Organic Chemistry II

Professor Carl C. Wamser

Chem 335 - Winter 2008

Quiz 18

1. (3 points) Write the structure of the enolate (both resonance forms) expected to be formed when LDA reacts with 2-methylcyclohexanone. Write the structure of LDA.


2. (2 points) Complete each of the following two reactions:

a)

b)


3. (2 points) Draw the structures of the two compounds that would have reacted in an aldol condensation (with dehydration) to form the product shown below.


4. (3 points) Write a complete mechanism for the aldol condensation (with dehydration) of the generic aldehyde shown below. Show all steps and show all resonance forms for any intermediates.