Solution Manual for General, Organic, and Biological

Chemistry, 2/E 2nd Edition : 0321802632

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Solution Manual for General, Organic, and Biological Chemistry, 2/E 2nd Edition : 0321802632

Carbohydrates—Life’s Sweet Molecules

Chapter 6 integrates the functional groups alcohol, aldehyde, and ketone into the context of

carbohydrates to illustrate relevant structure, bonding, and chirality. Students are introduced to

Fischer projections and diastereomers using carbohydrates as examples. Several of the reactions

introduced in Chapter 5 are applied here to carbohydrates including oxidation–reduction, and

condensation/hydrolysis. The ring formation of carbohydrates serves as the focus of hemiacetal

formation reactions and leads to a consideration of the Haworth projections. Glycoside formation

as a condensation reaction and the naming of glycosidic bonds introduce important

disaccharides. The chapter continues with some important polysaccharides and concludes with

treatment of relevant blood carbohydrates, the ABO blood groups, and heparin.

Chapter Outline

6.1 Classes of Carbohydrates

Integrating Chemistry: Fiber in Your Diet

6.2 Functional Groups in Monosaccharides

Discovering the Concepts: Fischer Projections

6.3 Stereochemistry in Monosaccharides

Solving a Problem: Drawing an Enantiomer in a Fischer Projection

Discovering the Concepts: Ring Formation

6.4 Reactions of Monosaccharides

Solving a Problem: Drawing Pyranose Rings from Linear Monosaccharides

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6.5 Disaccharides

Integrating Chemistry: Relative Sweetness of Sugars and Artificial Sweeteners

6.6 Polysaccharides

6.7 Carbohydrates and Blood

Integrating Chemistry: Universal Donors and Acceptors

Integrating Chemistry: Heparin

Learning Outcomes

Section 6.1: Classes of Carbohydrates

• Classify carbohydrates as mono-, di-, oligo-, or polysaccharides.
• Distinguish soluble and insoluble fiber.

Section 6.2: Functional Groups in Monosaccharides

• Distinguish primary, secondary, and tertiary alcohols.
• Recognize and draw the functional groups alcohol, aldehyde, and ketone.

Section 6.3: Stereochemistry in Monosaccharides

• Distinguish D- and L- stereoisomers of monosaccharides.
• Draw Fischer projections of linear monosaccharides.
• Define enantiomer, epimer, and diastereomer.
• Draw enantiomers and diastereomers of linear monosaccharides.
• Characterize common monosaccharides.

Section 6.4: Reactions of Monosaccharides

• Draw the cyclic α and β anomers from linear monosaccharide structures.
• Draw oxidiation and reduction products of aldoses.

Section 6.5: Disaccharides

• Locate and name glycosidic bonds in disaccharides.
• Distinguish condensation and hydrolysis reactions of simple sugars.
• Characterize common dissacharides.

Section 6.6: Polysaccharides

• Identify polysaccharides by glycosidic bond and sugar subunit.

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Section 6.7: Carbohydrates and Blood
• Predict ABO compatibility.
• Describe the structure and role of heparin.

Laboratory Suggestions

• Lab 8A: What Happens to Bananas as They Ripen?

• Lab 8B: Can We Control the Ripening of Bananas?
• Lab 13: Where Is Lactose Digested?

Chapter 6
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Answers to Problems
Practice Problems
6.1 a. polysaccharide b. oligosaccharide c. disaccharide
6.2 a. oligosaccharide b. polysaccharide c. monosaccharide

6.3 a. secondary b. primary c. tertiary

d. secondary

6.4 a. tertiary b. secondary c. primary

d. secondary

6.5 a. ketone b. ketone c. aldehyde

6.6 a. ketone b. aldehyde c. ketone

6.7 a. D-isomer b. L-isomer c. D-isomer

6.8 a. D-isomer b. L-isomer c. D-isomer

6.9

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6.10 a. b.

