Chapter 24 Exam Prep Carbohydrates

Organic Chemistry, 4e (Klein)

Chapter 24 Carbohydrates

1) Plants convert carbon dioxide and water into glucose in the presence of sunlight via ________.

A) hydrolysis

B) retrosynthesis

C) the Killiani synthesis

D) photosynthesis

E) none of these

Diff: 1

Learning Objective: 24.1 Describe the structural features of carbohydrates

2) Carbohydrates are ________.

A) polyhydroxy esters

B) polyhydroxy aldehydes

C) polyhydroxy ketones

D) polyhydroxy alkanes

E) B and C

Diff: 1

Learning Objective: 24.1 Describe the structural features of carbohydrates

3) Simple sugars are called ________, a term that derives from the Latin word for sugar, saccharum.

A) monosaccharides

B) disaccharides

C) polysaccharides

D) saccharides

E) all of these

Diff: 1

Learning Objective: 24.2 Describe how monosaccharides are classified

4) Polysaccharides are made by joining ________ together.

A) disaccharides

B) trisaccharides

C) polysaccharides

D) monosaccharides

E) all of these

Diff: 1

Learning Objective: 24.2 Describe how monosaccharides are classified

5) A monosaccharide with six carbon atoms and an aldehyde functional group is called a(n) ________.

A) hexose

B) ketohexose

C) aldohexose

D) ketoheptose

E) ketose

Diff: 1

Learning Objective: 24.2 Describe how monosaccharides are classified

6) A monosaccharide with five carbon atoms and a ketone functional group is called a(n) ________.

A) aldose

B) ketohexose

C) aldopentose

D) ketopentose

E) pentose

Diff: 1

Learning Objective: 24.2 Describe how monosaccharides are classified

7) Which of the choices is a ketohexose?

A) D-lyxose

B) D-fructose

C) D-ribose

D) D-glucose

E) D-xylulose

Diff: 1

Learning Objective: 24.2 Describe how monosaccharides are classified

8) Which of the choices is an aldohexose?

A) D-lyxose

B) D-fructose

C) D-ribose

D) D-glucose

E) D-xylulose

Diff: 1

Learning Objective: 24.2 Describe how monosaccharides are classified

9) Which of the choices is a ketopentose?

A) D-lyxose

B) D-fructose

C) D-ribose

D) D-glucose

E) D-xylulose

Diff: 1

Learning Objective: 24.2 Describe how monosaccharides are classified

10) Which of the choices is an aldopentose?

A) D-galactose

B) D-fructose

C) D-ribose

D) D-glucose

E) D-xylulose

Diff: 1

Learning Objective: 24.2 Describe how monosaccharides are classified

11) Which of the choices best describes L-galactose?

A) aldopentose

B) aldohexose

C) ketopentose

D) ketohexose

E) aldotetrose

Diff: 2

Learning Objective: 24.2 Describe how monosaccharides are classified

12) Which of the choices best describes the relationship between D-glucose and D-fructose?

A) enantiomers

B) epimers

C) anomers

D) constitutional isomers

E) diastereomers

Diff: 1

Learning Objective: 24.2 Describe how monosaccharides are classified

13) Which of the choices is an L-aldohexose?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 24.2 Describe how monosaccharides are classified

14) Which of the choices is a D-aldopentose?

A) I

B) II

C) III

D) IV

E) I and V

Diff: 1

Learning Objective: 24.2 Describe how monosaccharides are classified

15) Which of the choices is a L-ketopentose?

A) I

B) II

C) III

D) IV

E) III and IV

Diff: 1

Learning Objective: 24.2 Describe how monosaccharides are classified

16) Identify the compound that is found in nature.

A) D-(+)-glyceraldehyde

B) L-(+)-glyceraldehyde

C) D-(-)-glyceraldehyde

D) L-(-)-glyceraldehyde

E) none of these

Diff: 1

Learning Objective: 24.2 Describe how monosaccharides are classified

17) Degradation of naturally occurring glucose produces ________ that is ________.

