Meeting 3 Problem Set - 30BL

1.Using PC Spartan at the Science Learning Center (4 Floor Young Hall) do the following:

a. Draw camphor if you have not done it yet. Minimize the structures by clicking the minimize icon, , then save.

b. Go to the view mode by clicking the view icon, . Once in the view mode, click the Model menu and select Tube.

c. Select Calculations from the Setup menu.

The following window should appear. Select the options shown.



Verify the Charge is Neutral and Multiplicity is Singlet. Click OK.

• Select Submit from Setup menu.

  
  

  Under the Setup menu, select Surfaces. A window should appear. In this window click Add.

  

  A second window should appear. In this window, select the following

  

  Then click OK to exit dialog. Close the previous window.

  Select Submit from Setup menu. When the calculation is completed you will be notified.

  Under the Display menu, select Surfaces.

  

  A window should appear. In this window check the yellow box.

  

  Next, select the molecule by clicking on it. In the bottom right corner of the window, change the selection from Solid to Transparent.

d) Do the same (steps a-c) for 2-norbornanone.

2. Referring to the below reaction,

(endo/exo huh?)

answer the following questions:

a) which isomer is expected to be the major product for this reaction? why? (include the LUMO diagram generated in question 1 to answer this question)

b) which product results from the exo approach of the hydride source?

c) what would change if LiAlD₄ is used instead of NaBH₄ in this reaction?

3. Referring to the below reaction,

answer the following questions:

a) draw the products formed in this reaction

b) which product is the major and which is the minor? Explain using the LUMO generated above (include the diagram).

c) which product would you obtain if you would use CD₃OH as solvent?

4. Referring to the reduction of camphor answer the following questions.

a. A student decides to use diethylether instead of methanol as a solvent for the reaction. Is this a good choice?

b. Why is it important to use a minimum amount of magnesium sulfate for the drying here?

c. Why is it ill advised to boil off the diethyl ether on the hotplate?

d. how can you prevent that the solvent used in this reaction evaporates entirely during the reaction?

e. A relatively large excess of sodium borohydride is used in this reaction. Explain briefly by showing pertinent chemical equations.