Organic and Biochemistry for Today 8th

Edition Seager Solutions Manual

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Chapter 7: Carbohydrates
CHAPTER OUTLINE
17.1 Classes of Carbohydrates 17.4 Monosaccharides
17.2 The Stereochemistry of 17.5 Properties of Monosaccharides
Carbohydrates 17.6 Important Monosaccharides
17.3 Fischer Projections 17.7 Disaccharides 17.8 Polysaccharides

LEARNING OBJECTIVES/ASSESSMENT
When you have completed your study of this chapter, you should be able to:
1. Describe the four major functions of carbohydrates in living organisms. (Section 17.1; Exercise 17.2)
2. Classify carbohydrates as monosaccharides, disaccharides, or polysaccharides. (Section 17.1; Exercise
17.4)
3. Identify molecules possessing chiral carbon atoms. (Section 17.2; Exercise 17.8)
4. Use Fischer projections to represent D and L compounds. (Section 17.3; Exercise 17.12)
5. Classify monosaccharides as aldoses or ketoses, and classify them according to the number of carbon
atoms they contain. (Section 17.4; Exercise 17.22)
6. Write reactions for monosaccharide oxidation and glycoside formation. (Section 17.5; Exercise 17.34)
7. Describe uses for important monosaccharides. (Section 17.6; Exercise 17.37)
8. Draw the structures and list sources and uses for important disaccharides. (Section 17.7; Exercise
17.44)
9. Write reactions for the hydrolysis of disaccharides. (Section 17.7; Exercise 17.52)
10. Describe the structures and list sources and uses for important polysaccharides. (Section 17.8;
Exercise 17.54)

LECTURE HINTS AND SUGGESTIONS

1. Describe sugars as polyfunctional alcohols which can contain aldehyde or ketone groups. Explain
that many sugars are composed of two or more simple sugars linked together (Disaccharides and
polysaccharides). Depending on the student audience, it may be desirable to condense the material
somewhat and present some of it diagrammatically rather than using complete detailed structural
formulas.
2. Use everyday objects to demonstrate chirality. Hold up your two hands and show how they have a
mirror image relationship. Explain that the right hand is a mirror image of the left hand. Show that
they are similar but not identical. Be sure to emphasize the enantiomers (e.g., right and left-handed)
are real and not mirror images (they only have a mirror image relationship). Sometimes students get
confused and think we are speaking about images and not real objects (molecules). Emphasize that
everything has a mirror image and that we are speaking only of a special type of structural
relationship between two real objects (molecules). Explain the difference between capital "D and L"
and lower case "d and 1" to prevent confusion with material that they may encounter in other
courses. Explain that different systems are used for expressing stereochemical relationships and that
the D/L system is historically the earliest. It is a system useful for talking about carbohydrates and
amino acids because their relationship to D/L glyceraldehyde is fairly easy to establish.
3. The concept of reducing sugars can be illustrated by the simple test for glucose in the blood and urine
using Benedict's or Fehling's reagent. The test kits are readily available in drug stores and can be
easily used as a demonstration in the classroom.

415
416 Chapter 7

SOLUTIONS FOR THE END OF CHAPTER EXERCISES

CLASSES OF CARBOHYDRATES (SECTION 17.1)
17.1 The four important roles of carbohydrates in living organisms are: (1) to provide energy
through their oxidation, (2) to supply carbon for the synthesis of cell components, (3) to serve
as a stored form of chemical energy, and (4) to form a part of the structural elements of some
cells and tissues.

17. 2 a. cellulose – structural material in plants

b. sucrose, table sugar – an energy source in our diet
c. glycogen – form of stored energy in animals
d. starch – form of stored energy in plants

17.3 Monosaccharides are the simplest carbohydrates. Disaccharides contain two

monosaccharides. Polysaccharides contain many monosacharides.

