Chapter 15

General, Organic & Biological Chemistry, 5e (Timberlake)
Chapter 15 Carbohydrates
15.1 Multiple-Choice Questions
1) A carbohydrate that gives two molecules when it is completely hydrolyzed is known as a

A) monosaccharide.
B) disaccharide.
C) polysaccharide.
D) starch.
E) trisaccharide.
Answer: B
Objective: 15.1
Global Outcomes: GO2
2) Which group of carbohydrates cannot be hydrolyzed to give smaller molecules?

A) monosaccharides
B) disaccharides
C) trisaccharides
D) oligosaccharides
E) polysaccharides
Answer: A
Objective: 15.1
3) A monosaccharide that consists of 5 carbon atoms, one of which is in a ketone group, is classified as
a(n)
A) aldotetrose.
B) aldopentose.
C) aldohexose.
D) ketotetrose.
E) ketopentose.
Answer: E
Objective: 15.1
4) A monosaccharide that contains 4 carbon atoms, one of which is in an aldehyde group, is classified as
a(n)
A) aldopentose.
B) aldohexose.
C) ketopentose.
D) aldotetrose.
E) ketotetrose.
Answer: D
Objective: 15.1
1
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5) Which of the following is an example of an aldopentose?
A)
B)
C)
D)
E)
Answer: C
Objective: 15.1
2
6) Ribulose has the following structural formula. To what carbohydrate class does ribulose belong?
CH2OH
∣
C=O
∣
H - C - OH
∣
H - C - OH
∣
CH2OH
A) aldotetrose
B) aldopentose
C) ketotetrose
D) ketopentose
E) ketohexose
Answer: D
Objective: 15.1
7) During photosynthesis, carbon dioxide and water are converted to glucose and oxygen by
A) large animals.
B) insects.
C) mushrooms.
D) green plants.
E) earthworms.
Answer: D
Objective: 15.1
8) The breakdown of carbohydrates to carbon dioxide and water in the body is called
A) reduction.
B) respiration.
C) photosynthesis.
D) anabolism.
E) mutarotation.
Answer: B
Objective: 15.1
3
9) Which of the following is an example of a ketopentose?
A)
B)
C)
D)
E)
Answer: D
Objective: 15.1
4
10) Which of the following is an example of an aldohexose?
A)
B)
C)
D)
E)
Answer: E
Objective: 15.1
5
11) The breakdown of glucose to chemical energy for the cells to do work is an example of
A) oxidation.
B) respiration.
C) reduction.
D) anabolism.
E) mutarotation.
Answer: A
Objective: 15.1
12) Photosynthesis uses ________ as an energy source.

A) glucose
B) carbon dioxide
C) chlorophyll
D) oxygen
E) sunlight
Answer: E
Objective: 15.1
13) Fructose does not undergo hydrolysis because it is a

A) aldose.
B) hexose.
C) reducing sugar.
D) monosaccharide.
E) disaccharide.
Answer: D
Objective: 15.1
14) Galactosemia is the name of a metabolic disorder. In this disorder, an enzyme is missing that is
needed to
A) make galactose from lactose.
B) make lactose from galactose.
C) convert galactose to glycogen.
D) convert galactose to glucose.
E) convert α-galactose to β-galactose.
Answer: D
Objective: 15.2
6
15) Which Fischer projection is the mirror image of the structure given below?
Br
∣
HO — Cl
∣
CH3
A) Br
∣
HO — CH3
∣
Cl
B) Br
∣
Cl — OH
∣
CH3
C) OH
∣
CH3 — Cl
∣
Br
D) CH3
∣
Br — Cl
∣
OH
E) Br
∣
CH3 — Cl
∣
OH
Answer: B
Objective: 15.2
7
16) In the L- isomer of a Fischer projection of a monosaccharide, the -OH group furthest from the
carbonyl is written
A) on the left of the top chiral carbon.
B) on the right of the top chiral carbon.
C) on the left of the middle chiral carbon.
D) on the left of the bottom chiral carbon.
E) on the right of the bottom chiral carbon.
Answer: D
Objective: 15.2
17) One difference between D-glucose and L-glucose is

A) the open-chain form of L-glucose does not exist.
B) it is not possible to make L-glucose.
C) L-glucose has a 5-membered ring, and D-glucose has a 6-membered ring.
D) only D-glucose is found in disaccharides and polysaccharides.
E) L-glucose cannot form a closed structure.
Answer: D
Objective: 15.2
18) Hyperglycemia is a condition in which

