MendelSet


MS 904 - Carbocation Drills

Solutions can be seen at mendelset.com/ms/904

Submitted by Matt on August 6, 2011

Description: This mendel set guides you through everything you have to know about carbocations:

  • Ways carbocations form
  • Carbocation rearrangements
  • How carbocations react (elimination or nucleophilic attack)

Also includes some practice problems: addition to an alkene, dehydration (E1), and substitution (SN1).

Total Problems: 8


  1. Problem # 331

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

  2. Problem # 332

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

  3. 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.

  4. 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.

     

  5. 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.

  6. Problem # 336

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

  7. Problem # 337

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

  8. Problem # 341

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