17.4 a. table sugar – carbohydrate, e. cellulose – carbohydrate, polysaccharide

disaccharide
CH OH
2
b. OH – carbohydrate, f. – carbohydrate,
O
OH monosaccharide disaccharide
OH
OH

c. starch – carbohydrate, g. glycogen – carbohydrate, polysaccharide

polysaccharide
d. fructose – carbohydrate, h. amylose – carbohydrate, polysaccharide
monosaccharide

17.5 Carbohydrates are polyhydroxy aldehydes and ketones, or substances that yield such
compounds on hydrolysis. In other words, carbohydrates contain alcohol, aldehyde, and
ketone functional groups or will contain those functional groups upon hydrolysis.

THE STEREOCHEMISTRY OF CARBOHYDRATES (SECTION 17.2)

H O
17.6 Carbon atom 1 is not chiral because it is only bonded to three other
1C
atoms.
H 2C OH
Carbon atom 3 is not chiral because it is bonded to two hydrogen atoms.
3CH OH
2
Chiral carbon atoms are bonded to four unique groups.

17.7 The chiral carbon atom is marked with an

CH3 asterisk. The four attached groups are:
(1) a hydrogen atom,
CH2 CH NH2 (2) an amino group,
*
(3) a methyl group, and
CH2

(4) a group.

17.8 a. CH3CH2 CH CH2CH3 no chiral carbon atoms; no enantiomers

OH
 Carbohydrates 417
b. chiral O 1 chiral carbon atom;
2 stereoisomers; a pair of enantiomers
CH3CH2 CH C CH3

OH
c. chiral OH 1 chiral carbon atom; 2 stereoisomers;
a pair of enantiomers
C CH2CH3

CH3
17.9 a. 1 chiral carbon atom; 2 stereoisomers; a pair of
enantiomers

b. 1 chiral carbon atom;

2 stereoisomers; a pair of enantiomers

c. 1 chiral carbon atom;

2 stereoisomers;
a pair of enantiomers

FISCHER PROJECTIONS (SECTION 17.3)

CHO
17.10 The intersection of the lines represents a chiral carbon atom. The H and the OH
H OH groups (groups on horizontal bonds) stick out in front of the plane of the paper
and the CHO and CH2CH3 groups (groups on vertical bonds) stick out behind
CH2CH3
the plane of the paper.

17.11 a. L-form b. D-form

418 Chapter 7
17.12 a. D-form b. L-form
CH2OH CH2OH
CHO CHO

C O C O
HO H H OH

H OH HO H
HO H H OH

HO H H OH
H OH HO H

HO H H OH
CH2OH CH2OH

CH2OH CH2OH

COOH COOH COOH COOH

17.13 a. b.

H OH HO H H Cl Cl H

CH2OH CH2OH CH2OH CH2OH

D-form L-form D-form L-form

COOH COOH COOH COOH

17.14 a. b.
H NH2 H2N H H NH2 H2N H

CH3 CH3 CH2 CH2

D-form L-form
CH CH

CH3 CH3 CH3 CH3

D-form L-form

17.15 a. OH OH OH O b. OH O OH OH OH

CH2 CH CH C H CH2 C CH CH CH CH3

2 chiral carbon atoms; 4 stereoisomers 3 chiral carbon atoms; 8 stereoisomers

OH OH OH O OH OH OH OH
17.16 a. b.
CH2 CH CH C CH2 OH CH2 CH CH CH CHO
2 chiral carbon atoms; 4 stereoisomers 3 chiral carbon atoms; 8 stereoisomers

17.17 Aldoheptoses contain 5 chiral carbon atoms; therefore, 32 possible stereoisomers exist.
Sixteen of these stereoisomers are D form and sixteen of these stereoisomers are L form.

17.18 Aldopentoses contain 3 chiral carbon atoms; therefore, eight possible stereoisomers exist.
Four of these stereoisomers are D form and four of these stereoisomers are L form.

17.19 The study of chiral molecules is important in biochemistry because living organisms consist
largely of chiral substances. The stereochemistry of a biological compound plays a key role in
determining which receptors with which it will interact and enzymes will be able to catalyze
its reactions, as well as what its physiological effect on an organism will be.