A) the glucose level in the blood is about 100 mg/dL.
B) the amount of glucose in the urine is lower than normal.
C) the glucose level in the blood is higher than normal.
D) the glucose level in the pancreas is lower than normal.
E) the glucose level in the liver is lower than normal.
Answer: C
Objective: 15.2
19) Hypoglycemia is a condition in which

A) the glucose level in the blood is about 100 mg/dL.
B) the amount of glucose in the urine is higher than normal.
C) the glucose level in the blood is higher than normal.
D) the glucose level in the pancreas is higher than normal.
E) the glucose level in the blood is lower than normal.
Answer: E
Objective: 15.2
8
20) The sugar also known as dextrose and blood sugar is
A) glucose.
B) galactose.
C) fructose.
D) lactose.
E) sucrose.
Answer: A
Objective: 15.2
21) Galactose has the structure shown below. It can be classified as a(n)
A) ribose.
B) ketose.
C) disaccharide.
D) monosaccharide.
E) ketone.
Answer: D
Objective: 15.3
22) Galactose has the structure shown below. Which anomer is shown?
A) the α anomer
B) the β anomer
C) the D anomer
D) the L anomer
E) none of the above
Answer: B
Objective: 15.3
9
23) Mannose has the structure shown below. Which anomer is shown?
A) the α anomer
B) the β anomer
C) the D anomer
D) the L anomer
E) none of the above
Answer: A
Objective: 15.3
24) The conversion between α and β anomers is called

A) oxidation.
B) reduction.
C) glycoside.
D) mutarotation.
E) hydrolysis.
Answer: D
Objective: 15.3
25) The reduction of monosaccharides produces

A) sugar alcohols.
B) disaccharides.
C) trisaccharides.
D) sugar acids.
E) polysaccharides.
Answer: A
Objective: 15.4
26) The oxidation of monosaccharides produces

A) sugar alcohols.
B) disaccharides.
C) trisaccharides.
D) sugar acids.
E) polysaccharides.
Answer: D
Objective: 15.4
10
27) A glycosidic bond between two monosaccharides can also be classified as a(n)
A) double bond.
B) ester bond.
C) ether bond.
D) achiral bond.
E) alcohol bond.
Answer: C
Objective: 15.5
28) In a disaccharide, two monosaccharides are joined by what kind of bond?

A) double
B) anomeric
C) alcohol
D) glycosidic
E) rotational
Answer: D
Objective: 15.5
29) Which of the following contains a β-1,4-glycosidic bond?

A) galactose
B) lactose
C) maltose
D) sucrose
E) amylose
Answer: B
Objective: 15.5
30) Which sugar is NOT a reducing sugar?

A) glucose
B) fructose
C) galactose
D) maltose
E) sucrose
Answer: E
Objective: 15.5
31) Aspartame® and Saccharin® are two examples of

A) disaccharides.
B) polysaccharides.
C) chlorosaccharides.
D) alcohol sweeteners.
E) noncarbohydrate sweeteners.
Answer: E
Objective: 15.5
11
Refer to the disaccharides below to answer the question(s) that follow.
32) In the figure above, the monosaccharide unit at the top is a(n)
A) aldopentose.
B) ketopentose.
C) aldohexose.
D) aldoheptose.
E) ketohexose.
Answer: E
Objective: 15.5
33) In the figure above, the monosaccharide unit on the bottom is a(n)
A) aldopentose.
B) ketopentose.
C) aldohexose.
D) aldoheptose.
E) ketohexose.
Answer: C
Objective: 15.5
34) Hydrolysis of the disaccharide above gives the monosaccharides

A) fructose and ribose.
B) fructose and galactose.
C) ribose and glucose.
D) ribose and galactose.
E) fructose and lactose.
Answer: B
Objective: 15.5
12
35) The disaccharide above contains a(n) ________-glycosidic linkage.
A) α-1,4
B) β-1,4
C) α-2,4
D) β-2,4
E) α-2,6
Answer: E
Objective: 15.5
36) Maltose is a
A) monosaccharide.
B) disaccharide.
C) trisaccharide.
D) polysaccharide.
E) phosphosaccharide.
Answer: B
Objective: 15.5
37) Galactose is a product of enzymatic hydrolysis of

A) lactose.
B) glucose.
C) maltose.
D) erythrose.
E) sucrose.
Answer: A
Objective: 15.5
38) Maltose can be classified as a(n)

A) disaccharide.
B) polysaccharide.
C) ketose.
D) pentose.
E) oligosaccharide.
Answer: A
Objective: 15.5
39) Which of the following contains α-1,6-branches?

