Organic And Biological Chemistry
Organic And Biological Chemistry
7th Edition
ISBN: 9781305081079
Author: STOKER, H. Stephen (howard Stephen)
Publisher: Cengage Learning,
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Chapter 7, Problem 7.109EP

(a)

Interpretation Introduction

Interpretation: The name of the given compound has to be stated.

Concept introduction: In a cyclic monosaccharide, the replacement of an −OH group of the hemiacetal carbon by an −OR group results in the formation of an acetal.  The acetal formed is known as a glycoside.  The naming of Glycosides is done by first writing the alkyl substituent of −OR group attached to the hemiacetal carbon, followed by the name of monosaccharide involved, with the suffix-ide appended to it.

(a)

Expert Solution
Check Mark

Answer to Problem 7.109EP

The name of the given structure is methyl-α-D-alloside.

Explanation of Solution

The Fisher projection formula for D-allose is,

Organic And Biological Chemistry, Chapter 7, Problem 7.109EP , additional homework tip 1

The structure given in Problem 18-103 is,

Organic And Biological Chemistry, Chapter 7, Problem 7.109EP , additional homework tip 2

The above structure is the cyclic form of monosaccharide D-allose.  Both the −CH2OH group and −OCH3 group point in the opposite direction.  Therefore, the configuration is α.  In a cyclic monosaccharide, the replacement of an −OH group of the hemiacetal carbon by an −OR group results in the formation of an acetal.  The acetal formed is known as a glycoside.  The naming of Glycosides is done by first writing the alkyl substituent of −OR group attached to the hemiacetal carbon, followed by the name of monosaccharide involved, with the suffix-ide appended to it.  In the above structure, an −OCH3 group is attached to the hemiacetal carbon.  Therefore, the name of the given structure is methyl-α-D-alloside.

(b)

Interpretation Introduction

Interpretation: The name of the given compound has to be stated.

Concept introduction: In a cyclic monosaccharide, the replacement of an −OH group of the hemiacetal carbon by an −OR group results in the formation of an acetal.  The acetal formed is known as a glycoside.  The naming of Glycosides is done by first writing the alkyl substituent of −OR group attached to the hemiacetal carbon, followed by the name of monosaccharide involved, with the suffix-ide appended to it.

(b)

Expert Solution
Check Mark

Answer to Problem 7.109EP

The name of the given structure is ethyl-β-D-altroside.

Explanation of Solution

The Fisher projection formula for D-altrose is,

Organic And Biological Chemistry, Chapter 7, Problem 7.109EP , additional homework tip 3

The structure given in Problem 18-103 is,

Organic And Biological Chemistry, Chapter 7, Problem 7.109EP , additional homework tip 4

The above structure is the cyclic form of monosaccharide D- altrose. Both the −CH2OH group and −OCH2CH3 group point in the same direction.  Therefore, the configuration is β.  In a cyclic monosaccharide, the replacement of an −OH group of the hemiacetal carbon by an −OR group results in the formation of an acetal.  The acetal formed is known as a glycoside.  The naming of Glycosides is done by first writing the alkyl substituent of −OR group attached to the hemiacetal carbon, followed by the name of monosaccharide involved, with the suffix-ide appended to it.  In the above structure, an −OCH2CH3 group is attached to the hemiacetal carbon.  Therefore, the name of the given structure is ethyl-β-D-altroside.

(c)

Interpretation Introduction

Interpretation: The name of the given compound has to be stated.

Concept introduction: In a cyclic monosaccharide, the replacement of an −OH group of the hemiacetal carbon by an −OR group results in the formation of an acetal.  The acetal formed is known as a glycoside.  The naming of Glycosides is done by first writing the alkyl substituent of −OR group attached to the hemiacetal carbon, followed by the name of monosaccharide involved, with the suffix-ide appended to it.

(c)

Expert Solution
Check Mark

Answer to Problem 7.109EP

The name of the given structure is ethyl-α-D-fructoside.

Explanation of Solution

The Fisher projection formula for D-fructose is,

Organic And Biological Chemistry, Chapter 7, Problem 7.109EP , additional homework tip 5

The structure given in Problem 18-103 is,

Organic And Biological Chemistry, Chapter 7, Problem 7.109EP , additional homework tip 6

The above structure is the cyclic form of monosaccharide D-fructose. Both the −CH2OH group and −OCH2CH3 group point in the opposite direction.  Therefore, the configuration is α.  In a cyclic monosaccharide, the replacement of an −OH group of the hemiacetal carbon by an −OR group results in the formation of an acetal.  The acetal formed is known as a glycoside.  The naming of Glycosides is done by first writing the alkyl substituent of −OR group attached to the hemiacetal carbon, followed by the name of monosaccharide involved, with the suffix-ide appended to it.  In the above structure, an −OCH2CH3 group is attached to the hemiacetal carbon.  Therefore, the name of the given structure is ethyl-α-D-fructoside.

(d)

Interpretation Introduction

Interpretation: The name of the given compound has to be stated.

Concept introduction: In a cyclic monosaccharide, the replacement of an −OH group of the hemiacetal carbon by an −OR group results in the formation of an acetal.  The acetal formed is known as a glycoside.  The naming of Glycosides is done by first writing the alkyl substituent of −OR group attached to the hemiacetal carbon, followed by the name of monosaccharide involved, with the suffix-ide appended to it.

(d)

Expert Solution
Check Mark

Answer to Problem 7.109EP

The name of the given structure is methyl-β-D-glucoside.

Explanation of Solution

The Fisher projection formula for D-glucose is,

Organic And Biological Chemistry, Chapter 7, Problem 7.109EP , additional homework tip 7

The structure given in Problem 18-103 is,

Organic And Biological Chemistry, Chapter 7, Problem 7.109EP , additional homework tip 8

The above structure is the cyclic form of monosaccharide D-glucose. Both the −CH2OH group and −OCH3 group point in the same direction.  Therefore, the configuration is β.  In a cyclic monosaccharide, the replacement of an −OH group of the hemiacetal carbon by an −OR group results in the formation of an acetal.  The acetal formed is known as a glycoside.  The naming of Glycosides is done by first writing the alkyl substituent of −OR group attached to the hemiacetal carbon, followed by the name of monosaccharide involved, with the suffix-ide appended to it.  In the above structure, an −OCH3 group is attached to the hemiacetal carbon.  Therefore, the name of the given structure is methyl-β-D-glucoside.

