Chem 335 - Winter
2000Organic Chemistry II
Dr. Carl C. Wamser
Chem 335 - Winter
2000
1. (3 points) Number the carbons in 2,6-heptanedione and then apply the same numbers to identify the carbons in each of the two aldol products shown. Circle the product that you expect to be the major product.
2. (3 points) Write a complete mechanism for the base-catalyzed Claisen condensation of ethyl butanoate. Show all steps and all resonance forms for any intermediates.
3. (1 point) Show the structure of the product that would result after hydrolysis and decarboxylation of the product from question 2.
4. (3 points) Use the acetoacetic ester synthesis to prepare
4-cyclopentyl-2-butanone. Just show the sequence of steps to
be used - mechanisms and intermediate compound structures are
not required (although you may find it helpful to include some).