A) D-glyceraldehyde; dextrorotatory

B) D-glyceraldehyde; levorotatory

C) L-glyceraldehyde; dextrorotatory

D) L-glyceraldehyde; levorotatory

E) none of these

Diff: 1

Learning Objective: 24.2 Describe how monosaccharides are classified

18) Degradation of synthetic glucose produces ________ that is ________.

A) glyceraldehyde; dextrorotatory

B) glyceraldehyde; levorotatory

C) glyceraldehyde; both dextrorotatory and levorotatory

D) none of these

Diff: 1

Learning Objective: 24.2 Describe how monosaccharides are classified

19) Which of the choices give the characteristics of a D-sugar?

A) R configuration and dextrorotatory

B) R configuration and levorotatory

C) S configuration and dextrorotatory

D) S configuration and levorotatory

E) D and L have no correlation to configuration and rotation of plane-polarized light.

Diff: 1

Learning Objective: 24.2 Describe how monosaccharides are classified

20) All natural occurring sugars are ________.

A) D sugars

B) L sugars

C) a combination of D and L sugars

D) neither D nor L sugars

Diff: 1

Learning Objective: 24.2 Describe how monosaccharides are classified

21) Which of the given aldohexoses is dextrorotatory?

A) D-glucose

B) D-galactose

C) D-gulose

D) D-mannose

E) cannot predict

Diff: 2

Learning Objective: 24.2 Describe how monosaccharides are classified

22) In the Fischer projection of D-glyceraldehyde, the OH group connected to the chirality center farthest from the carbonyl group is pointing ________.

A) to the left

B) to the right

C) up

D) down

E) all of these

Diff: 2

Learning Objective: 24.2 Describe how monosaccharides are classified

23) Which of the given compounds represent a pair of enantiomers?

A) I and III

B) II and IV

C) III and V

D) IV

E) none of these

Diff: 2

Learning Objective: 24.3 Using the mnemonic device, provide names for all eight D-aldohexoses

24) Which choices gives the classification for D-erythrose?

A) aldotetrose

B) ketotetrose

C) aldopentose

D) ketopentose

E) aldohexose

F) ketohexose

Diff: 1

Learning Objective: 24.3 Using the mnemonic device, provide names for all eight D-aldohexoses

25) Which choice gives the classification for D-threose?

A) aldotetrose

B) ketotetrose

C) aldopentose

D) ketopentose

E) aldohexose

F) ketohexose

Diff: 1

Learning Objective: 24.3 Using the mnemonic device, provide names for all eight D-aldohexoses

26) Which choice gives the classification for D-ribose?

A) aldotetrose

B) ketotetrose

C) aldopentose

D) ketopentose

E) aldohexose

F) ketohexose

Diff: 1

Learning Objective: 24.3 Using the mnemonic device, provide names for all eight D-aldohexoses

27) Which choice gives the classification for D-galactose?

A) aldotetrose

B) ketotetrose

C) aldopentose

D) ketopentose

E) aldohexose

F) ketohexose

Diff: 1

Learning Objective: 24.3 Using the mnemonic device, provide names for all eight D-aldohexoses

28) Of the possible stereoisomers for galactose, how many are L-isomers?

A) 8

B) 6

C) 10

D) 3

E) 4

Diff: 1

Learning Objective: 24.3 Using the mnemonic device, provide names for all eight D-aldohexoses

29) Of the possible stereoisomers for glucose, how many are D-isomers?

A) 8

B) 6

C) 10

D) 3

E) 4

Diff: 1

Learning Objective: 24.3 Using the mnemonic device, provide names for all eight D-aldohexoses

30) How many stereoisomers are possible for an aldohexose?

A) 8

B) 16

C) 10

D) 12

E) 4

Diff: 1

Learning Objective: 24.3 Using the mnemonic device, provide names for all eight D-aldohexoses

31) Which choice shows the Fisher projection for L-glucose?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.3 Using the mnemonic device, provide names for all eight D-aldohexoses

32) Which choice shows the Fisher projection for D-galactose?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.3 Using the mnemonic device, provide names for all eight D-aldohexoses

33) Which one of the choices is the correct Fischer projection for D-gulose?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.3 Using the mnemonic device, provide names for all eight D-aldohexoses

34) Which of the choices is a L-hexose?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.3 Using the mnemonic device, provide names for all eight D-aldohexoses

35) Which of the choices is the correct stereochemical configuration for D-xylose?