17.20 Optically active molecules contain at least one chiral carbon atom, have nonsuperimposable
mirror images, and rotate the plane of polarized light.
 Carbohydrates 419
MONOSACCHARIDES (SECTION 17.4)
CHO CH2OH
17.21 a. b.
H OH C O

H OH H OH
aldohexose ketopentose
HO H
H OH

HO H
CH2OH

CH2OH

CH2OH CHO
17.22 a. b.
C O H OH

H OH ketopentose H OH aldopentose
HO H H OH

CH2OH CH2OH

CHO CH2OH
17.23 a. b.
HO H C O

H OH
HO H

CH2OH
An aldotetrose must have:
(1) –CHO at the top, (2) 4 total
carbon atoms, and (3) –CH2OH
at the bottom of the structure.
This aldotetrose has the L
configuration.
H OH
CH2OH
A ketopentose must have:
(1) a –CH2OH bonded to a carbonyl carbon
atom at the top, (2) 5 total carbon atoms, and
(3) a –CH2OH at the bottom of the structure.
This ketopentose has the D configuration.

PROPERTIES OF MONOSACCHARIDES (SECTION 17.5)

17.24 Certain carbohydrates are called sugars because they taste sweet.

17.25 Monosaccharides are soluble in water because they have many hydroxy groups and are able
to hydrogen bond to the water.

17.26
CHO

H OH

HO H The arrows indicate the sites on the molecule where water can
hydrogen bond to glucose.
H OH

H OH

CH2OH
420 Chapter 7
CH2OH CH2OH HOCH2 OH HOCH2 CH2OH
17.27 a. b.
OH O O
O O
OH OH CH2OH OH
OH OH OH OH
HO OH HO form
OH
OH
form

CH2OH CH2OH HOCH2 OH HOCH2

17.28 a. b.
OH OH OH
O O
O O
OH OH
OH
OH OH
OH
form
OH OH
form

17.29 CH2OH CH2OH

OH OH OH
O O
OH OH OH OH
-talose
OH -talose

CH2OH CH2OH
17.30
OH
O O
OH OH OH OH

OH OH -mannose OH -mannose

17.31 A pyranose ring refers to a carbohydrate which has a six-membered ring containing an
oxygen atom. A furanose ring refers to a carbohydrate which has a five-membered ring
containing an oxygen atom.

2+
17.32 When a sugar fails to react with Cu , it is a nonreducing sugar.

17.33 The cyclic compound β-D-galactose can react with Cu2+ and be classified as a reducing sugar
because as it undergoes mutarotation in solution, the ring opens, an aldehyde is formed, and
the compound can react with Benedict’s reagent, which is an oxidizing agent.

CHO COOH
17.34 a.
H OH H OH

H OH + Cu2+ H OH + Cu2O

H OH H OH

CH2OH CH2OH
 Carbohydrates 421
CH2OH CH2OH CH2OH
b.
OCH2CH3
O O O
2 + 2 CH3CH2 OH H+ + 2 H2O
OH OH + OH

HO OH HO OCH2CH3 HO
OH OH OH

HOCH2 OH HOCH2 OCH3 HOCH2 CH2OH

c. O O O
HO + HO HO
2 + 2 CH3 OH H + + 2 H2O

CH2OH CH2OH OCH3

OH OH OH

CH2OH HOCH2 CH2OH

17.35 a. b. HO
OCH2CH2CH3
O O
glycosidic
OH linkage
glycosidic
linkage OCH2CH3
HO
OH
OH

IMPORTANT MONOSACCHARIDES (SECTION 17.6)

17.36 Ribose and deoxyribose are monosaccharides used in the synthesis of nucleic acids.

17.37 D-glucose can be injected directly into the bloodstream to serve as an energy source because
glucose is the sugar transported by the blood to body tissues to satisfy energy requirements.
Glucose has a high solubility in aqueous solutions; it dissolves readily in water and in blood;
therefore, it poses no risks of toxicity itself and will not form dangerous solid occlusions in
the blood vessels.

17.38 Dextrose and blood sugar are two other names for D-glucose.

17.39 (b) Fructose is a ketohexose.

17.40 Glucose and galactose have similar structures. The only difference is the orientation of the
hydroxy group attached to carbon 4.

17.41 a. The natural sources of glucose are honey and fruits, as well as sucrose which is a
disaccharide containing glucose.
b. The natural source of fructose is fruit.
c. The natural source of galactose is milk, which contains the disaccharide lactose.

