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 (Make sure that all hydrogen atooms are still attached!). 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) what would change if LiAlD₄ is used 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) what would change if CH₃OD is used in this reaction?

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

a. Why is methanol used as a solvent for the reaction? Which problems is the experimenter going to face?

b. How many moles of of NaBH₄ are required (in theory) to reduce 1.6 mmol of camphor? Show pertinent chemical equation.

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

d. Why are two products obtained in this reaction? How do they relate to each other?

e. Why should a large excess of anhydrous MgSO₄ be avoided here?

5. The IR spectrum is acquired for the final product of the reaction.

a. What are the most significant differences between the IR spectrum of camphor and the product?

b. Outline a brief procedure how the IR sample is prepared.

c. Why does the IR spectrum acquired for borneol in different in the solid and gas phase?