CHEM 3111 Chapter 24 Practice Problems Nov 15, 2021

Name: ______________________

1. Plants convert carbon dioxide and water into glucose in presence of sunlight via
________.
A) hydrolysis
B) retrosynthesis
C) Killiani synthesis
D) photosynthesis
E) none of these

2. A monosaccharide with five carbon atoms and a ketone functional group is called a
_____.
A) aldose
B) ketohexose
C) aldopentose
D) ketopentose
E) pentose

3. Which of the following is an aldohexose?

O H
CH2OH C
O H O H
C O C H OH CH2OH

HO H HO H H OH HO H O

HO H H OH H OH H OH HO H

H OH H OH H OH H OH H OH

CH2OH CH2OH CH2OH CH2OH CH2OH

D-lyxose D-fructose D-ribose D-glucose D-xylulose

A) D-lyxose
B) D-fructose
C) D-ribose
D) D-glucose
E) D-xylulose
4. Which of the following best describes the relationship between D-glucose and D-
fructose?
A) enantiomers
B) epimers
C) anomers
D) constitutional isomers
E) diastereomers

5. Which of the following compounds are a pair of enantiomers?

A) I & III
B) II & IV
C) III & V
D) IV
E) none of these

6. Of the possible stereoisomers for fructose (including fructose), how many are D-
isomers?
A) 8
B) 6
C) 10
D) 2
E) 4
7. Which one of the following is the correct stereochemical configuration for D-mannose?

A) 2S,3S,4R,5R
B) 2R,3S,4R,5S
C) 2R,3R,4S,5S
D) 2S,3S,4R,5S
E) 2S,3R,4S,5R

8. Which of the following structures represent b-D-glucopyranose?

OHOH H OH H OH OHOH
OHO H O H O OHO
H HO HO H
H OH HO OH H H HO OH
H H H OH H OH H H
OH H H H OH OH H H
II III IV
I
A) I
B) II
C) III
D) IV
E) none of these
 9. Which of the following compounds is(are) an epimer(s) of D-glucose?
O H O H O H O H
C C C C

HO H HO H H OH H OH

HO H HO H HO H HO H

H OH H OH HO H HO H

H OH HO H H OH HO H

I
CH2OH
II CH2OH III CH2OH IV CH2OH
A) I
B) II
C) I & III
D) II &IV
E) I & II

10. Predict the major product for the following reaction.

A) I
B) II
C) III
D) IV
E) none of these
11. What is the correct Haworth projection for b-D-allopyranose?

A) I
B) II
C) III
D) IV
E) V

12. Which of the following compound(s) is a glycoside?

A) I
B) II
C) II & III
D) III & IV
E) II, III & IV
13. Predict the product(s) for the following reaction.

A) I
B) II
C) III
D) IV
E) II & IV

14. Which of the following D-aldoses will produce an optically inactive product when
treated with NaBH4/H2O?

A) I
B) II
C) III
D) IV
E) none of these
15. Which one of the following compounds is a non-reducing sugar?
OH OH OCH3 OH OH
CH2OH OH
O
O O O OH
HO
OH OH CH2OH
HO HO
OH OH OH OH
I II OH III OCH3 IV
A) I
B) II
C) III
D) IV
E) none of these

16. Predict the product(s) for the following reaction.

17. Predict the product(s) for the following reaction.

A) I
B) II
C) III
D) IV
E) V

18. Which aldose would produce D-ribose and D-arabinose when subjected to the
Kiliani-Fischer synthesis?
A) D-threose
B) D-xylose
C) D-erythrose
D) D-allose
E) D-Lyxose
19. Predict the product(s) for the following Kiliani-Fischer synthesis.

A) I&V
B) II & IV
C) I & III
D) III & IV
E) II & V

20. Predict the product(s) for the following Wohl degradation.

A) I
B) II
C) III
D) IV
E) V
 21. Which of the following disaccharides is a reducing sugar?

A) I
B) II
C) III
D) IV
E) none of these

22. Which of the following disaccharides is(are) a-glucoside(s)?

A) sucrose
B) maltose
C) lactose
D) cellobiose
E) both A & B

23. Which of the following monosaccharide(s) are produced when starch is completely
hydrolyzed?
A) a-D-glucose
B) b-D-glucose
C) a-D-galactose
D) b-D-fructose
E) maltose

24. Draw a Haworth projection and a chair of a-D-Gulose.

25. .Draw a chair confirmation of the disaccharide formed two molecules of D-Allose linked by a
1 à 4 b-D-glycosidic linkage.