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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)