17.42 Fructose can be a low-calorie sweetener because it is sweeter, gram for gram, than the other
common sugars; consequently, less fructose is needed to obtain the same degree of sweetness.

DISACCHARIDES (SECTION 17.7)

17.43 Glucose is a component of sucrose, maltose, and lactose.

17.44 a. The most common household sugar sucrose

b. Formed during the digestion of starch maltose
c. An ingredient of human milk lactose
d. Found in germinating grain maltose
422 Chapter 7
e. Hydrolyzes when cooked with acidic foods to give invert sugar sucrose
f. Found in high concentrations in sugar cane sucrose

17.45 Glycosidic linkages are broken when disaccharides are hydrolyzed to monosaccharides.

17.46 The hemiacetal group of a lactose molecule is able to react with Benedict’s reagent because the
ring containing the hemiacetal group is not “locked.” In solution the hemiacetal group can
undergo mutarotation, opening the ring into an open-chain aldose that can react with
Bendict’s reagent.

17.47 Invert sugar is sweeter than sucrose because for every molecule of sucrose there are two
molecules of monosaccharides (glucose and fructose) in invert sugar and fructose is much
sweeter than sucrose.

17.48 Adding Benedict’s solution to a sample of the sweet-tasting water solution would provide a
qualitative test for the presence of sucrose or honey. Honey contains invert sugar that will
react with Benedict’s solution. Sucrose will not react with Benedict’s solution.

CH2OH CH2OH CH2OH

17.49 acetal hemiacetal
acetal
O
O O
OH
OH OH
O HO
HO OH OH
O
OH OH
and HOCH2 ketal
CH2OH CH2OH
acetal hemiacetal O
OH HO
O O
CH2OH
OH OH OH
O
HO
OH OH
Both and -maltose will be present because of
mutarotation in solution.

CH2OH
17.50 a. CH2OH
HO O
O
O OH
Lactose is a reducing sugar because it contains a
OH
OH
hemiacetal group.
OH
OH
CH2OH
b.
O

OH

HO
OH Sucrose is not a reducing sugar because it does not
O
contain a hemiacetal or a hemiketal group.
HOCH2

O
HO

CH2OH
OH

17.51 a. lactose β(1→4) glycosidic linkage

b. maltose α(1→4) glycosidic linkage
c. sucrose α1→ β2 glycosidic linkage
 Carbohydrates 423
17.52 a. When melibiose is hydrolyzed, glucose and galactose are the monosaccharides produced.
b. Melibiose is a reducing sugar because the glucose ring contains a hemiacetal group.
c. The glycosidic linkage in melibiose is an (1 6) linkage.

POLYSACCHARIDES (SECTION 17.8)

17.53 a. Contains both α(1→4) and α(1→6) glycosidic linkages amylopectin, glycogen
b. Is composed of glucose monosaccharide units amylose, amylopectin,
glycogen, cellulose
c. Contains acetal linkages between monosaccharide amylose, amylopectin,
units glycogen, cellulose
d. Is composed of highly branched molecular chains amylopectin, glycogen
e. Is composed of unbranched molecular chains amylose, cellulose
f. Contains only α(1→4) glycosidic linkages amylose
g. Contains only β(1→4) glycosidic linkages cellulose

17.54 a. The unbranched polysaccharide in starch amylose

b. A polysaccharide widely used as a textile fiber cellulose
c. The most abundant polysaccharide in starch amylopectin
d. The primary constituent of paper cellulose
e. A storage form of carbohydrates in animals glycogen

17.55 Celery is a good snack for people on a diet because it contains large amounts of cellulose,
which the human body cannot hydrolyze. Cellulose passes unchanged through the digestive
tract without contributing to the caloric value of food. Celery can fill a stomach without
providing many calories. It is also an excellent source of dietary fiber which combats
constipation and aids in the elimination of body wastes, flushing the body of toxins.

