Meeting 3 Problem Set - 30BL

1.Using PC Spartan 2002 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 diagrams generated in question 1 to answer this question. Make sure to show the proper orientation!)

b. What would change if LiAlH₄ and D₂O were used in this reaction?

c. What is the driving force for the 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 LUMO diagrams generated in question 1 to answer this question. Make sure to show the proper orientation!)

c. What would change if NaBH(OCH₃)₃ were used in this reaction?

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

a. A student uses diethylether as solvent in the reaction. What would he observe?

b. How many grams of camphor can be reduced with 0.100 g of NaBH₄? Show pertinent chemical equation and calculations.

c Why is the crude product redissolved in diethylether?

d. Why does the drying agent have to be removed before boiling off the solvent?

e. Why does the GC sample have to have a low concentration of the analyte?

f. The student observes a melting point of 175-185 ^oC for his final product. Which conclusion can he draw from this observation?

g. Outline a brief procedure how the IR spectrum is acquired for the final product.