A) amylose
B) glycogen
C) cellulose
D) sucrose
E) maltose
Answer: B
Objective: 15.6
13
40) Cellulose is not digestible by humans because it contains glucose units linked by ________-glycosidic
bonds.
A) α-1,2
B) α-1,4
C) α-1,6
D) β-1,2
E) β-1,4
Answer: E
Objective: 15.6
41) Amylose is a polysaccharide which has

A) only β-1,4-bonds between glucose units.
B) only α-1,4-links bonds glucose units.
C) both α-1,4-and β-1,4-bonds between glucose units.
D) hemiacetal links joining glucose units.
E) carbon-carbon bonds joining glucose units.
Answer: B
Objective: 15.6
42) Humans cannot digest cellulose because they

A) lack the necessary enzymes to digest β-glycosides.
B) are allergic to β-glycosides.
C) are poisoned by β-glycosides.
D) have intestinal flora which use up β-glycosides.
E) cannot digest chlorophyll.
Answer: A
Objective: 15.6
43) Under acid hydrolysis conditions, starch is converted to

A) glucose.
B) xylose.
C) maltose.
D) galactose.
E) fructose.
Answer: A
Objective: 15.6
14
44) Amylopectin is a polysaccharide which has
D) both α-1,4-and α-1,6-bonds between glucose units.
Answer: D
Objective: 15.6
45) Glycogen is a polysaccharide which has

D) both α-1,4-and α-1,6-bonds between glucose units.
Answer: D
Objective: 15.6
15.2 Short Answer Questions
State whether each of these structures is the α- or β-form.
1)
Answer: α (alpha)
Objective: 15.3
2)
Answer: β (beta)
Objective: 15.3
15
3)
Answer: α (alpha)
Objective: 15.3
4)
Answer: α (alpha)
Objective: 15.3
5)
Answer: β (beta)
Objective: 15.3
16
Identify each Fischer projection as the D- or L-isomer.
6)
Answer: D
Objective: 15.2
7)
Answer: L
Objective: 15.2
8)
Answer: L
Objective: 15.2
17
9)
Answer: L
Objective: 15.2
10)
Answer: D
Objective: 15.2
15.3 True/False Questions
1) A monosaccharide can be hydrolyzed to smaller units.

Answer: FALSE
Objective: 15.1
2) Fructose is also known as dextrose.

Answer: FALSE
Objective: 15.2
3) Fructose is a ketohexose.
Answer: TRUE
Objective: 15.2
4) In the D- isomer, the -OH farthest from the carbonyl is to the left.
Answer: FALSE
Objective: 15.2
18
5) In the α anomer of glucose, the OH on carbon 1 is above the plane of the ring.
Answer: FALSE
Objective: 15.3
6) This anomer is the α anomer
Answer: FALSE
Objective: 15.3
7) A reducing sugar gives a precipitate of silver metal with Benedict's reagent.

Answer: FALSE
Objective: 15.4
8) Cellulose will give a positive Benedict's test.

Answer: FALSE
Objective: 15.4
9) The product of oxidation of an aldose is a carboxylic acid.

Answer: TRUE
Objective: 15.4
10) The product of reduction of mannose is mannic acid.

Answer: FALSE
Objective: 15.4
11) Sucrose is a reducing sugar.

Answer: FALSE
Objective: 15.4
12) Maltose is a reducing sugar.

Answer: TRUE
Objective: 15.4
13) The product of reduction of xylose is xylitol.

Answer: TRUE
Objective: 15.4
19
14) Sucrose is made up of glucose units only.
Answer: FALSE
Objective: 15.5
15) Galactose is a disaccharide.

Answer: FALSE
Objective: 15.5
16) Sucrose is a disaccharide.

Answer: TRUE
Objective: 15.5
17) The iodine test is used to detect the presence of a reducing sugar.
Answer: FALSE
Objective: 15.6
18) Glucose is stored in animals as glycogen.

Answer: TRUE
Objective: 15.6
19) Amylopectin is a straight-chain polysaccharide.

Answer: FALSE
Objective: 15.6
20) Cellulose is a polysaccharide with only β-1,4-bonds between glucose units.