ADDITIONAL EXERCISES
17.56 Maltose (C12H22O11) has approximately twice the mass per molecule of glucose (C 6H12O6);
therefore if two 10% (w/v) solutions are made with maltose and glucose as solutes, the
maltose solution would contain roughly half the number of molecules contained in the
glucose solution. Neither of the solutes dissociates in water since both are molecular. The
boiling point of a solution increases with the number of solute particles in solution; therefore,
the glucose solution would contain more molecules of solute and would have the higher
boiling point.

17.57 One mole of D-glucose only reacts with one mole of methanol to form an acetal because the
pyranose ring already contains one –OR group.

17.58 1 mole sucrose 1 mole glucose 180 g glucose

100 g sucrose
342 g sucrose 1 mole sucrose 1 mole glucose
52.6 g glucose

17.59 Glucose is a solid at room temperature because it is able to form many hydrogen bonds per
molecule (the ratio of oxygen to carbon is one to one) and it has a high molecular weight. The
combination of a high degree of hydrogen bonding with fairly strong dispersion forces causes
it to be a solid at room temperature. Hexanal and 1-hexanol each contain one oxygen atom
per six carbon atoms and a relatively low molecular weight. Hexanal cannot hydrogen bond
amongst its own molecules. It primarily experiences dipolar forces between its molecules.
424 Chapter 7
Since this is a much weaker intermolecular force than the hydrogen bond, it will have a lower
boiling and melting point than glucose. 1-Hexanol can hydrogen bond, but makes fewer
hydrogen bonds per molecule than glucose. This, combined with its weaker dispersion
forces, causes it to be a liquid at room temperature.

17.60 If maltose was used in the “Osmosis through carrot membranes” demonstration and the
solution level rose 5 cm above the carrot in the tube and then maltase was added to the
solution, the solution level in the tube would further increase. Adding maltase would cause
each maltose molecule to split into two molecules of glucose, which would double the
osmolarity of the original maltose solution and cause the water level in the tube to further
increase.

ALLIED HEALTH EXAM CONNECTION

17.61 Glucose and fructose are (b) isomers because they have the same molecular formula, but
different structural formulas and (c) hexoses because they are carbohydrates that contain six
carbon atoms.

17.62 (a) Cellulose, (b) starch, and (d) glycogen are composed of long chains of glucose molecules.
(c) Cholesterol is not composed of glucose molecules.

17.63 a. dextrose monosaccharide

b. fructose monosaccharide
c. sucrose disaccharide – glucose and fructose monosaccharides
d. maltose disaccharide – 2 glucose monosaccharides
e. lactose disaccharide – glucose and galactose monosaccharides
f. ribose monosaccharide

17.64 Hydrolysis is the general type of reaction used to decompose sucrose to glucose and fructose.

17.65 The Cu2+ is reduced during the reaction of Benedict’s reagent with glucose. The oxidation
number on copper changes from +2 to +1 during the reaction, which means the copper ion
gains an electron and is reduced.

17.66 (c) Glycogen is the polysaccharide that is a branched polymer of glucose found in the liver
and muscle cells.

CHEMISTRY FOR THOUGHT

17.67 Genetically altering human intestinal bacteria so that they could hydrolyze the linkages of
cellulose would allow humans to digest this plant material for use as an energy source. This
genetic change would compromise the ability of humans to eat plant matter for roughage,
which is needed to provide bulk, stimulate contraction of the intestines, and aid in the
passage of food through the digestive system. Since a wide variety of foods are currently
available for energy and cellulose plays an important role in digestion, this genetic
modification would not be beneficial for most humans.

17.68 2.80 105 u 1 molecule linked glucos e

1 molecule starch 171 u linked glucos e
1.64 103 glucos e molecules
 Carbohydrates 425
Note: The molecular mass of glucose is 180 u, but when glucose links together to form a
molecule of starch, 1 molecule of water (18.0 u) is lost for every two glucose units or 0.5
molecules of water per glucose unit; therefore, the molecular mass of a linked glucose unit is
180-9.0 = 171 u.

