(a) Interpretation: Whether the configuration of the aldose, 6-deoxyglucose is D or L is to be stated. Concept introduction: Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

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Answer 1

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Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 24, Problem 24.4P

Interpretation Introduction

(a)

Interpretation:

Whether the configuration of the aldose, 6-deoxyglucose is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

Interpretation Introduction

(b)

Interpretation:

Whether the configuration of glucose enantiomer with R configuration at carbon -3 is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

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(a) Which of the d-aldopentoses will give optically active aldaric acids on oxidation with HNO3 ?(b) Which of the d-aldotetroses will give optically active aldaric acids on oxidation with HNO3 ?(c) Sugar X is known to be a d-aldohexose. On oxidation with HNO3, X gives an optically inactive aldaric acid. WhenX is degraded to an aldopentose, oxidation of the aldopentose gives an optically active aldaric acid. Determine thestructure of X.(d) Even though sugar X gives an optically inactive aldaric acid, the pentose formed by degradation gives an opticallyactive aldaric acid. Does this finding contradict the principle that optically inactive reagents cannot form opticallyactive products?(e) Show what product results if the aldopentose formed from degradation of X is further degraded to an aldotetrose.Does HNO3 oxidize this aldotetrose to an optically active aldaric acid?

(a) Label all the O atoms that are part of a glycoside in rebaudioside A. Rebaudioside A, marketed under the trade name Truvia, is a sweet glycoside obtained from the stevia plant, which has been used for centuries in Paraguay to sweeten foods. (b) The alcohol or phenol formed from the hydrolysis of a glycoside is called an aglycon. What aglycon and monosaccharides are formed by the hydrolysis of rebaudioside A?

Draw the following monosaccharides, using chair conformations for the pyranoses andHaworth projections for the furanoses.(a) a-d-mannopyranose (C2 epimer of glucose)(b) b-d-galactopyranose (C4 epimer of glucose)(c) b-d-allopyranose (C3 epimer of glucose)(d) a-d-arabinofuranose(e) b-d-ribofuranose (C2 epimer of arabinose)

Answer 2

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Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 24, Problem 24.4P

Interpretation Introduction

(a)

Interpretation:

Whether the configuration of the aldose, 6-deoxyglucose is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

Interpretation Introduction

(b)

Interpretation:

Whether the configuration of glucose enantiomer with R configuration at carbon -3 is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

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Answer 3

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Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 24, Problem 24.4P

Interpretation Introduction

(a)

Interpretation:

Whether the configuration of the aldose, 6-deoxyglucose is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

Interpretation Introduction

(b)

Interpretation:

Whether the configuration of glucose enantiomer with R configuration at carbon -3 is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

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Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 24, Problem 24.4P

Interpretation Introduction

(a)

Interpretation:

Whether the configuration of the aldose, 6-deoxyglucose is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

Interpretation Introduction

(b)

Interpretation:

Whether the configuration of glucose enantiomer with R configuration at carbon -3 is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

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Answer 5

Chapter 24, Problem 24.4P

Interpretation Introduction

(a)

Interpretation:

Whether the configuration of the aldose, 6-deoxyglucose is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

Interpretation Introduction

(b)

Interpretation:

Whether the configuration of glucose enantiomer with R configuration at carbon -3 is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

Answer 6

Chapter 24, Problem 24.4P

Interpretation Introduction

(a)

Interpretation:

Whether the configuration of the aldose, 6-deoxyglucose is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

Answer 7

Chapter 24, Problem 24.4P

Interpretation Introduction

(a)

Interpretation:

Whether the configuration of the aldose, 6-deoxyglucose is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

Answer 8

Interpretation Introduction

(b)

Interpretation:

Whether the configuration of glucose enantiomer with R configuration at carbon -3 is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

Answer 9

Interpretation Introduction

(b)

Interpretation:

Whether the configuration of glucose enantiomer with R configuration at carbon -3 is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

Answer 10

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Answer 12

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Answer 13

Ch. 24 - Prob. 24.1P Ch. 24 - Prob. 24.2P Ch. 24 - Prob. 24.3P Ch. 24 - Prob. 24.4P Ch. 24 - Prob. 24.5P Ch. 24 - Prob. 24.6P Ch. 24 - Prob. 24.7P Ch. 24 - Prob. 24.8P Ch. 24 - Prob. 24.9P Ch. 24 - Prob. 24.10P

Solution Summary: The author explains the structure of the aldose, 6-deoxyglucose, and the stereoisomers of glyceraldehydes.

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Chapter 24 Solutions