Chemistry Chapter 24 1 Which one of the following is the correct stereochemical

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subject Textbook Organic Chemistry 1st Edition
subject Authors David R. Klein
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Chapter Twenty Four
1.
Which of the following is a ketohexose?
CH2OH
O
HHO
OHH
OHH
CH2OH
C
OHH
OHH
OHH
CH2OH
O H
C
OHH
HHO
OHH
OHH
CH2OH
O H
D-lyxose D-fructose D-ribose D-glucose
CH2OH
O
HHO
OHH
CH2OH
D-xylulose
C
HHO
HHO
OHH
CH2OH
O H
A)
D-lyxose
B)
D-fructose
C)
D-ribose
D)
D-glucose
E)
D-xylulose
2.
Which of the following is an aldohexose?
A)
D-xylose
B)
D-galactose
C)
D-fructose
D)
D-ribose
E)
D-erythrose
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3.
Which of the following is a ketopentose?
CH2OH
O
HHO
OHH
OHH
CH2OH
C
OHH
OHH
OHH
CH2OH
O H
C
OHH
HHO
OHH
OHH
CH2OH
O H
D-lyxose D-fructose D-ribose D-glucose
CH2OH
O
HHO
OHH
CH2OH
D-xylulose
C
HHO
HHO
OHH
CH2OH
O H
A)
D-lyxose
B)
D-fructose
C)
D-ribose
D)
D-glucose
E)
D-xylulose
4.
Which of the following is an aldopentose?
A)
D-xylose
B)
D-galactose
C)
D-fructose
D)
D-ribulose
E)
D-erythrose
5.
Which of the following best describes L-xylulose?
A)
aldopentose
B)
aldohexose
C)
ketopentose
D)
ketohexose
E)
aldotetrose
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6.
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
7.
Which of the following is (are) L-aldohexose(s)?
C
OHH
HHO
OHH
OHH
CH2OH
O H
CH2OH
O
HHO
OHH
OHH
CH2OH
C
OHH
HHO
HHO
OHH
CH2OH
O H
C
OHH
HHO
OHH
HHO
CH2OH
O H
III III IV
CH2OH
O
HHO
OHH
HHO
CH2OH
V
A)
I
B)
II
C)
III
D)
IV
E)
V
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8.
Which of the following is (are) D-aldopentose(s)?
A)
I
B)
II
C)
III
D)
IV
E)
I & V
9.
Which of the following is (are) L-ketopentose(s)?
A)
I
B)
II
C)
III
D)
IV
E)
III & IV
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10.
Which of the following aldohexose(s) is (are) dextrorotatory?
A)
D-glucose
B)
D-galactose
C)
D-gulose
D)
D-mannose
E)
can not predict
11.
Which of the following compounds is a pair of enantiomers?
C
OHH
HHO
OHH
OHH
CH2OH
O H
C
H
HHO
OHH
OHH
CH2OH
HO
O H
C
OHH
HHO
HHO
OHH
CH2OH
O H
C
OHH
OHH
HHO
HHO
CH2OH
O H
III III IV V
C
OH
HHO
OHH
HHO
CH2OH
H
O H
A)
I & III
B)
II & IV
C)
III & V
D)
IV
E)
none of these
12.
How many stereoisomers are possible for L-galactose?
A)
8
B)
6
C)
10
D)
3
E)
4
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13.
Draw a Fisher projection for D-allose.
14.
Draw a Fisher projection for L-ribose.
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15.
Which one of the following is the correct Fischer projection for D-gulose?
C
OHH
HHO
OHH
OHH
CH2OH
O H
CH2OH
O
HHO
OHH
OHH
CH2OH
C
HHO
HHO
OHH
OHH
CH2OH
O H
C
OHH
OHH
HHO
HHO
CH2OH
O H
III III IV V
C
OHH
OHH
HHO
OHH
CH2OH
O H
A)
I
B)
II
C)
III
D)
IV
E)
V
16.
How many stereoisomers are possible for D-fructose?
A)
8
B)
6
C)
10
D)
3
E)
4
17.
How many stereoisomers are possible for D-xylulose?
A)
8
B)
6
C)
10
D)
2
E)
4
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18.
Draw a Fisher projection for D-sorbose.
19.
Draw a Fisher projection for D-erythrulose.
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20.
Which one of the following is the correct structure for L-fructose?
A)
I
B)
II
C)
III
D)
IV
E)
V
21.
Which one of the following is the correct stereochemical configuration for D-xylose?
C
OHH
HHO
OHH
CH2OH
O H
2
4
3
A)
2S,3R,4S
B)
2R,3S,4R
C)
2R,3R,4S
D)
2S,3S,4R
E)
2S,3S,4S
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22.
Which one of the following is the correct stereochemical configuration for D-mannose?
C
HHO
HHO
OHH
OHH
CH2OH
O H
2
3
4
5
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
23.
Which of the following best describes the relationship between D-glucose and D-
galactose?
A)
enantiomers
B)
anomers
C)
epimers
D)
constitutional isomers
E)
none of these
24.
Which of the following pairs of compounds are epimers?
A)
D-glucose & D-altose
B)
D-altose & D-mannose
C)
D-glucose & D-talose
D)
D-fructose & D-sorbose
E)
none of these
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25.
Which of the following compound(s) is(are) an epimer(s) of D-glucose?
C
HHO
HHO
OHH
OHH
CH2OH
O H
C
HHO
HHO
OHH
HHO
CH2OH
O H
C
OHH
HHO
HHO
OHH
CH2OH
O H
C
OHH
HHO
HHO
HHO
CH2OH
O H
III III IV
A)
I
B)
II
C)
I & III
D)
II &IV
E)
I & II
26.
Predict the major product for the following reaction.
HO H
O
H3O+
HO OH
OH
O OH O O O
OH
III III IV
A)
I
B)
II
C)
III
D)
IV
E)
none of these
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27.
Predict the major product for the following reaction.
HO
H
O
H3O+
O OH O O O
OH
III III IV
O
O
A)
I
B)
II
C)
III
D)
IV
E)
none of these
28.
Provide the reactant(s) for the following reaction.
H3O+
O
OH
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29.
Which carbon in the following monosaccharide is the anomeric carbon?
O
OH OH
OH
OH
CH2OH
I
II
III
IV
V
A)
I
B)
II
C)
III
D)
IV
E)
V
30.
What is the correct Haworth projection for -D-glucopyranose?
O
OH OH
OHOH
CH2OH
O
OH OH
OH
OH
CH2OH
O
OH
OH
OH
OH
CH2OH
O
OH
OH
OH
OH
CH2OH
O
OH OH
OH
OH
CH2OH
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
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31.
What is the correct Haworth projection for -D-allopyranose?
O
OH OH
OHOH
CH2OH
O
OH OH
OH
OH
CH2OH
O
OH
OH
OH
CH2OH
OH
O
OH
OH
OH
OH
CH2OH
O
OH OH
OH
OH
CH2OH
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
32.
What is the correct name for the following compound?
O
OH
OH
OH
OH
CH2OH
A)
-D-glucopyranose
B)
-D-allopyranose
C)
-D-glucopyranose
D)
-D-galactopyranose
E)
-D-gulopyranose
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33.
What is the correct name for the following compound?
O
CH2OH
OH
OH
OH
OH
A)
-D-idopyranose
B)
-D-altopyranose
C)
-D-glucopyranose
D)
-D-galactopyranose
E)
-D-gulopyranose
34.
Pyranose forms of monosaccharides are_____.
A)
−membered cyclic hemiacetals
B)
−membered cyclic acetals
C)
−membered cyclic acetals
D)
−membered cyclic hemiacetals
E)
none of these
35.
Furanose forms of monosaccharides are_____.
A)
−membered cyclic hemiacetals
B)
−membered cyclic acetals
C)
−membered cyclic acetals
D)
−membered cyclic hemiacetals
E)
none of these
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36.
Which of the following compound(s) would undergo mutarotation in aqueous solution?
O
OH
OH
OH
OH
CH2OH
O
OH OH
OH
OH
CH2OH
O
OH
OH
OH
OH
CH2OCH3
O
OH
OCH3
OH
OH
CH2OH
III III IV
A)
B)
  
