Chemistry 332 - Spring 1996
Elements of Organic Chemistry II
Homework, Chapter 16 - Lipids and Nucleic Acids
McMurry, pp 504-506:
Problems 16.23-25, 31-33, 36-40, 42, 43, 47
1. Find the structure of olestra, the new synthetic fat substitute. Its
special property of being apparently undigestible is that it doesn't hydrolyze
readily, even in stomach acid. But if it did hydrolyze completely, what
products would you expect? How would this affect its nutritive value?
2. Sickle cell anemia is a genetic defect in the structure of hemoglobin,
in which just one amino acid is altered. One glutamic acid is replaced by
a valine. Describe why this change could be so serious for the protein tertiary
structure. Suggest a possible code in the DNA that might have been altered
in order to read Val instead of Glu.