1. Review IR spectra at http://chipo.chem.uic.edu/web1/ocol/spec/IR.htm

2. Review NMR spectra at http://chipo.chem.uic.edu/web1/ocol/spec/NMR.htm

3. Give 5 structures that are considered aromatic.

4. Draw structures for (a) phenol; (b) m-bromotoluene; (c) 4-methyl-2-nitrobenzaldehyde.

5. Write the mechanism for the nitration of benzene.

6. Write the structure and name for the  major product obtained when toluene is reacted with nitric and sulfuric acid acids in the presence of heat.

7. When bromine reacts with benzene do you get the same product in the absence of ultraviolet light as you do when UV is present? Explain.

8. Name the following: (a) (CH3)2CH-CH2-C(H)=O; (b)(CH3)2-C(=O)-CH2-CH3

9. List 2 ways to synthesize alehydes and include an example for each.

10. List 4 ways to make ketones (include examples).

11. List 6 reactions aldehydes/ketones undergo (include examples).

12. Name the following carboxylic acid: CH3-CH2-CH(CH3)-C(=O)OH

13. List 4 ways to make carboxylic acids (include examples).

14. List 3 reactions carboxylic acids undergo (include examples).

15. Draw structures for the following: (a) propanoyl chloride; (b) ethanoic anhydride; (c) N-methyl ethanamide; (d) methyl butanoate; (e) butanenitrile

16. Carboxylic acid derivatives tend to undergo a certain type of reaction. Give a mechanistic example of this reaction type.

17. List 4 reactions of acid halides (include examples).

18. List 3 reactions of anhydrides (include examples).

19. List 4 reactions of esters (include examples).

20. List 3 ways to prepare amides (include examples).

21. List 2 reactions of amides and 2 reactions of nitriles (include examples).

22. Synthesize pentanoic acid via malonate ester synthesis.

23. Synthesize 3-methyl-2-pentanone via acetoacetic ester synthesis.

24. Synthesize 3-hydroxy-2,2,4-trimethylpentanal via aldol synthesis.

25. Synthesize methyl 2-methyl-3-oxo-3-phenylpropanoate via crossed Claisen.

26. Write the structure for diisopropylamine.

27. Using the Gabriel reaction synthesize 1-aminopropane (n-propylamine).

28. List 4 reactions used to prepare amines (include examples).

29. Draw the structure for furo[3,4-b]pyrrole.

30. What is medicinal chemistry?