Organic Chemistry III

Professor Carl C. Wamser

Chem 336 - Spring Term

Quiz 20

1.  (2 points)  Draw the structure of the compound that would have produced the following product in an aldol condensation (after dehydration).


2.  (2 points)  Draw the structure of the compound that would have produced the following product in a Claisen condensation (after hydrolysis and decarboxylation).


3.  (4 points)  Write a complete mechanism for the conjugate (1,4) addition of acetone (via its enolate anion) to 2-cyclohexenone.  Show all steps and show all resonance forms for any intermediates.


4.  (2 points)  Show the reaction sequence that would prepare pentanoic acid via a malonic ester synthesis.