1. Chapter 14 Carbohydrates
14.1
Carbohydrates
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2. Carbohydrates Carbohydrates are
A major source of energy from our diet.
Composed of the elements C, H, and O.
Also called saccharides, which means “sugars.”
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3. Carbohydrates Carbohydrates Are produced by photosynthesis in plants.
Such as glucose are synthesized in plants from CO2, H2O, and energy from the sun.
Are oxidized in living cells (respiration) to produce CO2, H2O, and energy.
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4. Types of Carbohydrates
The types of carbohydrates are
Monosaccharides, the simplest carbohydrates.
Disaccharides, which consist of two monosaccharides.
Polysaccharides, which contain many monosaccharides.
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5. Monosaccharides Monosaccharides consist of
3 to 6 carbon atoms, typically.
A carbonyl group (aldehyde or ketone).
Several hydroxyl groups.

6. Aldoses Aldoses are monosaccharides With an aldehyde group. O ║
With many hydroxyl (─OH) groups.
triose (3 C atoms)
tetrose (4 C atoms)
pentose (5 C atoms)
hexose (6 C atoms) O ║
C─H aldose │
H─ C─OH
CH2OH
Erythose, an aldotetrose

7. Ketoses Ketoses are monosaccharides CH2OH With a ketone group.
With many hydroxyl (─OH) groups.
triose (3 C atoms)
tetrose (4 C atoms)
pentose (5 C atoms)
hexose (6 C atoms)
CH2OH │
C=O ketose
H─ C─OH
H─C─OH
Fructose, a ketohexose

8. Learning Check
Identify each as aldo- or keto- and as tetrose, pentose,
or hexose:
A B

9. Solution
A. aldohexose
B. ketopentose

10. Structures of Monosaccharides
14.2
Structures of Monosaccharides
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11. Fischer Projections A Fischer projection
Is used to represent carbohydrates.
Places the most oxidized group at the top.
Shows chiral carbons as the intersection of vertical and horizontal lines.
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12. D and L Notations In a Fischer projection, the −OH group on the
Chiral carbon farthest from the carbonyl group determines an L or D isomer.
Left is assigned the letter L for the L-isomer.
Right is assigned the letter D for the D-isomer.
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13. Examples of D and L Isomers of Monosaccharides
D-glucose D-ribose L-galactose

14. Learning Check Identify each as the D or L isomer. A. B. C.
__-ribose __- threose __- fructose

15. Solution Identify each as the D or L isomer. A. B. C.
L-ribose L-threose D-fructose

16. D-Glucose D-glucose is Found in fruits, corn syrup, and honey.
An aldohexose with the formula C6H12O6.
Known as blood sugar in the body.
The monosaccharide in polymers of starch, cellulose, and glycogen.
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17. Blood Glucose Level In the body,
Glucose has a normal blood level of mg/dL.
A glucose tolerance test measures blood glucose for several hours after ingesting glucose.
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18. D-Fructose D-fructose Is a ketohexose C6H12O6.
Is the sweetest carbohydrate.
Is found in fruit juices and honey.
Converts to glucose in the body.
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19. D-Galactose D-galactose is An aldohexose C6H12O6.
Not found free in nature.
Obtained from lactose, a disaccharide.
A similar structure to glucose except for the
–OH on C4.

20. Learning Check
Draw the structure and Fischer projection of D-fructose.

21. Solution
CH2OH │
C=O
HO H
H OH
Fischer projection

22. Cyclic Structures of Monosaccharides
14.3
Cyclic Structures of Monosaccharides
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23. Cyclic Structures Cyclic structures
Are the prevalent form of monosaccharides with 5 or 6 carbon atoms.
Form when the hydroxyl group on C-5 reacts with the aldehyde group or ketone group.

24. Cyclic Haworth Structures
Stable cyclic hemiacetals form
When the C=O group and the
—OH are part of the same molecule.
For hexoses, the hydroxyl group on C-5 reacts with the aldehyde group or ketone group.
The cyclic structure of a D-isomer has the last CH2OH group located above the ring.

25. Drawing the Cyclic Structure for Glucose
STEP 1 Number the carbon chain and turn clockwise to form a linear open chain. 1 2 3 4 5 6

26. Cyclic Structure for Glucose
STEP 2 Bend the chain to make a hexagon
Bond the C5 –O– to C1.
Place the C6 group above the ring.
Write the –OH groups on C2 and C4 below the ring.
Write the –OH group on C3 above the ring.
Write a new –OH on C1. 6 5

27. Cyclic Structure for Glucose (cont)
STEP 3 The new –OH on C1 is drawn
Down for the  anomer.
Up for the  anomer.  
-D-glucose -D-glucose

28. Summary of the Formation of Cyclic Glucose
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29. -D-Glucose and β-D-Glucose in Solution
When placed in solution,
Cyclic structures open and close.
-D-glucose converts to β-D-glucose and back.
There is only a small amount of open chain.
-D-glucose D-glucose (open) β-D-glucose
(36%) (trace) (64%)

30. Cyclic Structure of Fructose
Is a ketohexose.
Forms a cyclic structure.
Reacts the —OH on C-5 with the C=O on C-2.
α-D-fructose
D-fructose
-D-fructose

31. Learning Check
Write the cyclic form of -D-galactose

32. Solution
-D-galactose

33. Chemical Properties of
14.4
Chemical Properties of
Monosaccharides
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34. Reducing Sugars Reducing sugars
Are monosaccharides with a carbonyl group that oxidizes to give a carboxylic acid.
Undergo reaction with Benedict’s reagent (Cu2+) to give the corresponding carboxylic acid.
Include the monosaccharides glucose, galactose, and fructose.