A) 2S,3R,4S

B) 2R,3S,4R

C) 2R,3R,4S

D) 2S,3S,4R

E) 2S,3S,4S

Diff: 2

Learning Objective: 24.3 Using the mnemonic device, provide names for all eight D-aldohexoses

36) Which of the choices is the correct stereochemical configuration for D-mannose?

A) 2S,3S,4R,5R

B) 2R,3S,4R,5S

C) 2R,3R,4S,5S

D) 2S,3S,4R,5S

E) 2S,3R,4S,5R

Diff: 2

Learning Objective: 24.3 Using the mnemonic device, provide names for all eight D-aldohexoses

37) What is the most common aldohexose?

A) D-allose

B) D-mannose

C) D-galactose

D) D-glucose

E) D-altrose

Diff: 1

Learning Objective: 24.3 Using the mnemonic device, provide names for all eight D-aldohexoses

38) Draw a Fisher projection for the enantiomer of D-glucose.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.3 Using the mnemonic device, provide names for all eight D-aldohexoses

39) How many stereoisomers are possible for fructose?

A) 8

B) 6

C) 10

D) 3

E) 4

Diff: 2

Learning Objective: 24.4 Provide names for the most common D-ketoses

40) Of the possible stereoisomers for fructose, how many are D-isomers?

A) 8

B) 6

C) 10

D) 2

E) 4

Diff: 2

Learning Objective: 24.4 Provide names for the most common D-ketoses

41) Draw a Fisher projection for D-fructose.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.4 Provide names for the most common D-ketoses

42) Which of the choices is the correct structure for L-fructose?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.4 Provide names for the most common D-ketoses

43) What is the most common naturally occurring ketose?

A) D-xyulose

B) D-fructose

C) L-fructose

D) L-xyulose

E) D-ribulose

Diff: 1

Learning Objective: 24.4 Provide names for the most common D-ketoses

44) Which of the choices best describes the relationship between α-D-glucopyranose and β-D-glucopyranose?

A) enantiomers

B) anomers

C) diastereomers

D) constitutional isomers

E) none of these

Diff: 1

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

45) What is the predicted major product of the reaction shown?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

46) What is the predicted major product of the reaction shown?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

47) What is the reactant for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

48) Anomers of D-glucopyranose differ in stereochemistry at ________ carbon.

A) C1

B) C2

C) C3

D) C4

E) C5

Diff: 1

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

49) Which carbon in the given monosaccharide is the anomeric carbon?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

50) Six-membered cyclic hemiacetal carbohydrates are called ________.

A) furanose

B) pyranose

C) ketopentose

D) aldopentose

E) none of these

Diff: 1

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

51) Five-membered cyclic hemiacetal carbohydrates are called ________.

A) furanose

B) pyranose

C) ketohexose

D) aldohexose

E) none of these

Diff: 2

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

52) What is the correct Haworth projection for α-D-glucopyranose?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

53) What is the correct Haworth projection for β-D-allopyranose?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

54) What is the correct name for the compound shown?

A) α-D-glucopyranose

B) α-D-allopyranose

C) β-D-glucopyranose

D) α-D-galactopyranose

E) β-D-gulopyranose

Diff: 2

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

55) What is the correct name for the compound shown?

A) α-D-idopyranose

B) β-D-altopyranose

C) β-D-glucopyranose

D) α-D-galactopyranose

E) β-D-gulopyranose

Diff: 2

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

56) Pyranose forms of monosaccharides are ________.

A) 5-membered cyclic hemiacetals

B) 6-membered cyclic acetals

C) 5-membered cyclic acetals

D) 6-membered cyclic hemiacetals

E) none of these

Diff: 1

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

57) Furanose forms of monosaccharides are ________.

