(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

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

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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A pdf file of your hand drawn, stepwise mechanisms for the reactions. For each reaction in the assignment, you must write each mechanism three times (there are 10 reactions, so 30 mechanisms). (A) do the work on a tablet and save as a pdf., it is expected to write each mechanism out and NOT copy and paste the mechanism after writing it just once. Everything should be drawn out stepwise and every bond that is formed and broken in the process of the reaction, and is expected to see all relevant lone pair electrons and curved arrows.

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Answer 2

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

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

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

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

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

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