Campus CHM 231, Exam 4 – Carbohydrate Sample Problems

Dr. Spurgeon Answer Key

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
CHO CHO
CHO
H OH H OH
HO H
H OH H OH
H OH
HO H HO H
HO H
H OH H OH
H OH
CH2OH CH2OH
CH2OH

equitorial
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. OH OH

H O
H
H OH
H OH

OH H

Anomeric carbon
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
CH2OH H OH
H OH
a. O H
H H
H OH O
H
HO
H H
H OH H H
OH OH H OH
H OH OH OH
OH OH

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

1
 CH2OH
CHO
H OH
O OH
HO H H
OH O
H
HO
b. HO H OH OH
HO OH
OH H H H
H OH
H H
H H
H OH

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