Chapter 24: Carbohydrates.
Learning Goals

  1. You recognize the origin of the term "carbohydrate" as "hydrate of carbon" and know how to apply this historical designation to chemical formulas.
  2. You know how to decide whether a carbohydrate is a monosaccharide, a disaccharide, a trisaccharide, an oligosaccharide or a polysaccharide.
  3. You know the major formalisms for drawing carbohydrates: the Fischer and Haworth projections. Given either of these, you can designate R and S configurations at each carbon. You can draw sawhorse projections of any structure given as a Fischer or Haworth projection.
  4. You know the difference between an aldose and a ketose, and can identify any carbohydrate as one or the other given its structure.
  5. You can assign any carbohydrate structure as D or L.
  6. Based on chemistry you remember from Ch. 18, you recognize the ability of carbohydrates to exist as cyclic hemiacetals. You recognize also that these hemiacetals may be 5-member rings (furanoses) or 6-member rings (pyranoses).
  7. You recognize that any cyclic hemiacetal form may exist as one of two diastereomers based on the configuration of the anomeric carbon.
  8. You can draw β-D glucopyranose from memory. You can draw this as a chair cyclohexane or as a Haworth projection, and you can also draw the open chain form as a Fischer projection.
  9. You can draw the chair cyclohexane, Haworth or Fischer projection of any other hexose, given its stereochemical relationship to D-glucose.
  10. You recognize the ability of a carbohydrate to engage in any of the reactions of its substituent functional groups: alcohols and aldehydes/ketones.
  11. You remember how acetals and ketals can be formed from hemiacetals or hemiketals (Ch. 18). You can apply this knowledge to glycoside formation and hydrolysis.
  12. You recognize the oxidizable functional groups in carbohydrates (alcohols, aldehydes), and you can predict based on structure whether a carbohydrate is a reducing or a nonreducing sugar.
  13. You recognize how to extend an aldose chain via the Kiliani-Fischer synthesis: form a cyanohydrin, and reduce/hydrolyze the cyano group. You recognize the stereochemical consequences of this synthesis.
  14. You know the Wohl degradation process, by which hydroxylamine converts an aldose into a cyanohydrin, which then loses HCN. You recognize the stereochemical consequences of this degradation.
  15. You recognize the philosophy behind Fischer's demonstration of carbohydrate stereochemistry.
Recommended problems: 
24.37    24.39    24.41    24.44    24.51    24.55    24.56    24.65