A) 5-membered cyclic hemiacetals

B) 6-membered cyclic acetals

C) 5-membered cyclic acetals

D) 6-membered cyclic hemiacetals

E) none of these

Diff: 1

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

58) Which of the compound(s) shown would undergo mutarotation in aqueous solution?

A) I

B) II and III

C) III and IV

D) I, II, and III

E) all of these

Diff: 2

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

59) Which of the compound(s) shown would not undergo mutarotation in aqueous solution?

A) I

B) II and IV

C) III

D) IV

E) II, III and IV

Diff: 2

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

60) What is the correct name for the compound shown?

A) α-D-fructofuranose

B) β-D-sorbofuranose

C) α-D-glucopyranose

D) β-D- fructofuranose

E) β-D-gulopyranose

Diff: 2

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

61) Draw the Haworth projection for β-D-erythrofuranose.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

62) Which of the given structures represents β-D-glucopyranose?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

63) Draw the chair conformation of α-D-galactopyranose.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

64) Draw the Fischer projection for the open-chain form of the given cyclic monosaccharide.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

65) Draw the alpha chair conformation for the monosaccharide shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

66) Anomers of D-fructofuranose differ in stereochemistry at ________ carbon.

A) C1

B) C2

C) C3

D) C4

E) C5

Diff: 1

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

67) What reagents are necessary to carry out the conversion shown?

A) excess CH3I/Ag2O

B)

C)

D)

E)

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

68) What is(are) the predicted product(s) when β-D-galactopyranose reacts with excess acetic anhydride in the presence of pyridine?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

69) What reagents are needed to carry out the conversion shown?

A) excess CH3I/Ag2O

B) excess CH2CH2I/Ag2O

C) excess CH3I/pyridine

D) excess CH3CH2I/pyridine

E) excess CH3CH2I/Ag2O/pyridine

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

70) All of the —OH groups on a monosaccharides can be converted to ethers via the Williamson ether synthesis with CH3I in the presence of ________.

A) strong base

B) weak base

C) strong acid

D) weak acid

Diff: 1

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

71) Which of the compound(s) shown is a glycoside?

A) I

B) II

C) II and III

D) III and IV

E) II, III and IV

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

72) What reagents are needed to carry out the conversion shown?

A) CH3I/Ag2O

B) CH3OH/Ag2O

C) CH3OH/pyridine

D) CH3CH2OH/HCl

E) CH3OH/HCl

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

73) What are the predicted products of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

74) A glycoside is formed from D-glucopyranose by alkylating the —OH attached to ________.

A) C-1

B) C-2

C) C-3

D) C-4

E) C-5

Diff: 1

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

75) What is(are) the predicted product(s) of the reaction shown?

A) I

B) I and II

C) III and IV

D) IV

E) I, II and IV

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

76) Epimers are diastereomers that differ from each other in the configuration of ________ chiral center(s).

A) no

B) one

C) two

D) two or three

E) three or four

Diff: 1

Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

77) Which of the compounds shown is(are) an epimer(s) of D-glucose?

A) I

B) II

C) I and III

D) II and IV

E) I and II

Diff: 1

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

78) Which of the choices best describes the relationship between D-glucose and D-galactose?

A) enantiomers

B) anomers

C) epimers

D) constitutional isomers

E) none of these

Diff: 1

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

79) D-glucose and D-galactose are ________ epimers of each other.

A) C-1

B) C-2

C) C-3

D) C-4

E) C-5

Diff: 1

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

80) D-ribulose and D-xylulose are ________ epimers of each other.

A) C-1

B) C-2

C) C-3

D) C-4

E) C-5

Diff: 1

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

81) When D-glucose is treated with aqueous NaOH, it undergoes ________.

A) mutarotation

B) oxidation

C) glycoside formation

D) epimerization

E) none of these

Diff: 1

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

82) What is(are) the predicted product(s) of the reaction shown?

A) I

B) II

C) III

D) IV

E) II and IV

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

83) What is(are) the predicted product(s) of the reaction shown?

