Download Chapter 1: Electronic Structure and Bonding, Acids and Bases

Chemistry 243
Chapter 21: Carbohydrates
HW: 30, 31, 35, 41, 45, 51, 54, 55, 56
Outline
I. What is a carbohydrate?
A. Terms
1. aldose, ketose
2. simple/complex carbohydrates
3. saccharides
a. mono, di, , oligo, poly
4. triose, tetrose, pentose, hexose, heptose
5. putting them together: aldotriose
B. D and L sugars
1. glyceraldehydes
C. Aldoses
1. epimers
2. mirror images (enantiomers)
D. Ketoses
II. Monosaccharide Reactions
A. epimerization
B. enediol
C. Redox rsns
1. Reduction (alditol – sugar alcohols)
2. Oxidation (Tollens test)
a. aldonic acid
b. aldaric acid
D. osazone
E. Kilaiani Fischer Synthesis (adding one carbon to the sugar as cyanide ion)
F. Wohl Degradation (remove one carbon from chain)
III. Stereochemistry
IV. Cyclic Hemiacetals
A. Haworth projections
1. amomeric carbon (α and β)
2. pyranose (5 member ring)
3. furanose (6 member ring)
4. stability of glucose
B. Converting between Fischer and Haworth projections
C. Glycosides
1. glycosidic bond
D. Reducing (and non-reducing) sugars
V. Disaccharides
A. Describing the linkage
1. α 1-4’, β1-4’, α 1-6’
VI. Polysaccharides
A. Starch (amylose and amylopectin)
B. Glycogen
C. Cellulose
VII. Sugars in nature (besides energy use/storage
A. Deoxy and amino sugars
B. Carbohydrates in cell structure
C. Artificial Sweeteners
Objectives
Knowledge
Memorize Fischer projections for glyceraldehyde, ribose, glucose
Define the terms anomeric carbon, - and -hydroxy, glycoside linkage
Define the terms mono and polysaccharride, starch, glycogen, cellulose, chiten
Familiarize yourself with the terms triose, tetrose, pentose, hexose, aldose, ketose
Define alditol, aldonic acid, aldaric acid, epimer, pyranose, furanose, reducing sugar
Comprehension
Distinguish between Haworth (ring systems) and Fischer projections (straight chains)
Understand the difference between D and L sugars
Differentiate between - and -linkages in polysaccharrides
Application
Draw disaccharrides from simple carbohydrates
Apply rxns of sugar functional groups p1012-1013 (except osazone)
Analysis
Convert sugars between Fischer and Haworth projections
Draw mechanisms for sugar rxns (except redox rxns, osazone rxn, and Wohl degradation)