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After a series of Kiliani-Fischer syntheses on D-glyceraldehyde, an unknown sugar was isolated from the reaction mixture. The following experimental data was obtained. What is the structure of this unknown sugar? Data: - Molecular formula: C6H12O6 - Reacts with phenylhydrazine to give an osazone, mp 178°C. - Reacts with HNO3 to give an optically active aldaric acid. - Wohl degradation followed by HNO3 oxidation gives an optically inactive Aldaric acid. - Two Wohl degradations followed by HNO3 oxidation give a meso-tartaric acid. After a series of Kiliani-Fischer syntheses on D-glyceraldehyde, an unknown sugar was isolated from the reaction mixture. The following experimental data was obtained. What is the structure of this unknown sugar? Data: - Molecular formula: C<sub>6</sub>H<sub>12</sub>O<sub>6</sub> - Reacts with phenylhydrazine to give an osazone, mp 178°C. - Reacts with HNO<sub>3</sub> to give an optically active aldaric acid. - Wohl degradation followed by HNO<sub>3</sub> oxidation gives an optically inactive Aldaric acid. - Two Wohl degradations followed by HNO<sub>3</sub> oxidation give a meso-tartaric acid. A) A B) B C) C D) D


A) A
B) B
C) C
D) D

E) None of the above
F) All of the above

Correct Answer

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Which is the correct Haworth projection for the anomer of D-glucose? Which is the correct Haworth projection for the <font face= symbol ></font> anomer of D-glucose? A) A B) B C) C D) D


A) A
B) B
C) C
D) D

E) A) and B)
F) A) and C)

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What is the composition of lactose?


A) two glucose units with a -1,4'-glycoside bond
B) one glucose and one fructose unit with a -glycosidic bond to the 2'carbon of a fructofuranose ring
C) one galactose and one glucose unit with a -1,4'-glycoside bond
D) repeating unit of glucose units joined in a -1,4'-glycosidic linkage

E) A) and D)
F) B) and C)

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What is the composition of maltose?


A) two glucose units with a -1,4'-glycoside bond
B) one glucose and one fructose unit with a -glycosidic bond to the 2'carbon of a fructofuranose ring
C) one galactose and one glucose unit with a -1,4'-glycoside bond
D) repeating unit of glucose units joined in a -1,4'-glycosidic linkage

E) A) and D)
F) B) and C)

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How many possible stereoisomers are there of the following heptose? How many possible stereoisomers are there of the following heptose? A) 16 B) 21 C) 32 D) 64


A) 16
B) 21
C) 32
D) 64

E) B) and C)
F) B) and D)

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Is the following carbohydrate D or L? Provide an explanation for your answer. Is the following carbohydrate D or L? Provide an explanation for your answer. A) It is D because the OH group on C2 is on the right. B) It is L because the OH group on C4 is on the left. C) It is L because the OH group on C3 is on the left. D) It is D because the sugar is not symmetric.


A) It is D because the OH group on C2 is on the right.
B) It is L because the OH group on C4 is on the left.
C) It is L because the OH group on C3 is on the left.
D) It is D because the sugar is not symmetric.

E) All of the above
F) B) and C)

Correct Answer

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Which of the following sugars can be classified as a ketohexose? Which of the following sugars can be classified as a ketohexose? A) A B) B C) C D) D


A) A
B) B
C) C
D) D

E) None of the above
F) C) and D)

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What are the products of the following reaction? What are the products of the following reaction? A) A B) B C) C D) D


A) A
B) B
C) C
D) D

E) All of the above
F) A) and B)

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Which sugar is represented by the line angle structure below? Which sugar is represented by the line angle structure below? A) D-fructose B) D-sorbose C) L-psicose D) L-tagatose


A) D-fructose
B) D-sorbose
C) L-psicose
D) L-tagatose

E) B) and D)
F) None of the above

Correct Answer

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What is the correct chair form for the anomer of D-mannose? What is the correct chair form for the <font face= symbol ></font> anomer of D-mannose? A) A B) B C) C D) D


A) A
B) B
C) C
D) D

E) B) and C)
F) All of the above

Correct Answer

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Which of the following pairs of carbohydrates will afford the same product from a Wohl degradation?


A) xylose/glucose
B) ribose/arabinose
C) fructose/mannose
D) lyxose/threose

E) A) and C)
F) A) and B)

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The following reaction is an example of a base-catalyzed epimerization reaction in which a ketose is converted to a pair of aldoses. What are the products from this reaction? The following reaction is an example of a base-catalyzed epimerization reaction in which a ketose is converted to a pair of aldoses. What are the products from this reaction? A) D-glucose and D-mannose B) D-galactose and D-talose C) D-talose and D-idose D) D-glucose and D-idose


A) D-glucose and D-mannose
B) D-galactose and D-talose
C) D-talose and D-idose
D) D-glucose and D-idose

E) A) and C)
F) A) and B)

Correct Answer

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Amylose is a polysaccharide with ________________________ linkages.


A) "-1,4'-glycosidic"
B) "-1,4'-glycosidic"
C) "-1,6'-glycosidic"
D) "-1,6'-glycosidic"

E) A) and B)
F) All of the above

Correct Answer

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What is the classification of pyranose forms of monosaccharides?


A) 5-membered cyclic hemiacetals
B) 6-membered cyclic acetals
C) 5-membered cyclic acetals
D) 6-membered cyclic hemiacetals

E) All of the above
F) A) and B)

Correct Answer

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Upon hydrolysis of amylose, what sugar is formed?


A) sucrose
B) maltose
C) lactose
D) glucose

E) A) and D)
F) B) and C)

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Cellulose is a polysaccharide with ________________________ linkages.


A) "-1,4'-glycosidic"
B) "-1,4'-glycosidic"
C) "-1,6'-glycosidic"
D) "-1,6'-glycosidic"

E) A) and B)
F) A) and C)

Correct Answer

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A

Does a monosaccharide prefer to exist in the open-chain or closed-ring form?


A) open
B) closed
C) Both forms exist in equal ratios.

D) A) and C)
E) All of the above

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Which of the following compounds is a anomer? Which of the following compounds is a <font face= symbol ></font> anomer? A) A B) B C) C D) D


A) A
B) B
C) C
D) D

E) None of the above
F) B) and C)

Correct Answer

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Oxidation of a D-hexose with nitric acid forms an optically active aldaric acid. A Wohl degradation of the same D-hexose followed by oxidation with nitric acid forms an optically active aldaric acid. What are the three possible D-hexoses that fit this data?


A) D-allose, D-altrose and D-glucose
B) D-glucose, D- mannose and D-talose
C) D-glucose, D-idose and D-altrose
D) D-galactose, D-talose and D-mannose

E) A) and B)
F) A) and C)

Correct Answer

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B

Upon hydrolysis of amylopectin, what sugar is formed?


A) sucrose
B) maltose
C) lactose
D) glucose

E) A) and B)
F) A) and C)

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D

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