1. Carbonyl Compounds III
Chapter 19

2. Carbonyl Compounds III – ch. 19
1. Rank the following compounds in order of increasing pKa and draw the most likely enol tautomer.

3. Carbonyl Compounds III – ch. 19
2. NMR tests for the different types of hydrogen in a compound. Explain how the NMR of cyclohexanone changes after cyclohexanone is allowed to sit in a solution of basic D2O?

4. Carbonyl Compounds III – ch. 19
3. Predict the product for the following reactions.

5. Carbonyl Compounds III – ch. 19
4. Predict the product for the following reactions:

6. Carbonyl Compounds III – ch. 19
5. Predict the products for the following reactions:

7. Carbonyl Compounds III – ch. 19
6. Predict the products for the following reactions:

8. Carbonyl Compounds III – ch. 19
7. How would you prepare the following compounds from the given starting materials?

9. Carbonyl Compounds III – ch. 19
8. Predict the products for the following reactions:

10. Carbonyl Compounds III – ch. 19
9. Predict the products for the following reactions:

11. Carbonyl Compounds III – ch. 19
10. Predict the products for the following reactions:

12. Carbonyl Compounds III – ch. 19
11. Predict the product for the following reactions:

13. Carbonyl Compounds III – ch. 19
12. Predict the products for the following reactions:

14. Carbonyl Compounds III – ch. 19
13. Predict the products for the following reactions:

15. Carbonyl Compounds III – ch. 19
14. Predict the product for the following reactions:

16. Carbonyl Compounds III – ch. 19
15. Predict the product for the following reactions:

17. Carbonyl Compounds III – ch. 19
16. Predict the product for the following reaction:

18. Carbonyl Compounds III – ch. 19
17. Predict the product for the following reactions:

19. Carbonyl Compounds III – ch. 19
18. Which of the following compounds would be expected to decarboxylate when heated. Draw the decarboxylated products if applicable.

20. Carbonyl Compounds III – ch. 19
19. Predict the products for the following reactions:

21. Carbonyl Compounds III – ch. 19
20. How would you prepare the following via malonic ester synthesis?
a. 4-methylpentanoic acid
b. 3-phenylpropanoic acid

22. Carbonyl Compounds III – ch. 19
21. Predict the products for the following reactions: