Organic Chemistry
Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 28, Problem 28.66P
Interpretation Introduction

(a)

Interpretation: The glycosidic linkages of the stachyose are to be labeled.

Concept introduction: Monosaccharides are the small units of simple sugars. Polysaccharides are made up of small units of monosaccharides. These small units are joined together by glycoside linkage.

Expert Solution
Check Mark

Answer to Problem 28.66P

The red colored oxygen atoms are a part of glycosic linkages as hown below.

Organic Chemistry, Chapter 28, Problem 28.66P , additional homework tip  1

Figure 1

Explanation of Solution

The structure of stachyose,

Organic Chemistry, Chapter 28, Problem 28.66P , additional homework tip  2

Figure 1

The acetals containing alkoxy groups attached to anomeric carbons in the stachyose represent the glycosidic linkages. The red colored oxygen atoms are a part of glycosic linkages.

Conclusion

The glycosidic linkages of the stachyose are shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: Each glycosidic linkages of the stachyose are to be classified as α or β and the numbers are to be used to designate the locations between two rings.

Concept introduction: Monosaccharides are the small units of simple sugars. Polysaccharides are made up of small units of monosaccharides. These small units are joined together by glycoside linkage.

Expert Solution
Check Mark

Answer to Problem 28.66P

The glycosidic linkage I is α 16, II is α 16 and III is α 12β as shown below.

Organic Chemistry, Chapter 28, Problem 28.66P , additional homework tip  3

Figure 1

Explanation of Solution

The structure of stachyose,

Organic Chemistry, Chapter 28, Problem 28.66P , additional homework tip  4

Figure 1

The glycosidic linkages which are composed of alkoxy group above the plane are β-glycosidic linkages and which are composed of alkoxy groups below the plane are α-glycosidic linkages. The glycosidic linkage I is α 16, II is α 16 and III is α2β.

Conclusion

The glycosidic linkage I is α 16, II is α 16 and III is α 12β shown in Figure 1.

Interpretation Introduction

(c)

Interpretation: The products formed on hydrolysis of stachyose are to be predicted.

Concept introduction: Glycosidic linkages are hydrolyzed in presence of acid to form cyclic hemiacetal and corresponding alcohol. Acetals in the presence of acid undergo hydrolysis to form cyclic hemiacetals.

Expert Solution
Check Mark

Answer to Problem 28.66P

The products formed on hydrolysis of stachyose are,

Organic Chemistry, Chapter 28, Problem 28.66P , additional homework tip  5

Figure 2

Explanation of Solution

On acidic hydrolysis of stachyose, the glycosidic linkages are cleaved to form the four products. The corresponding chemical reaction is shown below.

Organic Chemistry, Chapter 28, Problem 28.66P , additional homework tip  6

Figure 3

The products formed are α-D-glucose, β-D-fructose and two units of α-D-galactose.

Interpretation Introduction

(d)

Interpretation: The validation to the corresponding fact that whether stachyose is reducing sugar or not is to be stated.

Concept introduction: The reducing sugars contain hemiacetal and they undergo mutarotation. These sugars are in equilibrium with cyclic monosaccharide forms.

Expert Solution
Check Mark

Answer to Problem 28.66P

Stachyose is not a reducing sugar.

Explanation of Solution

The given tetrasaccharide stachyose does not contain any hemiacetal and does not undergo mutarotation. Thus, the given tetrasaccharide is not a reducing sugar.

Conclusion

The product formed on treatment of stachyose with excess CH3I, Ag2O is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation: The product formed on treatment of stachyose with excess CH3I, Ag2O is to be determined.

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.

Expert Solution
Check Mark

Answer to Problem 28.66P

The product formed on treatment of stachyose with excess CH3I, Ag2O is,

Organic Chemistry, Chapter 28, Problem 28.66P , additional homework tip  7

Figure 4

Explanation of Solution

On treatment of stachyose with excess CH3I, Ag2O, the hydroxyl groups of stachyose are converted into the methoxy groups. The corresponding chemical reaction is shown below.

Organic Chemistry, Chapter 28, Problem 28.66P , additional homework tip  8

Figure 5

Conclusion

The product formed on treatment of stachyose with excess CH3I, Ag2O is shown in Figure 4.

Interpretation Introduction

(f)

Interpretation: The product formed on treatment of product in (e) with H3O+ is to be determined.

Concept introduction: Glycosidic linkages are hydrolyzed in presence of acid to form cyclic hemiacetal and corresponding alcohol. Acetals in the presence of acid undergo hydrolysis to form cyclic hemiacetals.

Expert Solution
Check Mark

Answer to Problem 28.66P

The products formed on treatment of product in (e) with H3O+ are,

Organic Chemistry, Chapter 28, Problem 28.66P , additional homework tip  9

Figure 6

Explanation of Solution

On acidic hydrolysis of the given compound, the glycosidic linkages are cleaved to form the four products. The corresponding chemical reaction is shown below.

Organic Chemistry, Chapter 28, Problem 28.66P , additional homework tip  10

Figure 7

Conclusion

The products formed on treatment of product in (e) with H3O+ are shown in Figure 6.

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Chapter 28 Solutions

Organic Chemistry

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