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Concept explainers
(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.
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Answer to Problem 28.66P
The red colored oxygen atoms are a part of glycosic linkages as hown below.
Figure 1
Explanation of Solution
The structure of stachyose,
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.
The glycosidic linkages of the stachyose are shown in Figure 1.
(b)
Interpretation: Each glycosidic linkages of the stachyose are to be classified as
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.
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Answer to Problem 28.66P
The glycosidic linkage
Figure 1
Explanation of Solution
The structure of stachyose,
Figure 1
The glycosidic linkages which are composed of alkoxy group above the plane are
The glycosidic linkage
(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.
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Answer to Problem 28.66P
The products formed on hydrolysis of stachyose are,
Figure 2
Explanation of Solution
On acidic hydrolysis of stachyose, the glycosidic linkages are cleaved to form the four products. The corresponding
Figure 3
The products formed are
(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.
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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.
The product formed on treatment of stachyose with excess
(e)
Interpretation: The product formed on treatment of stachyose with excess
Concept introduction: The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and
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Answer to Problem 28.66P
The product formed on treatment of stachyose with excess
Figure 4
Explanation of Solution
On treatment of stachyose with excess
Figure 5
The product formed on treatment of stachyose with excess
(f)
Interpretation: The product formed on treatment of product in (e) with
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.
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Answer to Problem 28.66P
The products formed on treatment of product in (e) with
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.
Figure 7
The products formed on treatment of product in (e) with
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Chapter 28 Solutions
ORGANIC CHEMISTRY
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