17.69 The open-chain form of glucose constitutes only a small fraction of any glucose sample, yet
when Cu2+ is used to oxidize the open-chain form, nearly all the glucose in a sample reacts.
The reason this occurs is that the open-chain form of glucose is in equilibrium with the ring
forms of glucose and as the open-chain form of glucose reacts with the Cu2+ it is essentially
removed from the equilibrium; consequently, in an attempt to reestablish equilibrium, the
ring forms of glucose undergo mutarotation to produce the open-chain form of glucose,
which in turn reacts with the Cu2+ and causes more of the ring forms of glucose to undergo
mutarotation. This cycle continues until nearly all of the glucose in a sample reacts with the
Cu2+. This is an example of Le Châtelier’s principle.

17.70 Aspartame (Nutrasweet) contains calories and yet is used in diet drinks. A drink can contain
aspartame as a sweetener and yet be low in calories because the amount needed to sweeten a
diet drink is so small that very few calories are added to the drink.

17.71 When lactose in cow’s milk is hydrolyzed in a child’s digestive system, 1 molecule of
galactose and 1 molecule of glucose are produced for each molecule of lactose.

17.72 Foods that would be expected to give a positive starch test include bread, crackers, pasta, and
rice.

17.73 Unlike the coiled form of amylose which reacts with iodine by incorporating the iodine
molecules into its structure to produce a positive bluish-black iodine test, amylopectin has a
branched structure that cannot incorporate iodine into its structure, and consequently, when
amylopectin is tested in its pure form it has a negative iodine test.

17.74 Amylose is a straight-chain glucose polymer similar to cellulose. Paper manufactured with
amylose instead of cellulose would have less longevity because amylose forms loose spiral
structures unlike cellulose which forms extended straight chains that can be aligned side by
side to form well-organized, water-insoluble fibers in which the hydroxy groups form
numerous hydrogen bonds with the neighboring chains that confer rigidity and strength to
the overall structure of the paper.

17.75 Raffinose contains three monosaccharide components, galactose, glucose, and fructose.
Disregarding the types of linkages, there are six possible structures for raffinose because each
of the monosaccharides could be the central monosaccharide to which each of the other
monosaccharides was bonded.

EXAM QUESTIONS
MULTIPLE CHOICE
1. Which of the following choices is a carbohydrate?
a. progestin b. formaldehyde c. galactose d. hexamide

Answer: C
426 Chapter 7
2. Which of the following is NOT a polysaccharide?
a. amylopectin c. glycogen
b. deoxyribose d. cellulose

Answer: B

3. Which of the following groups are expected to be found in carbohydrates?

a. alcohol b. thiol c. methyl d. amide

Answer: A

4. What characteristic of carbohydrates is not commonly found in the previously studied classes of
compounds?
a. Carbohydrates are unique in that they do not contain any nitrogen.
b. Carbohydrates often contain a functional group on each carbon.
c. The carbohydrate class is the only class composed solely of cyclic compounds.
d. There is more than one correct response.
Answer: B

5. The simplest carbohydrates are called:

a. monosaccharides. c. polysaccharides.
b. disaccharides. d. oligosaccharides.
Answer: A

6. Carbohydrates which contain two sugar units chemically linked together are called:
a. monosaccharides. c. trisaccharides.
b. disaccharides. d. polysaccharides.
Answer: B

7. Which of the following is a disaccharide?

a. glucose b. fructose c. galactose d. maltose
Answer: D

8. What is a short description of an enantiomer?

a. Enantiomers are all of the isomers for compounds that can have in excess of two isomers.
b. Enantiomers are those compounds that can have two isomers that are straight chain and
the right side is different from the left side.
c. Enantiomers are compounds which are nonsuperimposable mirror images of each other.
d. There is more than one correct response.
Answer: C

9. Which of the following statements about chiral carbons is correct?

a. A chiral carbon is one that has four different groups attached.
b. A chiral carbon is one that determines the possibility of stereoisomerism.
c. A chiral carbon can be an interior carbon.
d. There is more than one correct response.
Answer: D
 Carbohydrates 427
10. Which of the following can exist as enantiomers?
a. O c. O

