The number of carbons in D − glucose which do not have a hydroxyl group directly attached to it has to be stated. Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

Question

Does trehalose (Problem 20.68) have an acetal grouping? A hemiacetal grouping? Do you expect trehalose to be a reducing or nonreducing sugar? Classify the linkage between the two monosaccharides.

Answer 1

Question

Chapter 18, Problem 18.70EP

(a)

Interpretation Introduction

Interpretation: The number of carbons in D−glucose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

(b)

Interpretation Introduction

Interpretation: The number of carbons in D−galactose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

(c)

Interpretation Introduction

Interpretation: The number of carbons in D−fructose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

(d)

Interpretation Introduction

Interpretation: The number of carbons in D−ribose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

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Does trehalose (Problem 20.68) have an acetal grouping? A hemiacetal grouping? Do you expect trehalose to be a reducing or nonreducing sugar? Classify the linkage between the two monosaccharides.

An unknown trisaccharide was treated with dimethyl sulfate which adds a methyl group to every free OH group. It was then subjected to acid hydrolysis (to break glycoside bonds). The products were 23, 4, 6-tetra-O-methylgalactosc, 23,4-ui-O methyl glucose, and 2,3.6-tri-O methylglucose. Treatment of the intact trisaccharide with 0(1 6)-gaiactosidase yielded galactose and a saccharide. Treatment of this disaccharide with a(l 4)-glucosidase yielded D glucose. Draw the structure of this trisaccharide and give its systematic name.

In the monosaccharide derivatives known as sugar alcohols, the carbonyl oxygen is reduced to a hydroxyl group. For example, D-glyceraldehyde can be reduced to glycerol. However, this sugar alcohol is no longer designated D or L. Why?

Answer 2

Question

Chapter 18, Problem 18.70EP

(a)

Interpretation Introduction

Interpretation: The number of carbons in D−glucose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

(b)

Interpretation Introduction

Interpretation: The number of carbons in D−galactose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

(c)

Interpretation Introduction

Interpretation: The number of carbons in D−fructose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

(d)

Interpretation Introduction

Interpretation: The number of carbons in D−ribose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

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Answer 3

Question

Chapter 18, Problem 18.70EP

(a)

Interpretation Introduction

Interpretation: The number of carbons in D−glucose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

(b)

Interpretation Introduction

Interpretation: The number of carbons in D−galactose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

(c)

Interpretation Introduction

Interpretation: The number of carbons in D−fructose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

(d)

Interpretation Introduction

Interpretation: The number of carbons in D−ribose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

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Answer 4

Question

Chapter 18, Problem 18.70EP

(a)

Interpretation Introduction

Interpretation: The number of carbons in D−glucose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

(b)

Interpretation Introduction

Interpretation: The number of carbons in D−galactose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

(c)

Interpretation Introduction

Interpretation: The number of carbons in D−fructose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

(d)

Interpretation Introduction

Interpretation: The number of carbons in D−ribose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

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Answer 5

Chapter 18, Problem 18.70EP

(a)

Interpretation Introduction

Interpretation: The number of carbons in D−glucose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

(b)

Interpretation Introduction

Interpretation: The number of carbons in D−galactose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

(c)

Interpretation Introduction

Interpretation: The number of carbons in D−fructose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

(d)

Interpretation Introduction

Interpretation: The number of carbons in D−ribose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

Answer 6

Chapter 18, Problem 18.70EP

(a)

Interpretation Introduction

Interpretation: The number of carbons in D−glucose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

Answer 7

Chapter 18, Problem 18.70EP

(a)

Interpretation Introduction

Interpretation: The number of carbons in D−glucose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

Answer 8

(b)

Interpretation Introduction

Interpretation: The number of carbons in D−galactose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

Answer 9

(b)

Interpretation Introduction

Interpretation: The number of carbons in D−galactose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

Answer 10

(c)

Interpretation Introduction

Interpretation: The number of carbons in D−fructose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

Answer 11

(c)

Interpretation Introduction

Interpretation: The number of carbons in D−fructose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

Answer 12

(d)

Interpretation Introduction

Interpretation: The number of carbons in D−ribose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

Answer 13

(d)

Interpretation Introduction

Interpretation: The number of carbons in D−ribose which do not have a hydroxyl group directly attached to it has to be stated.

Concept introduction: Open chain structures of monosaccharides which contain five or more carbon atoms exist in equilibrium with two cyclic structures. These cyclic structures are the dominating forms at equilibrium. The carbonyl group in the open-chain structure of monosaccharide reacts intramolecularly with a hydroxyl group which results in the formation of cyclic forms. These cyclic compounds are called cyclic hemiacetals.

Answer 14

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Answer 25

Ch. 18.1 - In terms of mass percent, which of the following...Ch. 18.1 - Which of the following is the most abundant type...Ch. 18.2 - Which of the following statements concerning the...Ch. 18.2 - Prob. 2QQ Ch. 18.3 - Prob. 1QQ Ch. 18.3 - Prob. 2QQ Ch. 18.3 - Which of the following is not a possible value for...Ch. 18.3 - The complete hydrolysis of a polysaccharide...Ch. 18.4 - Prob. 1QQ Ch. 18.4 - Prob. 2QQ

Solution Summary: The author explains that open chain structures of monosaccharides contain five or more carbon atoms in equilibrium with two cyclic structures. The carbonyl group reacts intramolecularly with a hydroxyl

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Chapter 18 Solutions