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 endo approach of the hydride source?

c) what would change if NaBD₄ is used as reductive reagent 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 generated in question 1 to answer this question).

c) which product would you obtain if D₂O is used in the second step?

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

a. A student decides to use acetone 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 in this reaction?

c. How do you remove the ether from the product in this experiment? Explain briefly.

d. Determine the ratio of camphor:sodium borohydride used in the reaction carried out in the lab? Rationalize this ratio.

5. Based on the thermodynamical data given in the reader (page 129/summer 2004), determine the temperature required to carry out the following reaction:

CuSO₄ * 5 H₂O ---> CuSO₄ + 5 H₂O

6. A student observes a melting point of 205-210 ^oC for his isoborneol sample. Which conclusions can he draw for this observation?