Test Bank for General, Organic, and Biological Chemistry, 4th Edition, Laura D.

Frost

Test Bank for General, Organic, and Biological

Chemistry, 4th Edition, Laura D. Frost

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Chapter 6 Carbohydrates - Life's Sweet Molecules

6.1 Multiple-Choice

1) Which of the following is a polysaccharide?

A) Glucose
B) Sucrose
C) Starch
D) Maltose
Answer: C
Diff: 1
Section: 6-1
Global: G1
LO: 6.1

2) Which of the following is a disaccharide?

A) Glucose
B) Sucrose
C) Starch
D) Mannose
Answer: B
Diff: 1
Section: 6-1
Global: G1
LO: 6.1

3) Which of the following is a monosaccharide

A) Mannose
B) Sucrose
C) Starch
D) Maltose
Answer: A
Diff: 1
Section: 6-1, 6-5
Global: G1
LO: 6.1

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4) Identify all the disaccharides from the following list:
i) Lactose
ii) Glucose
iii) Ribose
iv) Maltose
A) i + iv
B) ii + iii
C) i + ii
D) iii + iv
Answer: A
Diff: 1
Section: 6-1, 6-5
Global: G1
LO: 6.1

5) How many monosaccharides are connected to each other in a disaccharide?

A) 1
B) 2
C) 3
D) 4
Answer: B
Diff: 1
Section: 6-1
Global: G1
LO: 6.1

6) How many monosaccharides are connected to each other in an oligosaccharide?

A) 1
B) 2
C) 3-9
D) more than 9
Answer: C
Diff: 1
Section: 6-1
Global: G1
LO: 6.1

7) The general formula for a carbohydrate is:

A) CnH2n+2
B) Cn(H2O)n
C) CnH2n
D) Cn(H2O)
Answer: B
Diff: 1
Section: 6-1
Global: G1
LO: 6.1
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8) Which of the following functional groups is just a carbon double bonded to an oxygen atom?
A) Alcohol
B) Thiol
C) Carbonyl
D) Ester
Answer: C
Diff: 1
Section: 6-1, 6-2
Global: G1
LO: 6.2

9) Which of the following functional groups comprises a carbon atom bonded to a hydroxyl
group?
A) Alcohol
B) Thiol
C) Carbonyl
D) Ester
Answer: A
Diff: 1
Section: 6-1, 6-2
Global: G1
LO: 6.2

10) A carbohydrate with an aldehyde functional group is called:

A) ketose
B) aldose
C) disaccharide
D) hexose
Answer: B
Diff: 1
Section: 6-2
Global: G1
LO: 6.2

11) A carbohydrate with a ketone functional group is called:

A) ketose
B) aldose
C) disaccharide
D) hexose
Answer: A
Diff: 1
Section: 6-2
Global: G1
LO: 6.2

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12) A carbohydrate with 5 carbons is called a:
A) hexose
B) triose
C) pentose
D) tetrose
Answer: C
Diff: 1
Section: 6-2
Global: G1
LO: 6.2

13) A carbohydrate with 4 carbons is called a:

A) hexose
B) triose
C) pentose
D) tetrose
Answer: D
Diff: 1
Section: 6-2
Global: G1
LO: 6.2

14) A carbohydrate with 6 carbons and an aldehyde functional group is called a(n):
A) ketohexose
B) aldohexose
C) ketopentose
D) aldopentose
Answer: B
Diff: 1
Section: 6-2
Global: G1
LO: 6.2

15) A carbohydrate with 6 carbons and a ketone functional group is called a(n):
A) ketohexose
B) aldohexose
C) ketopentose
D) aldopentose
Answer: A
Diff: 1
Section: 6-2
Global: G1
LO: 6.2

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16) The most abundant monosaccharide in nature is:
A) mannose
B) galactose
C) glucose
D) fructose
Answer: C
Diff: 1
Section: 6-2
Global: G1
LO: 6.2

17) Galactose is called a(n):

A) aldopentose
B) ketohexose
C) aldohexose
D) ketopentose
Answer: C
Diff: 1
Section: 6-2
Global: G1
LO: 6.2

18) Fructose is called a(n):

A) aldopentose
B) ketohexose
C) aldohexose
D) ketopentose
Answer: B
Diff: 1
Section: 6-2
Global: G1
LO: 6.2

19) Ribose is a(n):

A) aldohexose
B) ketohexose
C) aldopentose
D) ketopentose
Answer: C
Diff: 1
Section: 6-3
Global: G1
LO: 6.3

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20) Glyceraldehyde is a carbohydrate that contains ________ carbon atoms.
A) 3
B) 4
C) 5
D) 6
Answer: A
Diff: 1
Section: 6-2
Global: G1
LO: 6.2

21) Which of the following is a tertiary alcohol?

