Chem 336 - Spring 2002
Organic Chemistry III
Dr. Carl C. Wamser
1. (2 pts) Write all the resonance forms for the most stable anion formed from malonic ester and sodium ethoxide.
2. (4 pts) Complete the following reactions by adding the missing part: either the starting compound, the necessary reagents and conditions, or the expected major product.
a) 
b) 
3. (4 pts) It is possible to modify the acetoacetic ester synthesis to make ketones of the general substitution pattern shown below. The synthesis starts by carrying out a Claisen condensation with the ester shown below, and then using that product for the rest of the steps usually performed in an acetoacetic ester synthesis.
Illustrate the steps that would be needed to make the specific ketone shown.
