CHEM& 263: Organic Chemistry III

In Brief:

1. Aldehydes and Ketones revisited – nucleophilic addition to the carbonyl group
2. Carboxylic acids and their derivatives - acyl halides, acid anhydrides, esters, amides. Nucleophilic substitution at acyl carbon
3. Beta-dicarbonyl compounds – exploration of an especially reactive  position, unique properties, utility, biochemical implications
4. Aldehydes and ketones: reactions at the alpha-carbon, chemistry of enolate ions, Claisen, aldol, Michael, and Mannich reactions
5. Amines: physical and chemical properties, synthesis and reactions of amines
6. Phenols and aryl halides: nucleophilic aromatic substitution
7. Introduction to biochemistry: carbohydrates, lipids, proteins, and nucleic acids – structure and selected reactions (time permitting)

In Detail:

1. Name aldehydes and ketones using IUPAC rules
2. Establish/extend methodologies for the synthesis of aldehydes and ketones
3. Describe the formation of hemiacetals, hemiketals, acetals, and ketals, and clarify their importance in biochemistry
4. Describe imine and related carbonyl derivatives, with an emphasis on their importance in biochemistry
5. Develop and demonstrate the utility of the Wittig and Baeyer-Villiger reactions
6. Name carboxylic acids and their derivatives using IUPAC rules.
7. Propose a variety of methods for preparing carboxylic acids.
8. Write detailed reaction mechanisms for acyl transfer reactions.
9. Explain the difference in reactivity between carboxylic acid derivatives and aldehydes/ketones.
10. Explain the physical properties of carboxylic acids and their derivatives.
11. Write equations for reactions involving the synthesis and use of beta-dicarbonyl compounds, including the acetoacetic ester synthesis, the malonic ester synthesis, Knoevenagel condensations, and Michael additions.
12. Explain the formation of enolate ions.
13. Write equations for reactions that involve enolate ions.
14. Predict the products of aldol reactions.
15. Write detailed reaction mechanisms for additions to -unsaturated carbonyl compounds.
16. Name amines, using IUPAC rules.
17. Explain the basicity of amines.
18. Propose a variety of methods for the preparation of amines.
19. Write equations for a variety of reactions involving amines.
20. Explain the formation and use of arenediazonium salts.
21. Propose a variety of methods for the synthesis of phenols.
22. Explain the acidity of phenols.
23. Write equations for a variety of reactions of phenols, including nucleophilic aromatic substitution reactions.
24. Identify quinones and describe their use.
25. Distinguish between 1 and 2 electron reactions involving quinones
26. Analyze the bonding in the four major classes of biomolecules: carbohydrates, lipids, proteins, and nucleic acids.
    (Time permitting. Carbohydrates covered annually)
27. Explain the function of the four major classes of biomolecules.
    (Time permitting. Carbohydrates covered annually)
28. Explain the physical properties of the four major classes of biomolecules.
    (Time permitting. Carbohydrates covered annually)
29. Explain characteristic reactivities of the four major classes of biomolecules.
    (Time permitting. Carbohydrates covered annually)
30. Investigate selected reactions in biochemistry, particularly those solving difficult problems in organic synthesis (e.g. thiamine in decarboxylation. Time permitting)
31. Explain reports presented in the professional research literature.
32. Pose a relevant problem, design an experimental protocol for solving the problem, then carry out the protocol.
33. Synthesize a variety of organic compounds.
34. Use spectral data to analyze a variety of organic compounds.
35. Practice standard laboratory safety precautions.
36. Skillfully communicate the results of laboratory work.
37. Use chemical reference material appropriately.
38. Work effectively in groups.