CH3 CH2 CH2 C H CH3 CH C H

CH3
b. O d. all of the above

CH3 CH2 CH C H

CH3
Answer: B

O OH OH
11. Which of the carbon atoms in the following
structure are correctly called chiral carbon
HO CH2 C CH CH CH2 OH
atoms? 1 2 3 4 5
a. carbons 1 and 5 c. carbons 2, 3 and 4
b. carbons 3 and 4 d. carbons, 1, 2, 3, 4, and 5
Answer: B
CH2 OH

C O

H C OH

H C OH

12. How many chiral carbons are contained in the compound, CH2 OH ?
a. 1 b. 2 c. 3 d. 4
Answer: B
CH2 OH

C O

H C OH

H C OH

H C OH

13. How many chiral carbons are contained in ribose, shown alongside? CH2 OH
a. 1 b. 2 c. 3 d. 4
Answer: C
428 Chapter 7
CHO

H OH

14. The structure CH2OH has the:

a. a D configuration. b. an L configuration. c. neither D nor L d. both D and L
configuration. configurations.
Answer: A
CHO

H OH

HO H

15. The structure CH2OH has the:

a. a D configuration. b. an L configuration. c. neither D nor L d. both D and L
configuration. configurations.
Answer: B
O

C H

H C OH

H C OH

16. Which of the following compounds is the enantiomer of the compound, CH2 OH ?
O b. O c. O d. O
a.
C H C H C H C H

H C OH HO C H HO C H H C OH

HO C H HO C H H C OH H C OH

CH2 OH CH2 OH CH2 OH CH2 OH

Answer: B

17. Which form of monosaccharides is/are preferred by human cells?

a. D c. both D and L
b. L d. neither D nor L
Answer: A
 Carbohydrates 429
CH2 OH

C O

HO C H

HO C H

18. The carbohydrate CH2 OH may be classified as:

a. an aldopentose. c. a ketopentose.
b. an aldohexose. d. a ketohexose.
Answer: C

19. Which of the following monosaccharides is a ketohexose?

a. ribose b. glucose c. galactose d. fructose
Answer: D

20. How many stereoisomers of an aldopentose exist?

a. 2 b. 4 c. 6 d. 8
Answer: D

21. Of the 16 aldohexoses, how many exist in the D form?

a. 8 b. 16 c. 4 d. 6
Answer: A

22. The sweetest of the common sugars is:

a. fructose. b. glucose. c. galactose. d. maltose.
Answer: A

23. The cyclic form of glucose results from the formation of:
a. an ester. c. a hemiacetal.
b. an acetal. d. an amide.
Answer: C

24. The cyclic form of glucose has how many possible stereoisomers compared to the noncyclic form?
a. double c. reduced by one-half
b. triple d. remains the same
Answer: A

25. The cyclic form of _____ contains a furanose ring.

a. glucose b. maltose c. galactose d. fructose
Answer: D

26. Sugars which contain an aldehyde group that can be oxidized are called:
a. reducing sugars. c. glycosides.
b. oxidizing sugars. d. simple sugars.
Answer: A
430 Chapter 7
27. Of the monosaccharides, which is the most important nutritionally?
a. ribose b. glucose c. galactose d. fructose
Answer: B

28. A monosaccharide used to form nucleic acids is:

a. glucose. b. galactose. c. ribose. d. maltose.
Answer: C

29. A carbohydrate present in the blood is:

a. sucrose. b. glucose. c. fructose. d. maltose.

Answer: B

30. A sugar present in honey in a 1:1 ratio with glucose is:

a. fructose. b. maltose. c. sucrose. d. galactose.

Answer: A

31. A component of lactose is the sugar:

a. ribose. b. deoxyribose. c. fructose. d. galactose.
Answer: D

32. The linkage between the two monosaccharide units of a disaccharide is a(n):
a. hemiacetal linkage. c. ester linkage.
b. alpha linkage. d. glycosidic linkage.
Answer: D

33. Which of the following sugars fails to give a positive Benedict's test?
a. glucose b. galactose c. lactose d. sucrose
Answer: D

34. Which of the following carbohydrates yields invert sugar upon hydrolysis?
a. fructose b. sucrose c. starch d. glycogen