Answer: TRUE
Objective: 15.6
20
15.4 Matching Questions
Select the correct carbohydrate for each description.
A) amylose
B) fructose
C) lactose
D) cellulose
E) galactose
F) glycogen
G) maltose
H) sucrose
1) a carbohydrate that cannot be digested by humans

Objective: 15.2, 15.5, 15.6
2) a disaccharide that occurs as a breakdown product of starch

Objective: 15.2, 15.5, 15.6
3) a carbohydrate that stores energy in the human body

Objective: 15.2, 15.5, 15.6
4) a carbohydrate that is used to build cell walls in plants

Objective: 15.2, 15.5, 15.6
5) a monosaccharide that combines with glucose to form lactose

Objective: 15.2, 15.5, 15.6
6) a disaccharide found in milk and milk products

Objective: 15.2, 15.5, 15.6
7) a disaccharide consisting of glucose and fructose

Objective: 15.2, 15.5, 15.6
8) a disaccharide consisting of two glucose molecules

Objective: 15.2, 15.5, 15.6
9) a monosaccharide found in fruit juices and honey, the sweetest carbohydrate

Objective: 15.2, 15.5, 15.6
21
10) an unbranched carbohydrate that stores glucose in plants
Objective: 15.2, 15.5, 15.6
Answers: 1) D 2) G 3) F 4) D 5) E 6) C 7) H 8) G 9) B 10) A
Indicate the monosaccharide(s) produced upon hydrolysis of each carbohydrate.
A) glucose + fructose
B) glucose
C) glucose + galactose
11) amylopectin
Objective: 15.5, 15.6
12) lactose
13) glycogen
14) maltose
15) sucrose
Answers: 11) B 12) C 13) B 14) B 15) A
22

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Chapter 15

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General, Organic & Biological Chemistry, 5e (Timberlake)

15.1 Multiple-Choice Questions

1) A carbohydrate that gives two molecules when it is completely hydrolyzed is known as a

2) Which group of carbohydrates cannot be hydrolyzed to give smaller molecules?

12) Photosynthesis uses ________ as an energy source.

13) Fructose does not undergo hydrolysis because it is a

17) One difference between D-glucose and L-glucose is

18) Hyperglycemia is a condition in which

19) Hypoglycemia is a condition in which

24) The conversion between α and β anomers is called

25) The reduction of monosaccharides produces

26) The oxidation of monosaccharides produces

28) In a disaccharide, two monosaccharides are joined by what kind of bond?

29) Which of the following contains a β-1,4-glycosidic bond?

30) Which sugar is NOT a reducing sugar?

31) Aspartame® and Saccharin® are two examples of

34) Hydrolysis of the disaccharide above gives the monosaccharides

37) Galactose is a product of enzymatic hydrolysis of

38) Maltose can be classified as a(n)

39) Which of the following contains α-1,6-branches?

41) Amylose is a polysaccharide which has

42) Humans cannot digest cellulose because they

43) Under acid hydrolysis conditions, starch is converted to

45) Glycogen is a polysaccharide which has

15.2 Short Answer Questions

State whether each of these structures is the α- or β-form.

15.3 True/False Questions

1) A monosaccharide can be hydrolyzed to smaller units.

2) Fructose is also known as dextrose.

6) This anomer is the α anomer

7) A reducing sugar gives a precipitate of silver metal with Benedict's reagent.

8) Cellulose will give a positive Benedict's test.

9) The product of oxidation of an aldose is a carboxylic acid.

10) The product of reduction of mannose is mannic acid.

11) Sucrose is a reducing sugar.

12) Maltose is a reducing sugar.

13) The product of reduction of xylose is xylitol.

15) Galactose is a disaccharide.

16) Sucrose is a disaccharide.

18) Glucose is stored in animals as glycogen.

19) Amylopectin is a straight-chain polysaccharide.

20) Cellulose is a polysaccharide with only β-1,4-bonds between glucose units.

Select the correct carbohydrate for each description.

1) a carbohydrate that cannot be digested by humans

2) a disaccharide that occurs as a breakdown product of starch

3) a carbohydrate that stores energy in the human body

4) a carbohydrate that is used to build cell walls in plants

5) a monosaccharide that combines with glucose to form lactose

6) a disaccharide found in milk and milk products

7) a disaccharide consisting of glucose and fructose

8) a disaccharide consisting of two glucose molecules

9) a monosaccharide found in fruit juices and honey, the sweetest carbohydrate

Indicate the monosaccharide(s) produced upon hydrolysis of each carbohydrate.

Answers: 11) B 12) C 13) B 14) B 15) A

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