A) I

B) II

C) I and III

D) IV

E) I and V

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

84) Which of the given D-aldoses will produce an optically inactive product when treated with NaBH4/H2O?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

85) When D-threose is treated with NaBH4/H2O, it forms ________.

A) a racemic mixture of alditols

B) a meso alditol

C) an optically active alditol

D) an optically active aldonic acid

E) none of these

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

86) When D-erythrose is treated with NaBH4/H2O, it forms ________.

A) a racemic mixture of alditols

B) a meso alditol

C) an optically active alditol

D) an optically active aldonic acid

E) none of these

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

87) Which of the compound(s) shown would give a positive Tollens test?

A) I

B) II

C) III

D) IV

E) I and II

Diff: 1

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

88) Which one of the compounds shown is a non-reducing sugar?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

89) Which one of the compounds shown would give a positive test with Benedict's solution?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

90) What is(are) the predicted product(s) of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

91) What is(are) the predicted product(s) of the reaction shown?

A) I

B) II

C) III

D) IV

E) D-fructose is not oxidized by bromine water.

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

92) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

93) What is(are) the predicted product(s) of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

94) When D-ribose is treated with nitric acid, it forms ________.

A) a racemic mixture of aldonic acids

B) a meso aldaric acid

C) an optically active aldaric acid

D) an optically active aldonic acid

E) a meso aldonic acid

Diff: 1

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

95) Which of the compounds shown would produce an optically active aldaric acid?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

96) What is(are) the predicted product(s) of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

97) What reagents are needed to carry out the conversion shown?

A) Br2/H2O

B) NaOH/H2O

C) HNO3

D) Ag+/NH3/H2O

E) A and D

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

98) The sequence of reactions that results in a chain lengthening of the aldose chain is called the ________ synthesis.

A) Williamson

B) Wohl

C) Kiliani-Fischer

D) Fischer

E) Friedl-Crafts

Diff: 1

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

99) Which of the compounds shown would produce D-glucose and D-mannose when treated with HCN followed by H2/Pd/BaSO4/H2O?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

100) What are the predicted products of the Kiliani-Fischer synthesis shown?

A) I and V

B) II and IV

C) I and III

D) III and IV

E) II and V

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

101) Which aldose would produce D-ribose and D-arabinose when subjected to the Kiliani-Fischer synthesis?

A) D-threose

B) D-xylose

C) D-erythrose

D) D-allose

E) D-lyxose

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

102) What are the predicted products of the Kiliani-Fischer synthesis shown?

A) D-ribose and D-arabinose

B) D-glucose and D-galactose

C) D-altrose and D-mannose

D) D-galactose and D-talose

E) D-gulose and D-iodose

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

103) What are the reagents needed to carry out the Kiliani-Fischer synthesis shown?

A) 1. HCN

2. H2/Pd/BaSO4/H2O

B) 1. NaBH4/H2O

2. CH3OH/HCl

C) excess CH3I/Ag2O

D) 1. NH2OH

2. acetic anhydride

3. NaOCH3

E) 1. Br2/H2O

2. NaBH4/H2O

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

104) Which of the compounds shown would produce D-glucose and D-mannose when subjected to Kiliani-Fischer synthesis?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

105) The sequence of reactions that results in a chain shortening of the aldose chain is called the ________ degradation.

A) Williamson

B) Wohl

C) Kiliani-Fischer

D) Fischer

E) Friedl-Crafts

Diff: 1

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

106) What is the predicted products of the Wohl degradation shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

107) What is the predicted product for the Wohl degradation shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

108) What is(are) the predicted product(s) of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

109) Which of the given pairs of D-aldohexoses would both produce the same product when subjected to Wohl degradation?

A) D-glucose and D-galactose

B) D-mannose and D-galactose

C) D-glucose and D-gulose

D) D-allose and D-altrose

E) D-glucose and D-allose

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

110) D-mannose when subjected to Wohl degradation followed by Br2/H2O produces the same aldonic acid as does ________ when treated with Br2/H2O.

