Exam 28: Carbohydrates

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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?

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B

Upon hydrolysis of amylopectin, what sugar is formed?

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D

Cellulose is a polysaccharide with ________________________ linkages.

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A

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?

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What is the classification of pyranose forms of monosaccharides?

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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?

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

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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?

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Upon hydrolysis of amylose, what sugar is formed?

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What is the composition of maltose?

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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.

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How many possible stereoisomers are there of the following heptose? How many possible stereoisomers are there of the following heptose?

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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?

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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.

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Which of the following compounds is a anomer? Which of the following compounds is a <font face=symbol></font> anomer?

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What are the products of the following reaction? What are the products of the following reaction?

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

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What is the composition of lactose?

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Amylose is a polysaccharide with ________________________ linkages.

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Which sugar is represented by the line angle structure below? Which sugar is represented by the line angle structure below?

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