TOPIC: 18. Aldehydes / Ketones

SUBTOPIC: 184. Enamines

1. Write the complete mechanism of the following reaction. Show all intermediates, electron-pushing arrows and formal charges.

________________________________________________________________________

________________________________________________________________________

2. Which compound has the most nucleophilic double bond? Which has the most electrophilic double bond?

________________________________________________________________________

________________________________________________________________________

3. Show how you would accomplish the following synthetic transformation. Give all reagents and isolated products.

________________________________________________________________________

________________________________________________________________________

4. Write the complete mechanism of the following reaction. Show all intermediates, electron-pushing arrows and formal charges.

________________________________________________________________________

________________________________________________________________________

5. Draw the major product of the following reaction.

________________________________________________________________________

________________________________________________________________________

6. Draw the major product of the following reaction.

________________________________________________________________________

________________________________________________________________________

7. Draw the major product of the following reaction.

________________________________________________________________________

________________________________________________________________________

8. Perform the following synthesis using a Michael reaction.

________________________________________________________________________

________________________________________________________________________

9. Draw the major product of the following reaction.

________________________________________________________________________

________________________________________________________________________

10. Prepare the following compound starting with an enamine.

________________________________________________________________________

________________________________________________________________________

11. Prepare the following compound starting with an enamine.

________________________________________________________________________

________________________________________________________________________