A) D-arabinose

B) D-ribose

C) D-xylose

D) D-lyxose

E) D-threose

Diff: 2

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

111) An optically active D-aldohexose was treated with NaBH4/H2O and produced an optically inactive alditol. When the same D-aldohexose was subjected to Wohl degradation followed by HNO3 it produced an optically inactive aldaric acid. What is the structure of this D-aldohexose?

A) D-glucose

B) D-mannose

C) D-allose

D) D-idose

E) D-talose

Diff: 3

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

112) When an optically active D-aldopentose was subjected to Kiliani-Fischer synthesis, followed by NaBH4/H2O, it produced a mixture of an optically active and an optically inactive alditol. When the same D-aldopentose was subjected to Wohl degradation followed by HNO3 it produced an optically inactive aldaric acid. Provide the structure of this D-aldopentose.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides

113) Which one of the choices is a correct structure for α-maltose?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides

114) Which one of the choices is a correct structure for β-lactose?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides

115) Which one of the choices is a correct structure for sucrose?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides

116) Which one of the choices is a correct structure for β-cellobiose?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides

117) Which of the disaccharides shown is a reducing sugar?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides

118) Which of the given statements best describe the main difference between maltose and cellobiose?

A) Maltose has a β-1-4 glycosidic linkage and cellobiose has an α-1-4 glycosidic linkage.

B) Maltose is comprised of β-D-glucopyranose and cellobiose is comprised of α-D-glucopyranose.

C) Maltose is comprised of α-D-glucopyranose and cellobiose is comprised of β-D-glucopyranose.

D) Maltose has an α-1-4 glycosidic linkage and cellobiose has a β-1-4 glycosidic linkage.

E) C and D

Diff: 2

Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides

119) Which of the choices is a reducing sugar with a 1→4 α-glycosidic linkage?

A) maltose

B) cellobiose

C) sucrose

D) lactose

E) B and D

Diff: 1

Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides

120) What is(are) the predicted product(s) when lactose is treated with Br2/H2O?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides

121) What is(are) the predicted product(s) when maltose is treated with NaBH4/H2O?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides

122) What is(are) the predicted product(s) when maltose is treated with CH3OH/HCl?

A) I

B) II

C) III

D) A and B

E) C and D

Diff: 2

Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides

123) What is(are) the predicted product(s) when cellobiose is treated with excess acetic anhydride/pyridine?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides

124) What are the monosaccharide(s) in α-maltose?

A) two β-D-glucopyranose

B) β-D-galactopyranose and β-D-glucopyranose

C) α-D-glucopyranose and β-D-fructofuranose

D) two α-D-glucopyranose

E) two β-D-fructofuranose

Diff: 1

Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides

125) What are the monosaccharide(s) in β-cellobiose?

A) two β-D-glucopyranose

B) β-D-galactopyranose and β-D-glucopyranose

C) α-D-glucopyranose and β-D-fructofuranose

D) two α-D-glucopyranose

E) two β-D-fructofuranose

Diff: 1

Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides

126) What are the monosaccharide(s) in β-lactose?

A) two β-D-glucopyranose

B) β-D-galactopyranose and β-D-glucopyranose

C) α-D-glucopyranose and β-D-fructofuranose

D) two α-D-glucopyranose

E) two β-D-fructofuranose

Diff: 1

Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides

127) Identify the monosaccharide(s) in sucrose.

A) two β-D-glucopyranose

B) β-D-galactopyranose and β-D-glucopyranose

C) α-D-glucopyranose and β-D-fructofuranose

D) two α-D-glucopyranose

E) two β-D-fructofuranose

Diff: 1

Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides

128) Which of the given disaccharides is(are) α-glucoside(s)?

A) sucrose

B) maltose

C) lactose

D) cellobiose

E) both A and B

Diff: 1

Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides

129) Which of the given disaccharides is(are) β-galactoside(s)?

A) sucrose

B) maltose

C) lactose

D) cellobiose

E) both A and B

Diff: 1

Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides

130) Which of the given disaccharides is (are) not a reducing sugar(s)?

