Chemistry 332 - Spring 1996
Elements of Organic Chemistry II
Homework, Chapter 14 - Carbohydrates
McMurry, pp 439-441:
Problems 14.24, 25, 28, 31, 33, 36, 37, 39, 42, 44
1. Construct a family tree for the D-ketoses up to the D-ketopentoses. Your
diagram should be patterned after the one shown in your text for the D-aldoses
(page 418).
2. Write the Haworth and the chair form of beta-D-mannopyranose. Compare
the structures with those for beta-D-glucopyranose.
3. Write all the steps in the mechanism by which open-chain D-ribose is
converted into a furanose hemiacetal form (beta-D-ribofuranose), followed
by conversion to an acetal form with methanol (methyl beta-D-ribofuranoside).