Chapter 5 Learning Outcomes

Learning Outcomes are summarized lists of the main ideas/skills that students should take away from a chapter. “Learning Outcomes” lists are not exhaustive; there may be other ideas/skills covered in the chapter that are also useful but not necessarily the main focus.

For Chapter 5 the Learning Outcomes are:

1. Understand the fundamentals of carbohydrates/saccharides (aldoses vs. ketoses, mono- vs. di- vs. poly-saccharides, furanose vs. pyranose, etc.).
2. Understand the fundamentals of the D/L notation system. Be able to assign D/L notation for saccharides.
3. Understand, interconvert, and draw Line-Angle, Haworth, and Fischer projections of saccharides.
4. Understand the basics of the twenty-three common monosaccharides.
5. Understand the fundamentals of epimers and the anomeric carbon (α vs. β).
6. Determine the name of a monosaccharide.
7. Understand the fundamentals of mutarotation and saccharides in equilibrium.
8. Understand and determine the name of glycosidic bonds.
9. Determine the name of a disaccharide.
10. Understand the basics of common di- and poly-saccharides.
11. Predict the major product(s), required reagents/conditions, and draw the proposed mechanisms for acid catalyzed glycoside formation of saccharides. Understand the fundamentals of the anomeric effect.
12. Predict the major product(s), required reagents/conditions, and draw the proposed mechanisms for esterification of saccharides using acid halides or anhydrides.
13. Predict the major product(s), required reagents/conditions, and draw the proposed mechanisms for alkylation of saccharides using a Lewis acid catalyst and alkyl halides.
14. Predict the major product(s), required reagents/conditions, and draw the proposed mechanisms for reduction of the carbonyl of saccharides (Alditol Synthesis).
15. Predict the major product(s), required reagents/conditions, and draw the proposed mechanisms for oxidation of the carbonyl of saccharides (Aldonic Acid Synthesis).
16. Predict the major product(s), required reagents/conditions, and draw the proposed mechanisms for oxidation of the carbonyl and primary alcohol of saccharides (Aldaric Acid Synthesis).
17. Predict the major product(s), required reagents/conditions, and draw the proposed mechanisms for chain lengthening of saccharides (Killiani-Fischer).
18. Predict the major product(s), required reagents/conditions, and draw the proposed mechanisms for chain shortening of saccharides (Wohl).