Quiz #5 (27 points)
CEM252
Name:_______________
PID:_________________
Section:______________
1. Determine whether the following pairs of structures are Enantioners, Diastereomers,
Epimers or Identical. (3 pts each)
H
HO
H
HO
CHO
OH
H
OH
H
CH2OH
HO
HO
HO
H
CHO
H
H
H
OH
CH2OH
vs
vs
H
HO
HO
HO
CHO
OH
H
H
H
CH2OH
HO
HO
HO
HO
CHO
H
H
H
CH2OH
H
Epimers
Identical
2. Circle the correct answer. (3 pts each)
a. Which of the following is the structure of D-Fructose?
H
HO
HO
HO
CHO
OH
H
H
H
CH2OH
CH2OH
O
H
HO
H
OH
H
OH
CH2OH
H
HO
H
H
CHO
OH
H
OH
OH
CH2OH
CH2OH
O
HO
H
HO
H
H
OH
CH2OH
b. Which of the following is a ketotetrose?
H
HO
CHO
OH
H
CH2OH
CH2OH
O
H
HO
CH2OH
CHO
H
HO
H
HO
H
OH
CH2OH
CHO
O
HO
H
H
OH
CH2OH
c. Which of the following is NOT a reducing sugar?
OH
CH2OH
O
OH
OH
CH2OH
O
CH2OH
O
HOH2C
OH
O
OH
OH
CH2OH
OH
HO
OH
OH
OH
HO
OH
OH
OMe
d. Which of the following is the Haworth projection (β-anomer) of the following sugar?
CH2OH
O
H
HO
H
HO
H
OH
CH2OH
HOH2C
Haworth
CH2OH
O
OH
OH
OH
!-anomer
HOH2C
HOH2C
OH
O
OH
CH2OH
OH
CH2OH
O
OH
HOH2C
OH
OH
O
OH
OH
CH2OH
OH
e. Which of the following is the chair form (α-anomer) of the following sugar?
HO
H
HO
H
CHO
H
OH
H
OH
CH2OH
OH
CH2OH
O
OH
OH
CH2OH
O
chair
OH
!-anomer
HO
OH
OH
HO
OH
CHO
OH
H
OH
CH2OH
1. NaCN, HCl
2. H2, Lindlar's
3. H3O+
OH
OH
Br2/H2O
H
H
HO
H
H
HO
H
CH2OH
O
OH
OH
3. What is the product of the following reactions?
H
HO
H
OH
CH2OH
O
CHO
OH
OH
H
OH
CH2OH
COOH
OH
H
OH
CH2OH
OH
OH