C)
  V
D)
   
E)
all of these
37.
Which of the following compound(s) would NOT undergo mutarotation in aqueous
solution?
O
OH
OH
OH
OH
CH2OH
O
OH
OH
OH
OH
CH2OCH3
O
OH
OCH3
OH
OH
CH2OH
III
III IV
OCH3
CH2OH
OH OH
O
A)
B)
  V
C)

D)
V
E)
II, III & IV
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38.
What is the correct name for the following compound?
CH2OH
OH
CH2OH
OH
OH
O
A)
-D-fructofuranose
B)
-D-sorbofuranose
C)
-D-glucopyranose
D)
-D- fructofuranose
E)
-D-gulopyranose
39.
Draw the Haworth projection for -D-erythrofuranose.
40.
Draw the chair conformation of -D-galactopyranose.
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41.
Draw the Fischer projection for open chain form of the following cyclic
monosaccharide.
O
OH
HO
OH
HO
OH
42.
Provide the reagents necessary to carry out the following conversion.
O
OH
HO
OH
HO
OH
O
O
O
O
O
O
O
O
O
O
O
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43.
Predict the product(s) when -D-galactopyranose reacts with excess acetic anhydride in
the presence of pyridine.
44.
Provide the reagents necessary to carry out the following conversion.
O
OH
HO
OH
HO
OH
O
O
O
O
O
O
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45.
Which of the following compound(s) is a glycoside?
O
OH
HO
OH
HO
OH
O
OCH3
HO
OH
HO
OH
III
O
OH
HO
OH
HO
OCH3
O
OH
OH
OCH3
OH
OH
IV
III
A)
B)

C)
  
D)
II & IV
E)
II, III & IV
46.
Provide the reagents necessary to carry out the following conversion.
O
OH
HO
OH
HO
OH
O
OH
HO
OH
HO
OCH3
O
OH
HO
OH
HO
OCH3
+

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