Answer: B

35. The disaccharide formed during the digestion of starch is:

a. amylase. b. lactose. c. maltose. d. sucrose.
Answer: C

36. Maltose upon hydrolysis yields:

a. glucose and galactose. c. only glucose.
b. glucose and fructose. d. nothing; hydrolysis does not occur.
Answer: C

37. The body stores carbohydrates as:

a. cellulose. b. glycogen. c. sucrose. d. starch.
Answer: B
 Carbohydrates 431
38. A polysaccharide containing (1 4) linkages is:
a. cellulose. b. glycogen. c. amylose. d. amylopectin.
Answer: A

39. Structurally, glycogen is most similar to:

a. amylose. b. amylopectin. c. cellulose. d. sucrose.
Answer: B

40. Which polysaccharide usually makes up 80-90% of plant starch?

a. chitin c. heparin
b. amylopectin d. hyaluronic acid
Answer: B

41. What is the major difference between glucose and sorbitol?

a. Glucose has 6 carbons; sorbitol has 5 carbons.
b. Glucose has 6 carbons; sorbitol has 7 carbons.
c. Glucose contains hydroxy groups; sorbitol does not contain hydroxy groups.
d. Glucose contains an aldehyde carbon; sorbitol has an alcohol carbon in that location.
Answer: D
CH2OH OH
O

42. The stucture OH OH is shown in which anomeric form?

a. b. c. cis d. trans
Answer: B
CH2OH
O

OH

43. The struture OH OH is shown in which anomeric form?

a. b. c. cis d. trans
Answer: A
432 Chapter 7
CH2OH CH2OH

O O

O
OH OH

44. The structure OH OH OH OH

has which type of glycosidic linkage?
a. b. c. d. (1 4)
Answer: D
CH2OH

O
CH2OH

O
O
OH

OH OH
OH

45. The structure OH OH

has which type of glycosidic linkage?
a. b. c. d. (1 4)
Answer: B

46. Artificial sweeteners should be avoided by people suffering from phenylketonuria (PKU) due to their
body’s inability to metabolize __________ properly.
a. aldehydes c. ketones
b. phenols d. phenylalanine
Answer: D

47. Monosaccharides and disaccharides both have a sweet taste. What taste does a polysaccharide have?
a. sweet c. bitter
b. sour d. tasteless
Answer: D

48. Many commercials sell fiber supplements but you do not have the money to buy them. Which of the
following is not a good source of fiber?
a. steak c. carrots
b. beans d. banana
Answer: A
 Carbohydrates 433

TRUE-FALSE
1. Carbohydrates have their name because the ratio of carbon to water is always 1:1.
Answer: F

2. A characteristic of carbohydrates is that a carbonyl carbon is usually incorporated in their structures.

Answer: T

3. Molecules that are nonsuperimposable mirror images are enantiomers.

Answer: T

4. In order for molecules to be nonsuperimposable mirror images, there must be at least one atom that
does not have duplicate groups attached.
Answer: T

5. A molecule with 3 chiral atoms would have 6 stereoisomers.

Answer: F

6. There is no biological significance attributed to stereoisomers.

Answer: F

7. One of the characteristics of organic molecules is that they all can exist as stereoisomers.
Answer: F

8. CH4 could exist as a pair of enantiomers.

Answer: F

9. sec-Butyl alcohol has two stereoisomers.

Answer: T

10. Polysaccharides tend to be very sweet.

Answer: F

11. Polysaccharides usually give a negative Benedict's test.

Answer: T

12. Starch is made up of 50 to 100 glucose units.

Answer: F

13. Cellulose does not contribute to the caloric intake in humans.

Answer: T

14. Cellulose is a polysaccharide composed of glucose units.

Answer: T

15. The hydrolysis of cellulose and starch would give the same monosaccharide.
Answer: T

16. One function of carbohydrates is to form structural elements of some cells and tissues.
Answer: T
434 Chapter 7
17. All aldopentoses have 5 carbon atoms.
Answer: T

18. All sugars have ketoses.

Answer: F

19. The L form of a monosaccharide has an -OH on the left on the chiral carbon furthest from the
carbonyl group in the Fischer projection.
Answer: T

20. The two forms of the glucose ring resulting from the substituents on the C-1 carbon are anomers.
Answer: T