35. Oxidation of D-Glucose
Glucose is oxidized to a carboxylic acid
Benedicts reagent
[O]
Cu+ (reduced form)
Glucose is a reducing sugar

36. Reduction of Monosaccharides
D-Glucitol
The reduction of monosaccharides
Involves the carbonyl group.
Produces sugar alcohols called alditols.
Such as D-glucose gives D-glucitol also called sorbitol.
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37. Learning Check Write the products of the oxidation and reduction of
D-mannose.
D-mannose

38. Solution Write the products of the oxidation and reduction of
D-mannose.
D-mannitol D-mannose D-mannonic acid

39. 14.5 Disaccharides Copyright © 2007 by Pearson Education, Inc.
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40. Important Disaccharides
A disaccharide
Consists of two monosaccharides.
Monosaccharides Disaccharide
Glucose + glucose maltose + H2O
Glucose + galactose lactose + H2O Glucose + fructose sucrose + H2O

41. Maltose Maltose is A disaccharide also known as malt sugar.
Composed of two D-glucose molecules.
Obtained from the hydrolysis of starch.
Linked by an -1,4-glycosidic bond formed from the
 −OH on C1 of the first glucose and −OH on C4 of the second glucose.
Used in cereals, candies, and brewing.
Found in both the - and β - forms.

42. Formation of Maltose Copyright © 2007 by Pearson Education, Inc.
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43. Lactose
Lactose
Is a disaccharide of β-D-galactose and α- or β-D-glucose.
Contains a β -1,4-glycosidic bond.
Is found in milk and milk products.
α-form
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44. Sucrose Sucrose or table sugar
Is obtained from sugar cane and sugar beets.
Consists of α-D-glucose and β-D-fructose..
Has an α,β-1,2-glycosidic bond.
α-D-glucose
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β-D-fructose

45. Learning Check Write the structures and names of the two
monosaccharides that form when sucrose is
hydrolyzed.

46. Solution
α-D-glucose
β-D-fructose

47. Sweeteners Sugars and artificial sweeteners Differ in sweetness.
Are compared to sucrose (table sugar), which is assigned a value of 100.
TABLE 15.2
60 000

48. Learning Check Identify the monosaccharides in each of the following:
A. lactose
(1) α-D-glucose (2) β-D-fructose (3) β-D-galactose
B. maltose
(1) α-D-glucose (2) β-D-fructose (3) β-D-galactose
C. sucrose
(1) α-D-glucose (2) β-D-fructose (3) β-D-galactose

49. Solution Identify the monosaccharides in each of the following:
A. lactose
(1) α-D-glucose (3) β-D-galactose
B. maltose
(1) α-D-glucose
C. sucrose
(1) α-D-glucose (2) β-D-fructose

50. 14.6 Polysaccharides Copyright © 2007 by Pearson Education, Inc.
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51. Polysaccharides Polysaccharides Are polymers of D-glucose.
Include amylose and amylopectin, starches made of α-D-glucose.
Include glycogen (animal starch in muscle), which is made of α-D-glucose.
Include cellulose (plants and wood), which is made of
β-D-glucose.
α-D-glucose

52. Structures of Amylose and Amylopectin
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53. Amylose Amylose is A polymer of α-D-glucose molecules.
Linked by -1,4 glycosidic bonds.
A continuous (unbranched) chain.
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54. Amylopectin Amylopectin Is a polymer of α-D-glucose molecules.
Is a branched-chain polysaccharide.
Has α-1,4-glycosidic bonds between the glucose units.
Has α-1,6 bonds to branches.
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55. Glycogen
Glycogen
Is the polysaccharide that stores α-D-glucose in muscle.
Is similar to amylopectin, but is more highly branched.
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56. Cellulose
Cellulose
Is a polysaccharide of glucose units in unbranched chains.
Has β-1,4-glycosidic bonds.
Cannot be digested by humans because humans cannot break down β-1,4-glycosidic bonds.
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57. Learning Check Identify the polysaccharides and types of glycosidic
bonds in each of the following:
A. B. C.

58. Solution A. Cellulose -1,4-glycosidic bonds
B. Amylose -1,4-glycosidic bonds
Amylopectin -1,4-and -1,6-glycosidic bonds
C. Glycogen -1,4-and -1,6-glycosidic bonds
(more branched than amylopectin)