Campus CHM 231, Exam 4 – Carbohydrate Sample Problems

Dr. Spurgeon
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1. Draw the following sugars as Fischer projections. Then answer the questions.
HO
CH2OH OH
H
a. b. OH
O H c.
H HO H O
H OH * H
H

H OH HO
H OH
OH H

d. b-D-Glucopyranose is the most abundant, naturally-occurring, sugar because all of its substituents are in ____________________
positions in the chair conformation.

e. Is the chair conformation represented in part c above the most stable chair conformation for this sugar? If not, redraw the chair so
that it does represent the most stable conformation for the sugar shown.

f. What is the name given to the carbon highlighted with the asterisk (*) in part b above? _______________________.

2. Provide both the requisite Haworth and most stable chair conformation for the sugars below.

CHO

H OH
a.
H OH

H OH

H OH

CH2OH
Haworth Projection of Most Stable Chair Conformation
D-Allose a-D-Allopyranose of a-D-Allopyranose

1
 CHO

HO H

b. HO H

H OH

H OH

CH2OH
Haworth Projection of Most Stable Chair Conformation
D-Mannose b-D-Mannopyranose of b-D-Mannopyranose