A)

B)

C)

D)

Answer: B
Diff: 1
Section: 6-2
Global: G2
LO: 6.2

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22) Which of the following is a primary alcohol?
A)

B)

C)

D)

Answer: C
Diff: 1
Section: 6-2
Global: G2
LO: 6.2

23) Which of the following is a secondary alcohol?

A)

B)

C)

D)

Answer: A
Diff: 1
Section: 6-2
Global: G2
LO: 6.2
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24) Which of the following is a tertiary alcohol?
A)

B)

C)

D)

Answer: B
Diff: 2
Section: 6-2
Global: G2
LO: 6.2

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25) Which of the following is an aldehyde functional group?
A)

B)

C)

D)

Answer: B
Diff: 1
Section: 6-2
Global: G1
LO: 6.2

26) Which of the following is a ketone functional group?

A)

B)

C)

D)

Answer: C
Diff: 1
Section: 6-2
Global: G1
LO: 6.2

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27) Which of the following is a ketone?
A)

B)

C)

D)

Answer: D
Diff: 1
Section: 6-2
Global: G2
LO: 6.2

28) What types of alcohols are found in carbohydrates?

A) Primary only
B) Secondary only
C) Tertiary only
D) Primary + secondary
Answer: D
Diff: 1
Section: 6-2
Global: G1
LO: 6.2
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29) Which of these carbohydrates shown in the Fischer projection is D-galactose?
A)

B)

C)

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D)

Answer: A
Diff: 2
Section: 6-2, 6-3
Global: G2
LO: 6.3

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30) Which of these molecules is an aldopentose?
A)

B)

C)

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D)

Answer: D
Diff: 2
Section: 6-2, 6-3
Global: G2
LO: 6.3

31) How many stereoisomers are possible for:

A) 1
B) 2
C) 4
D) 8
Answer: D
Diff: 3
Section: 6-3
Global: G2
LO: 6.3

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32) How many chiral carbon atoms are there in this molecule?

A) 1
B) 2
C) 3
D) 4
Answer: B
Diff: 2
Section: 6-3
Global: G2
LO: 6.3

33) How many chiral carbon atoms are in this molecule:

A) 3
B) 4
C) 5
D) 6
Answer: B
Diff: 2
Section: 6-3
Global: G2
LO: 6.3

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34) The configuration at which carbon atom determines if a monosaccharide is D or L?
A) The lowest numbered chiral carbon
B) The highest numbered chiral carbon
C) The chiral carbon closest to the aldehyde or keto group
D) The carbon of the primary alcohol group
Answer: B
Diff: 1
Section: 6-3
Global: G1
LO: 6.3

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35) Which of the following compounds is the enantiomer of the following?

A)

B)

C)

D)

Answer: B
Diff: 2
Section: 6-3
Global: G2
LO: 6.3

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36) Glucose and galactose are ________ of each other.
A) anomers
B) enantiomers
C) epimers
D) cis-trans isomers
Answer: C
Diff: 1
Section: 6-3
Global: G1
LO: 6.3

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37) Which of these molecules is the enantiomer of D-altrose?

A)

B)

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C)

D)

Answer: A
Diff: 2
Section: 6-3
Global: G2
LO: 6.3

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38) Which one of these molecules is an epimer of D-allose?

A)

B)

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C)

D)

Answer: C
Diff: 2
Section: 6-3
Global: G2
LO: 6.3

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39) Which of the following is a pyranose ring?
A)

B)

C) Both of these are pyranose rings.

D) Neither of these is a pyranose ring.
Answer: B
Diff: 2
Section: 6-4
Global: G1
LO: 6.4

40) Which of the following is a furanose ring?

A)

B)

C) Both of these are furanose rings.

D) Neither of these is a furanose ring.
Answer: A
Diff: 2
Section: 6-4
Global: G1
LO: 6.4

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41) α-D-glucose and β-D-glucose are:
A) enantiomers
B) anomers
C) disaccharides
D) a racemic mixture
Answer: B
Diff: 1
Section: 6-4
Global: G1
LO: 6.4

42) When an organic molecule loses hydrogens it is said to be:

A) reduced
B) oxidized
C) both oxidized and reduced
D) neither oxidized or reduced
Answer: B
Diff: 1
Section: 6-4
Global: G1
LO: 5.4, 6.4

43) When an organic molecule gains hydrogens it is said to be:

A) reduced
B) oxidized
C) both oxidized and reduced
D) neither oxidized or reduced
Answer: A
Diff: 1
Section: 6-4
Global: G1
LO: 5.4, 6.4

