Organic Chemistry II

Professor Carl C. Wamser

Chem 335 - Winter 2006

Quiz 18

1. (2 points) The dicarbonyl compound shown below could make two different enols, each of which has E,Z stereoisomers. Write all four enol structures.


2. (2 points) Complete the following reactions by adding the expected product.

a)

b)


3. (2 points) Indicate the original compound or compounds that would be used to create the following product in an aldol condensation.


4. (4 points) Write a complete mechanism for the mixed aldol condensation between benzaldehyde and acetone using NaOH.
Show all steps and all resonance forms for any intermediates involved. Abbreviate the phenyl group as C6H5 or
f .