oxygen.

     

  17. Problem # 521

    Let's work through a halogenation reaction. Draw the structures for each of the species in the four boxes below (3º carbocation, halonium ion, protonated thiol, and thiol). Also draw curved arrows to show electron movement. Note: thiol = RSH, like an alcohol, but with sulfur instead of oxygen.

  18. Problem # 529

    Indicate the major organic product of the reaction below. Include stereochemistry.

  19. Problem # 530

     

    Let's work through anti and syn additions to alkenes.
    Show the product for each reaction below, and indicate whether the product will be a racemic mixture of enantiomers, or a meso compound (which is achiral).

  20. Problem # 1336

    Determine a synthesis to prepare 2-chloro-4-methylpentane from 1-iodo-4-methylpentane.

     

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