44) When a substance is oxidized it is called a(n):

A) oxidizing agent
B) reducing agent
C) both
D) neither
Answer: B
Diff: 1
Section: 6-4
Global: G1
LO: 5.4, 6.4

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45) When a substance is reduced it is called a(n):
A) oxidizing agent
B) reducing agent
C) both
D) neither
Answer: A
Diff: 1
Section: 6-4
Global: G1
LO: 5.4, 6.4

46) In the Benedict's test:

A) an aldehyde is oxidized
B) a silver mirror is produced
C) the copper (II) ion is oxidized
D) all of these
Answer: A
Diff: 1
Section: 6-4
Global: G1
LO: 6.4

47) In the Benedict's test:

A) an aldehyde is oxidized
B) a brick red precipitate is formed
C) the copper (II) ion is reduced
D) all of the above are true
Answer: D
Diff: 1
Section: 6-4
Global: G1
LO: 6.4

48) The substance that precipitates in a positive Benedict test is:

A) Ag
B) CuO
C) Cu2O
D) none of these
Answer: C
Diff: 1
Section: 6-4
Global: G1
LO: 6.4

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49) Lactose is made from D-glucose and:
A) mannose
B) glucose
C) galactose
D) ribose
Answer: C
Diff: 1
Section: 6-5
Global: G1
LO: 6.5

50) Which of the following is a non-reducing sugar?

A) Lactose
B) Glucose
C) Mannose
D) Sucrose
Answer: D
Diff: 2
Section: 6-5
Global: G1
LO: 6.5

51) This disaccharide is also known as malt sugar since it is formed from the breakdown of
starch and is a key ingredient in beer:
A) sucrose
B) lactose
C) maltose
D) cellobiose
Answer: C
Diff: 1
Section: 6-5
Global: G1
LO: 6.5

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52) What type of glycosidic bond is shown here?

A) α(1→4)
B) α(1→6)
C) β(1→4)
D) β(1→6)
Answer: B
Diff: 2
Section: 6-5
Global: G2
LO: 6.5

27
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53) What type of glycosidic bond is shown here?

A) α(1→4)
B) α(1→6)
C) β(1→4)
D) β(1→6)
Answer: C
Diff: 2
Section: 6-5
Global: G2
LO: 6.5

54) The glycosidic bond that connects the two monosaccharides in lactose is:
A) α(1→4)
B) β(1→4)
C) α(1→6)
D) α,β(1→2)
Answer: B
Diff: 2
Section: 6-5
Global: G2
LO: 6.5

55) The glycosidic bond that connects the two monosaccharides in sucrose is:
A) α(1→4)
B) β(1→4)
C) α(1→6)
D) α,β(1→2)
Answer: D
Diff: 2
Section: 6-5
Global: G2
LO: 6.5

28
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56) Which of these polysaccharides is not made exclusively from α-glucose units?
A) Amylose
B) Amylopectin
C) Glycogen
D) Cellulose
Answer: D
Diff: 1
Section: 6-6
Global: G1
LO: 6.6

57) Which of the following is the storage form of glucose in the liver and muscle tissue?
A) Amylose
B) Amylopectin
C) Glycogen
D) Cellulose
Answer: C
Diff: 1
Section: 6-6
Global: G1
LO: 6.6

58) Which one of these polysaccharides is not used in energy storage?

A) Cellulose
B) Glycogen
C) Amylose
D) Amylopectin
Answer: A
Diff: 1
Section: 6-6
Global: G1
LO: 6.6

59) Which one of these polysaccharides contains β-N-acetylglucosamine units forming β(1→4)
bonds?
A) Cellulose
B) Chitin
C) Amylose
D) Amylopectin
Answer: B
Diff: 1
Section: 6-6
Global: G1
LO: 6.6

29
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60) Which of the following is the structural polysaccharide in plants?
A) Amylose
B) Amylopectin
C) Glycogen
D) Cellulose
Answer: D
Diff: 1
Section: 6-6
Global: G1
LO: 6.6

61) The polysaccharide the makes up the exoskeleton of insects is:

A) cellulose
B) glycogen
C) chitin
D) amylose
Answer: C
Diff: 1
Section: 6-6
Global: G1
LO: 6.6

62) Which blood type contains the carbohydrate N-acetylgalactosamine?

