1. Chapter 18: Carbohydrates
Chem 330, Chapter 18 Carbohydrates
Chapter 18: Carbohydrates
glucose
Copyright 2002, David R. Anderson

2. Monosaccharides
Classification
Stereoisomers
Fischer projections
D- and L-sugars
Cyclic structures
cyclic hemiacetals
Haworth projections and chair conformations
mutarotation
Reactions
glycosides (acetals)
reduction
oxidation
Disaccharides and Oligosaccharides
Polysaccharides

3. I. Monosaccharides
A. Classification

4. I. Monosaccharides
A. Classification

5. I. Monosaccharides
B. Stereoisomers
1. Fischer projections

6. I. Monosaccharides
B. Stereoisomers
2. D- and L-sugars

7. I. Monosaccharides
B. Stereoisomers
2. D- and L-sugars

8. I. Monosaccharides B. Stereoisomers 2. D- and L-sugars
aldopentoses: 3 chiral carbons, 8 stereoisomers (4 D & 4 L)
aldohexoses: 4 chiral carbons, 16 stereoisomers (8 D & 8 L)

9. I. Monosaccharides
B. Stereoisomers
2. D- and L-sugars

10. I. Monosaccharides
C. Cyclic structures
1. cyclic hemiacetals

11. I. Monosaccharides C. Cyclic structures
1. Haworth projections and mutarotation

12. I. Monosaccharides C. Cyclic structures
1. Haworth projections and mutarotation

13. I. Monosaccharides
C. Cyclic structures
2. chair conformations

14. Practice Exercises
Draw the Haworth and chair structures of b-D-galactopyranose.
What sugar is shown in the following structure? Name the structure.

15. I. Monosaccharides
D. Reactions
1. glycosides (acetals)

16. I. Monosaccharides
D. Reactions
2. reduction to alditols

17. I. Monosaccharides D. Reactions
2. oxidation to aldonic and aldaric acids

18. I. Monosaccharides D. Reactions
2. oxidation to aldonic and aldaric acids
Reducing sugars: reduce Benedict’s solution (Cu+2  Cu2O)

19. II. Disaccharides

20. II. Disaccharides

21. Practice Exercises
What two monosaccharides comprise lactose? What is its full name?

22. II. Disaccharides
Reducing sugars: free hemiacetal (always in equilibrium with open chain aldehyde)

23. II. Polysaccharides