A) sucrose

B) maltose

C) lactose

D) cellobiose

E) none of these

Diff: 2

Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides

131) What is the monomer in starch?

A) α-D-glucose

B) β-D-glucose

C) α-D-galactose

D) β-D-fructose

E) maltose

Diff: 2

Learning Objective: 24.8 Describe the structure of a polysaccharide, and give three examples of polysaccharides

132) What is the monomer in cellulose?

A) α-D-glucose

B) β-D-glucose

C) α-D-galactose

D) β-D-fructose

E) maltose

Diff: 1

Learning Objective: 24.8 Describe the structure of a polysaccharide, and give three examples of polysaccharides

133) What is the monomer in glycogen?

A) α-D-glucose

B) β-D-glucose

C) α-D-galactose

D) β-D-fructose

E) maltose

Diff: 1

Learning Objective: 24.8 Describe the structure of a polysaccharide, and give three examples of polysaccharides

134) Raffinose is a trisaccharide found in whole grains. What is the correct description of the glycosidic linkage(s) in raffinose?

A) 1→6 α at galactose and glucose and 1→2 α at glucose and fructose

B) 1→4 α at galactose and glucose and 1→2 α at glucose and fructose

C) 1→6 α at galactose and glucose and 1→6 α at glucose and fructose

D) 1→6 β at galactose and glucose and 1→2 β at glucose and fructose

E) 1→4 β at galactose and glucose and 1→2 β at glucose and fructose

Diff: 2

Learning Objective: 24.8 Describe the structure of a polysaccharide, and give three examples of polysaccharides

135) Raffinose is a trisaccharide found in whole grains. Is raffinose a reducing sugar?

A) yes

B) no

Diff: 2

Learning Objective: 24.8 Describe the structure of a polysaccharide, and give three examples of polysaccharides

136) A polysaccharide that is a major component in the exoskeletons of insects and arthropods is called ________.

A) cellulose

B) chitin

C) glycogen

D) glycoasminoglycans

E) peptidoglycan

Diff: 2

Learning Objective: 24.9 Describe the structure of an amino sugar

137) The main difference between cellulose and chitin is that ________.

A) cellulose has β-glycosidic linkages; chitin has α-glycosidic linkages

B) cellulose has α-glycosidic linkages; chitin has β-glycosidic linkages

C) cellulose is composed of D-glucose units; chitin is composed of an N-acetyl derivative of glucose, glucosamine

D) cellulose has a linear structure; chitin has a helical structure

E) cellulose has 1,6 branching; chitin has no branching

Diff: 2

Learning Objective: 24.9 Describe the structure of an amino sugar

138) Which one of the given heterocyclic amines is not a base in DNA?

A) uracil

B) thymine

C) cytosine

D) adenine

E) guanine

Diff: 1

Learning Objective: 24.10 Explain how N-glycosides are formed, and discuss the relationship of N-glycosides to DNA and RNA

139) Which one of the given heterocyclic amines is not a base in RNA?

A) uracil

B) thymine

C) cytosine

D) adenine

E) guanine

Diff: 1

Learning Objective: 24.10 Explain how N-glycosides are formed, and discuss the relationship of N-glycosides to DNA and RNA

140) What is the difference between a nucleoside and a nucleotide?

A) A nucleotide is a phosphorylated nucleoside.

B) A nucleoside is a phosphorylated nucleotide.

C) A nucleotide is a deoxynucleoside.

D) A nucleoside is a deoxynucleotide.

E) none of these

Diff: 1

Learning Objective: 24.10 Explain how N-glycosides are formed, and discuss the relationship of N-glycosides to DNA and RNA

141) What is(are) the predicted product(s) when α-D-glucose is treated with methanamine in the presence of acid?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.10 Explain how N-glycosides are formed, and discuss the relationship of N-glycosides to DNA and RNA

142) Provide the structure for cytidine.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.10 Explain how N-glycosides are formed, and discuss the relationship of N-glycosides to DNA and RNA

143) Provide the structure for uridine.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 24.10 Explain how N-glycosides are formed, and discuss the relationship of N-glycosides to DNA and RNA

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