A) A
B) B
C) O
D) All blood types contain this carbohydrate.
Answer: A
Diff: 1
Section: 6-7
Global: G1
LO: 6.7

63) Which of the following blood types is considered to be the universal blood donor?
A) Type B
B) Type A
C) Type AB
D) Type O
Answer: D
Diff: 1
Section: 6-7
Global: G1
LO: 6.7

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6.2 True/False

1) This molecule represents a secondary alcohol:

Answer: FALSE
Diff: 1
Section: 6-2
Global: G2
LO: 6.2

2) This molecule represents a primary alcohol:

Answer: FALSE
Diff: 1
Section: 6-2
Global: G2
LO: 6.2

3) This molecule represents a tertiary alcohol:

Answer: TRUE
Diff: 1
Section: 6-2
Global: G2
LO: 6.2

31
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4) This molecule represents an aldehyde:

Answer: TRUE
Diff: 1
Section: 6-2
Global: G2
LO: 6.2

5) This molecule represents a ketone:

Answer: TRUE
Diff: 1
Section: 6-2
Global: G2
LO: 6.2

6) This molecule represents a ketopentose:

Answer: TRUE
Diff: 2
Section: 6-2, 6-3
Global: G2
LO: 6.2, 6.3

32
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7) This molecule represents an aldohexose:

Answer: TRUE
Diff: 2
Section: 6-2, 6-3
Global: G2
LO: 6.2, 6.3

8) This molecule represents the L enantiomer of galactose:

Answer: TRUE
Diff: 2
Section: 6-3
Global: G2
LO: 6.3

9) A carboxylic acid is formed by oxidation of an aldehyde.

Answer: TRUE
Diff: 1
Section: 6-4
Global: G1
LO: 5.4, 6.4

33
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10) An alcohol is formed by oxidation of a ketone.
Answer: FALSE
Diff: 1
Section: 6-4
Global: G1
LO: 5.4, 6.4

11) Polysaccharides are non-reducing sugars.

Answer: TRUE
Diff: 1
Section: 6-6
Global: G1
LO: 6.6

12) Starch is made from glucose units in α(1→4) glycosidic bonds.

Answer: TRUE
Diff: 1
Section: 6-6
Global: G1
LO: 6.6

13) Glycogen is the storage polysaccharide in animals.

Answer: TRUE
Diff: 1
Section: 6-6
Global: G1
LO: 6.6

6.3 Short Answer

1) Identify which structure contains a primary, secondary or tertiary alcohol in the following
structures.

A) ________ B) ________ C) ________

Answer: A) secondary; B) primary; C) tertiary
Diff: 1
Section: 6-2
Global: G2
LO: 6.2

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2) A secondary alcohol contains _______ alkyl groups attached to the C atom bonded to the
hydroxyl group.
Answer: two
Diff: 1
Section: 6-2
Global: G1
LO: 6.2

3) An aldopentose contains ________ carbon atoms and a/an ________ group.

Answer: five, aldehyde
Diff: 1
Section: 6-2
Global: G1
LO: 6.2

4) In the Fischer projection of a carbohydrate, the wedges are represented by ________ lines and
the dashes are represented by ________ lines.
Answer: horizontal, vertical
Diff: 1
Section: 6-3
Global: G1
LO: 6.3

5) All D-sugars have the -OH on the chiral center farthest from the carbonyl group on the
________ side of the molecule.
Answer: right
Diff: 1
Section: 6-3
Global: G1
LO: 6.3

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6) Draw the enantiomer of D-galactose.
Answer:

Diff: 2
Section: 6-3
Global: G2
LO: 6.3

7) Draw the enantiomer of L-altrose.

Answer:

Diff: 2
Section: 6-3
Global: G2
LO: 6.3

8) The number of stereoisomers of a molecule that contains n chiral carbon atoms is given by
________.
Answer: 2n
Diff: 2
Section: 6-3
Global: G2
LO: 6.3

36
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9) Stereoisomers that are not enantiomers are called ________.
Answer: diastereoisomers
Diff: 1
Section: 6-3
Global: G1
LO: 6.3

10) Diastereoisomers that differ in just one chiral center are called ________.
Answer: epimers
Diff: 1
Section: 6-3
Global: G1
LO: 6.3

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11) Given the following structure:

A) How many chiral carbons are contained in this compound? Identify each chiral carbon.
B) How many stereoisomers are possible for this compound?
C) Draw the Fisher projections for all of the possible stereoisomers and label them as either the
D or L form. Be sure to illustrate how you know it is the correct form.
Answer: A) 3; B) 23 = 8
C)

Diff: 3
Section: 6-3
Global: G2
LO: 6.3

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12) Identify the following (A-E) as enantiomer, epimer, or diastereoisomer of L-altrose:

A) B)

C) D) E)

Answer: A) enantiomer, B) epimer, C) epimer, D) epimer, E) diastereoisomer

Diff: 2
Section: 6-3
Global: G2
LO: 6.3

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13) A hemiacetal in an aldose is formed by the reaction between an ________ and an ________.
Answer: alcohol, aldehyde
Diff: 1
Section: 6-4
Global: G1
LO: 6.4

14) In the formation of a hemiacetal, the ________ group is converted into a hydroxyl group
when the ring is formed.
Answer: aldehyde
Diff: 2
Section: 6-4
Global: G1
LO: 6.4

15) In the beta anomer, the -OH on the anomeric carbon atom is ________ to carbon 6, meaning
on the ________ side of the ring.
Answer: cis, same
Diff: 2
Section: 6-4
Global: G1
LO: 6.4

16) In the pyranose form of D-glucose, the -OH group on the anomeric carbon atom in the α-
form is ________ to carbon 6, while in the β- form it is ________ to carbon 6.
Answer: trans, cis
Diff: 2
Section: 6-4
Global: G1
LO: 6.4

17) This molecule is the ________ anomer:

Answer: beta
Diff: 2
Section: 6-4
Global: G2
LO: 6.4

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18) Draw the Haworth and Fisher projections of α-D-galactose.
Answer:

Diff: 2
Section: 6-3, 6-4
Global: G2
LO: 6.3, 6.4

19) Draw the Fischer and Haworth projections for α-D-fructose.

Answer:

Diff: 2
Section: 6-3, 6-4
Global: G2
LO: 6.3, 6.4

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20) Draw the Fischer projection of D-glucose and identify the functional groups.
Answer:

A, aldehyde
B, primary alcohol
C, secondary alcohol
Diff: 2
Section: 6-2, 6-3
Global: G2
LO: 6.2, 6.3

21) In Benedict's test, a sugar that turns the initial blue color red is called a ________ sugar.
Answer: reducing
Diff: 1
Section: 6-4
Global: G1
LO: 6.4

22) In Benedict's test, the conversion of the blue color into red involves ________ of Cu2+ to
Cu+.
Answer: reduction
Diff: 1
Section: 6-4
Global: G1
LO: 6.4

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23) This molecule results from the ________ of an aldohexose.

Answer: reduction
Diff: 2
Section: 6-4
Global: G2
LO: 6.4

24) Two structures are possible when the ring is formed in a carbohydrate. These two forms are
called ________.
Answer: anomers
Diff: 1
Section: 6-4
Global: G1
LO: 6.4

25) In D-fructose, the four carbon atoms and an oxygen form a five-membered ring called a
________.
Answer: furanose
Diff: 1
Section: 6-4
Global: G1
LO: 6.4

26) The formation of a glycosidic bond is an example of condensation or hydrolysis?

Answer: condensation
Diff: 1
Section: 6-5
Global: G1
LO: 6.5

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27) Identify this glycosidic bond as alpha- or beta-:

Answer: alpha-
Diff: 1
Section: 6-5
Global: G2
LO: 6.5

28) Identify this glycosidic bond as alpha- or beta-:

Answer: beta-
Diff: 1
Section: 6-5
Global: G2
LO: 6.5

29) The following trisaccharide, computerose has just been discovered in nature.

A) What are the three monosaccharides that make up this trisaccharide?

B) Is this trisaccharide a reducing sugar? Why or why not?
C) What type of linkages connect the monosaccharides in this molecule?
Answer: A) Galactose, glucose, glucose; B) yes — it has a free open hemiacetal; C) Alpha 1→4
and Beta 1→4
Diff: 3
Section: 6-4, 6-5
Global: G2
LO: 6.3, 6.4, 6.5

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Test Bank for General, Organic, and Biological Chemistry, 4th Edition, Laura D. Frost

30) Describe the differences in the structures of the two polysaccharides that comprise starch.
Make sure you state their names and what type of linkage holds the monomer units together.
Answer: Amylose and amylopectin are the two components of starch.
Amylose — It is straight chains of glucose with α(1→4) linkages.
Amylopectin — It is branched chains of glucose with branches every 20-25 units, linkages are
α(1→4) and α(1→6).
Diff: 2
Section: 6-6
Global: G1
LO: 6.6

31) Draw the structure of acetylglucosamine.

Answer:

Diff: 2
Section: 6-6
Global: G2
LO: 6.6

32) Why is lettuce considered roughage and not an energy source for our bodies? What make its
components so different from other carbohydrate sources?
Answer: Lettuce is primarily made up of cellulose which is glucoses connected by β(1→4)
linkages. We do not have the necessary enzyme to break down this polysaccharide.
Diff: 2
Section: 6-6
Global: G2
LO: 6.6

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