6.11 A—diastereomer; B—diastereomer; C—enantiomer

6.12 A—diastereomer; B—enantiomer; C—diastereomer

6.13 a. D-glucose b. D-fructose c. D-mannose

6.14 a. D-galactose b. D-glucose c. D-fructose

6.15 a. beta b. beta

6.16 a. beta b. alpha

6.17

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6.18

6.19 carboxylic acid

6.20 alcohol

6.21

6.22 a. b.

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6.23 a. condensation b. condensation c. hydrolysis

6.24 a. hydrolysis b. condensation c. hydrolysis

6.25  (1→3)

6.26  (1→6)

6.27

6.28
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6.29 a. sucrose b. lactose c. maltose d. lactose

6.30 a. sucrose b. maltose c. lactose d. sucrose

6.31 a. Both contain  (1 → 4 ) glycosidic bonds and only D-glucose. Amylopectin also
contains branching  (1 → 6 ) .

b. Both contain  (1 → 4 ) glycosidic bonds and branching  (1 → 6 ) and only D-glucose.

Branching occurs more often in glycogen than amylopectin.

6.32 a. Both are linear polysaccharides composed entirely of glucose. In amylose, the
glycosidic linkages are  (1 → 4 ) , but in cellulose, they are  (1 → 4 ) .

b. Both are linear polysaccharides with  (1 → 4 ) glycosidic bonds. Cellulose contains

glucose and chitin contains N-acetylglucosamine.

6.33 a. cellulose, chitin

b. amylose, amylopectin

c. amylose

d. glycogen

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6.34 a. glycogen

b. chitin, cellulose

c. amylopectin

d. amylose, glycogen

6.35 a. No. A person with type B blood can only receive type B or O blood.

b. No. A person with type B blood can only receive type B or O blood.

6.36 a. No. A person with type O blood can only receive type O blood.

b. No. A person with type O blood can only receive type O blood.

Additional Problems

6.37 C4 H8O4

6.38 C5 H10O5

6.39 An oligosaccharide is smaller, containing between three and nine monosaccharide units,
while a polysaccharide contains 10 or more monosaccharide units.

6.40 A monosaccharide is a simple sugar containing three or more carbons. A disaccharide is

composed of two monosaccharides joined through a glycosidic bond.

6.41 Soluble fibers mix with water and form a gel-like substance that gives a feeling of
fullness when eaten.

6.42 Insoluble fibers are dietary carbohydrates that do not dissolve in water and move through
the digestive tract unchanged. Insoluble fiber is important for a healthy digestive tract.

6.43 aldehyde, hydroxyls (alcohol)

6.44 ketone, hydroxyls (alcohol)

6.45 a. secondary b. primary c. secondary

d. primary e. secondary

6.46 a. primary b. primary c. secondary

d. tertiary e. secondary

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6.47 a. enantiomer b. epimer

6.48 a. structural isomers b. diastereomers

6.49 a. alpha b. beta

6.50 a. beta b. alpha

6.51

6.52

-D-fructose -D-fructose

6.53

6.54
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6.55

6.56

Talose reduced at C1.

6.57 a. yes b. yes c. no d. no

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6.58 a. yes b. yes c. yes d. no

6.59

6.60

 (1→4) glycosidic bond

6.61

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6.62 Cellulose is an insoluble fiber, which has a laxative effect and adds bulk to the diet.
Cellulose assists with digestive movement in the small and large intestine, thus helping to
prevent constipation.

6.63 a. sucrose b. glucose c. L-fucose

d. amylose, amylopectin e. chitin

6.64 a. maltose b. fructose c. heparin

d. glycogen e. cellulose

6.65 a. no b. no

6.66 a. no b. yes

Challenge Problems

6.67

6.68

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Solution Manual for General, Organic, and Biological Chemistry, 2/E 2nd Edition : 0321802632

6.69

c. Splenda is not a reducing sugar.

6.70 Amylopectin. The amylase enzyme works from the non-reducing end of the polysaccharide.
Amylopectin, with its many branches, has many ends for the amylase to work from.

6.71 200 calories; 9%

6.72

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