Pericyclic Reactions

January 14, 2015

*For all problems, please name the reaction, classify the type of pericyclic reaction, and draw the
relevant molecular orbitals.

1. Compare the mechanism of thermal vs. copper catalyzed Huisgen reactions- what are some of the
benefits of the catalyzed reaction?

2. Predict the product of the top reaction, and explain the regioselectivity of the pi bond in both
products.

3. Explain the exo:endo preference displayed in this reaction. Could any of the products rearrange upon
further heating?

4. Identify the compound formed following Step 2 and propose a feasible route to form the product.
5. The authors found that there was a linear relationship between the ee of the catalyst and that of the
product- what does this mean for the reaction mechanism?

6. Draw the compound formed after step 1.

7. Explain the stereoselectivity of the following reaction: