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? 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 is "D" anyway?

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 NaAlD₄ and CD₃OD as reagents?

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

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

b. Why is magnesium sulfate is added to the mixture during the work-up? Why is it important to use a minimum amount?

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

d. referring to the vacuum filtration performed in this experiment, draw a sketch of the setup. Label all parts.

5. How could you prove that a racemic mixture of isoborneol is obtained in this experiment?

6. A student isolates a white powder from his reaction. He determines the melting point to be 130-132 ^oC. Which conclusion can he draw from this observation?