MS 4591 - Chem 420 Unit 6 Homework: Reaction Basics

MS 4591 - Chem 420 Unit 6 Homework: Reaction Basics

Description: Please do all the problems in 'Second Language', Chapter 8, as well as the following problem set.

Total Problems: 16

  1. Problem # 305

    Rank each group of acids in order of decreasing acidity. (1 = most acidic)

    Explain your reasoning. You will have to use more than one rule in your explanation (resonance, electronegativity, atomic radius, etc.). 

     

  2. Problem # 535
     

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

  3. Problem # 528
     

    Indicate which of the molecules below are chiral (if any).

  4. Problem # 332

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

  5. Problem # 569

    Draw all resonance forms for each species. 

    For the anion and cation species, used curved arrows. For the radical species, use hooks.

  6. Problem # 1280
     

    The structure of 2-methylbutane is shown below.

    a) Draw the structures of all possible monochloro products resulting from the free-radical chlorination of 2-methylbutane.

    b) Based on statistics alone, what do you expect the major product to be? Is this the same structure as the expected major product? Explain.

    c) How would the relative yield of the products differ if bromine was used instead of chlorine?

  7. Problem # 331

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

  8. Problem # 307

    Rank the group of molecules below in in order of decreasing basicity. (1 = most basic)

    Explain your reasoning.

  9. Problem # 1281

    Allylic and benzylic halides tend to undergo both SN1 and SN2 substitution reactions at a faster rate than their alkyl counterparts.

    For example, both allyl chloride and benzyl chloride undergo SN2 reaction at a faster rate than propyl chloride. 

    The same holds true for SN1 reactions: a 2° allyl or benzyl halide undergoes SN1 reaction faster than a 2° alkyl halide. Explain.

  10. Problem # 540

     

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

  11. Problem # 324
     

    Using curved hooks, draw a mechanism for the free radical bromination  reaction shown below.

  12. 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.

     

  13. Problem # 303

     Draw the conjugate base form of each acid listed below, then rank the acids in order or decreasing acidity (1 = most acidic).

    Explain your reasoning.

     

  14. 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.

  15. Problem # 346

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

  16. 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.