(a) Interpretation: The conversion of D-glucose into the given compound is to be predicted. Concept introduction: The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide . Glycosidic linkages are hydrolyzed in presence of acid to form cyclic hemiacetal and corresponding alcohol.

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Answer 1

Question

Chapter 28, Problem 28.55P

Interpretation Introduction

(a)

Interpretation: The conversion of D-glucose into the given compound is to be predicted.

Concept introduction: The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide. Glycosidic linkages are hydrolyzed in presence of acid to form cyclic hemiacetal and corresponding alcohol.

Interpretation Introduction

(b)

Interpretation: The conversion of D-glucose into the given compound is to be predicted.

Concept introduction: The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide. The carbonyl group of aldoses can be reduced to alcohol using metal hydrides.

Interpretation Introduction

(c)

Interpretation: The conversion of D-glucose into the given compound is to be predicted.

Concept introduction: The aldehyde group of aldoses oxidizes to carboxylic acid group in presence of bromine water to form aldonic acids. The hydroxyl groups of monosaccharides are converted into the ester groups in presence of base and acetic anhydride or acetyl chloride.

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How would you convert D-glucose to each compound? More than onestep is required.

a.Label the four stereogenic centers in sorbitol as R or S. b.How are sorbitol and A related? c. How are sorbitol and B related?

Which one is b-D glucose and which one is a-L glucose ? 2. Which one is b-fructose and which a-L fructose?

Answer 2

Question

Chapter 28, Problem 28.55P

Interpretation Introduction

(a)

Interpretation: The conversion of D-glucose into the given compound is to be predicted.

Concept introduction: The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide. Glycosidic linkages are hydrolyzed in presence of acid to form cyclic hemiacetal and corresponding alcohol.

Interpretation Introduction

(b)

Interpretation: The conversion of D-glucose into the given compound is to be predicted.

Concept introduction: The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide. The carbonyl group of aldoses can be reduced to alcohol using metal hydrides.

Interpretation Introduction

(c)

Interpretation: The conversion of D-glucose into the given compound is to be predicted.

Concept introduction: The aldehyde group of aldoses oxidizes to carboxylic acid group in presence of bromine water to form aldonic acids. The hydroxyl groups of monosaccharides are converted into the ester groups in presence of base and acetic anhydride or acetyl chloride.

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Answer 3

Question

Chapter 28, Problem 28.55P

Interpretation Introduction

(a)

Interpretation: The conversion of D-glucose into the given compound is to be predicted.

Concept introduction: The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide. Glycosidic linkages are hydrolyzed in presence of acid to form cyclic hemiacetal and corresponding alcohol.

Interpretation Introduction

(b)

Interpretation: The conversion of D-glucose into the given compound is to be predicted.

Concept introduction: The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide. The carbonyl group of aldoses can be reduced to alcohol using metal hydrides.

Interpretation Introduction

(c)

Interpretation: The conversion of D-glucose into the given compound is to be predicted.

Concept introduction: The aldehyde group of aldoses oxidizes to carboxylic acid group in presence of bromine water to form aldonic acids. The hydroxyl groups of monosaccharides are converted into the ester groups in presence of base and acetic anhydride or acetyl chloride.

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Answer 4

Question

Chapter 28, Problem 28.55P

Interpretation Introduction

(a)

Interpretation: The conversion of D-glucose into the given compound is to be predicted.

Concept introduction: The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide. Glycosidic linkages are hydrolyzed in presence of acid to form cyclic hemiacetal and corresponding alcohol.

Interpretation Introduction

(b)

Interpretation: The conversion of D-glucose into the given compound is to be predicted.

Concept introduction: The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide. The carbonyl group of aldoses can be reduced to alcohol using metal hydrides.

Interpretation Introduction

(c)

Interpretation: The conversion of D-glucose into the given compound is to be predicted.

Concept introduction: The aldehyde group of aldoses oxidizes to carboxylic acid group in presence of bromine water to form aldonic acids. The hydroxyl groups of monosaccharides are converted into the ester groups in presence of base and acetic anhydride or acetyl chloride.

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Answer 5

Chapter 28, Problem 28.55P

Interpretation Introduction

(a)

Interpretation: The conversion of D-glucose into the given compound is to be predicted.

Concept introduction: The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide. Glycosidic linkages are hydrolyzed in presence of acid to form cyclic hemiacetal and corresponding alcohol.

Interpretation Introduction

(b)

Interpretation: The conversion of D-glucose into the given compound is to be predicted.

Concept introduction: The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide. The carbonyl group of aldoses can be reduced to alcohol using metal hydrides.

Interpretation Introduction

(c)

Interpretation: The conversion of D-glucose into the given compound is to be predicted.

Concept introduction: The aldehyde group of aldoses oxidizes to carboxylic acid group in presence of bromine water to form aldonic acids. The hydroxyl groups of monosaccharides are converted into the ester groups in presence of base and acetic anhydride or acetyl chloride.

Answer 6

Chapter 28, Problem 28.55P

Interpretation Introduction

(a)

Interpretation: The conversion of D-glucose into the given compound is to be predicted.

Concept introduction: The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide. Glycosidic linkages are hydrolyzed in presence of acid to form cyclic hemiacetal and corresponding alcohol.

Answer 7

Chapter 28, Problem 28.55P

Interpretation Introduction

(a)

Interpretation: The conversion of D-glucose into the given compound is to be predicted.

Concept introduction: The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide. Glycosidic linkages are hydrolyzed in presence of acid to form cyclic hemiacetal and corresponding alcohol.

Answer 8

Interpretation Introduction

(b)

Interpretation: The conversion of D-glucose into the given compound is to be predicted.

Concept introduction: The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide. The carbonyl group of aldoses can be reduced to alcohol using metal hydrides.

Answer 9

Interpretation Introduction

(b)

Interpretation: The conversion of D-glucose into the given compound is to be predicted.

Concept introduction: The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide. The carbonyl group of aldoses can be reduced to alcohol using metal hydrides.

Answer 10

Interpretation Introduction

(c)

Interpretation: The conversion of D-glucose into the given compound is to be predicted.

Concept introduction: The aldehyde group of aldoses oxidizes to carboxylic acid group in presence of bromine water to form aldonic acids. The hydroxyl groups of monosaccharides are converted into the ester groups in presence of base and acetic anhydride or acetyl chloride.

Answer 11

Interpretation Introduction

(c)

Interpretation: The conversion of D-glucose into the given compound is to be predicted.

Concept introduction: The aldehyde group of aldoses oxidizes to carboxylic acid group in presence of bromine water to form aldonic acids. The hydroxyl groups of monosaccharides are converted into the ester groups in presence of base and acetic anhydride or acetyl chloride.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 28 - Prob. 28.1P Ch. 28 - Prob. 28.2P Ch. 28 - Label each stereogenic center as R or S. a. b. c....Ch. 28 - Convert the ball-and-stick model to a Fischer...Ch. 28 - Prob. 28.5P Ch. 28 - Prob. 28.6P Ch. 28 - Prob. 28.7P Ch. 28 - Prob. 28.8P Ch. 28 - Prob. 28.9P Ch. 28 - Prob. 28.10P

Solution Summary: The author explains how the conversion of D-glucose into the given compound is predicted.

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Chapter 28 Solutions