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Chapter 7 Solutions

Organic And Biological Chemistry

Ch. 7.1 - In terms of mass percent, which of the following...Ch. 7.1 - Which of the following is the most abundant type...Ch. 7.2 - Which of the following statements concerning the...Ch. 7.2 - Prob. 2QQCh. 7.3 - Prob. 1QQCh. 7.3 - Prob. 2QQCh. 7.3 - Which of the following is not a possible value for...Ch. 7.3 - The complete hydrolysis of a polysaccharide...Ch. 7.4 - Prob. 1QQCh. 7.4 - Prob. 2QQ
Ch. 7.4 - Prob. 3QQCh. 7.4 - Prob. 4QQCh. 7.5 - Prob. 1QQCh. 7.5 - Prob. 2QQCh. 7.6 - Prob. 1QQCh. 7.6 - Which of the following Fischer projection formulas...Ch. 7.6 - Prob. 3QQCh. 7.6 - Prob. 4QQCh. 7.7 - Prob. 1QQCh. 7.7 - Prob. 2QQCh. 7.8 - Prob. 1QQCh. 7.8 - Which of the following statements about...Ch. 7.8 - Prob. 3QQCh. 7.9 - Prob. 1QQCh. 7.9 - Prob. 2QQCh. 7.9 - Prob. 3QQCh. 7.9 - In which of the following pairs of monosaccharides...Ch. 7.9 - In which of the following pairs of monosaccharides...Ch. 7.10 - Prob. 1QQCh. 7.10 - Which of the following structures represents a...Ch. 7.10 - Prob. 3QQCh. 7.10 - Prob. 4QQCh. 7.10 - Prob. 5QQCh. 7.11 - Prob. 1QQCh. 7.11 - Which of the following is the correct Haworth...Ch. 7.12 - Prob. 1QQCh. 7.12 - Prob. 2QQCh. 7.12 - Prob. 3QQCh. 7.12 - Prob. 4QQCh. 7.12 - Prob. 5QQCh. 7.13 - Which of the following disaccharides contains...Ch. 7.13 - Which of the following disaccharides will produce...Ch. 7.13 - In which of the following disaccharides is the...Ch. 7.13 - In which of the following pairs of disaccharides...Ch. 7.13 - Which of the following disaccharides is not a...Ch. 7.13 - The terms milk sugar and table sugar apply,...Ch. 7.14 - Prob. 1QQCh. 7.14 - Prob. 2QQCh. 7.15 - Which of the following statements about...Ch. 7.15 - Prob. 2QQCh. 7.16 - Which of the following storage polysaccharides has...Ch. 7.16 - Prob. 2QQCh. 7.16 - Prob. 3QQCh. 7.16 - Prob. 4QQCh. 7.17 - Prob. 1QQCh. 7.17 - Which of the following statements about cellulose...Ch. 7.17 - Chitin is a polysaccharide in which the...Ch. 7.18 - Which of the following statements about the...Ch. 7.18 - Which of the following statements about the...Ch. 7.19 - Which of the following is not classified as a...Ch. 7.19 - Prob. 2QQCh. 7.20 - Which of the following types of compounds are...Ch. 7.20 - Which of the following is not a biochemical...Ch. 7 - Prob. 7.1EPCh. 7 - Prob. 7.2EPCh. 7 - Prob. 7.3EPCh. 7 - Prob. 7.4EPCh. 7 - Prob. 7.5EPCh. 7 - Prob. 7.6EPCh. 7 - Prob. 7.7EPCh. 7 - Prob. 7.8EPCh. 7 - Prob. 7.9EPCh. 7 - Prob. 7.10EPCh. 7 - Prob. 7.11EPCh. 7 - Prob. 7.12EPCh. 7 - Prob. 7.13EPCh. 7 - Prob. 7.14EPCh. 7 - Prob. 7.15EPCh. 7 - Prob. 7.16EPCh. 7 - Prob. 7.17EPCh. 7 - Prob. 7.18EPCh. 7 - Prob. 7.19EPCh. 7 - Prob. 7.20EPCh. 7 - Prob. 7.21EPCh. 7 - Prob. 7.22EPCh. 7 - Prob. 7.23EPCh. 7 - Prob. 7.24EPCh. 7 - Prob. 7.25EPCh. 7 - Indicate whether or not each of the molecules in...Ch. 7 - Prob. 7.27EPCh. 7 - Prob. 7.28EPCh. 7 - Prob. 7.29EPCh. 7 - Prob. 7.30EPCh. 7 - Prob. 7.31EPCh. 7 - Prob. 7.32EPCh. 7 - Prob. 7.33EPCh. 7 - Prob. 7.34EPCh. 7 - Prob. 7.35EPCh. 7 - Draw the Fischer projection formula for each of...Ch. 7 - Prob. 7.37EPCh. 7 - Prob. 7.38EPCh. 7 - Prob. 7.39EPCh. 7 - Prob. 7.40EPCh. 7 - Prob. 7.41EPCh. 7 - Prob. 7.42EPCh. 7 - Prob. 7.43EPCh. 7 - Prob. 7.44EPCh. 7 - Prob. 7.45EPCh. 7 - Prob. 7.46EPCh. 7 - Prob. 7.47EPCh. 7 - Prob. 7.48EPCh. 7 - Prob. 7.49EPCh. 7 - Prob. 7.50EPCh. 7 - Prob. 7.51EPCh. 7 - Prob. 7.52EPCh. 7 - Prob. 7.53EPCh. 7 - Prob. 7.54EPCh. 7 - Prob. 7.55EPCh. 7 - Prob. 7.56EPCh. 7 - Prob. 7.57EPCh. 7 - Prob. 7.58EPCh. 7 - Prob. 7.59EPCh. 7 - Prob. 7.60EPCh. 7 - Prob. 7.61EPCh. 7 - Prob. 7.62EPCh. 7 - Prob. 7.63EPCh. 7 - Prob. 7.64EPCh. 7 - Prob. 7.65EPCh. 7 - Prob. 7.66EPCh. 7 - Prob. 7.67EPCh. 7 - Prob. 7.68EPCh. 7 - Prob. 7.69EPCh. 7 - Prob. 7.70EPCh. 7 - Prob. 7.71EPCh. 7 - Prob. 7.72EPCh. 7 - Prob. 7.73EPCh. 7 - Prob. 7.74EPCh. 7 - Prob. 7.75EPCh. 7 - Prob. 7.76EPCh. 7 - Prob. 7.77EPCh. 7 - Prob. 7.78EPCh. 7 - Prob. 7.79EPCh. 7 - Prob. 7.80EPCh. 7 - Prob. 7.81EPCh. 7 - Prob. 7.82EPCh. 7 - Prob. 7.83EPCh. 7 - Prob. 7.84EPCh. 7 - Prob. 7.85EPCh. 7 - Prob. 7.86EPCh. 7 - Prob. 7.87EPCh. 7 - Prob. 7.88EPCh. 7 - Prob. 7.89EPCh. 7 - Prob. 7.90EPCh. 7 - Prob. 7.91EPCh. 7 - Prob. 7.92EPCh. 7 - Prob. 7.93EPCh. 7 - Prob. 7.94EPCh. 7 - Prob. 7.95EPCh. 7 - Prob. 7.96EPCh. 7 - Prob. 7.97EPCh. 7 - Classify each of the glucose derivatives in...Ch. 7 - Prob. 7.99EPCh. 7 - Prob. 7.100EPCh. 7 - Prob. 7.101EPCh. 7 - Prob. 7.102EPCh. 7 - Prob. 7.103EPCh. 7 - Prob. 7.104EPCh. 7 - Prob. 7.105EPCh. 7 - Prob. 7.106EPCh. 7 - Prob. 7.107EPCh. 7 - Prob. 7.108EPCh. 7 - Prob. 7.109EPCh. 7 - Prob. 7.110EPCh. 7 - Prob. 7.111EPCh. 7 - Prob. 7.112EPCh. 7 - Prob. 7.113EPCh. 7 - Prob. 7.114EPCh. 7 - Prob. 7.115EPCh. 7 - Prob. 7.116EPCh. 7 - Prob. 7.117EPCh. 7 - Prob. 7.118EPCh. 7 - Prob. 7.119EPCh. 7 - Prob. 7.120EPCh. 7 - Prob. 7.121EPCh. 7 - Prob. 7.122EPCh. 7 - Prob. 7.123EPCh. 7 - Prob. 7.124EPCh. 7 - Prob. 7.125EPCh. 7 - Prob. 7.126EPCh. 7 - Prob. 7.127EPCh. 7 - Prob. 7.128EPCh. 7 - Prob. 7.129EPCh. 7 - Prob. 7.130EPCh. 7 - Prob. 7.131EPCh. 7 - Prob. 7.132EPCh. 7 - Prob. 7.133EPCh. 7 - Prob. 7.134EPCh. 7 - Prob. 7.135EPCh. 7 - Prob. 7.136EPCh. 7 - Prob. 7.137EPCh. 7 - Prob. 7.138EPCh. 7 - Prob. 7.139EPCh. 7 - Prob. 7.140EPCh. 7 - Prob. 7.141EPCh. 7 - Prob. 7.142EPCh. 7 - Prob. 7.143EPCh. 7 - Prob. 7.144EPCh. 7 - Prob. 7.145EPCh. 7 - Prob. 7.146EPCh. 7 - Prob. 7.147EPCh. 7 - Prob. 7.148EPCh. 7 - Prob. 7.149EPCh. 7 - Prob. 7.150EPCh. 7 - Prob. 7.151EPCh. 7 - Prob. 7.152EPCh. 7 - 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