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Chapter 28: Question 28.26 (page 1133)

What aldoses are formed when the following aldoses are subjected to the Kiliani-Fischer synthesis: (a) D-threose; (b) D-ribose; (c) D-galactose

Short Answer

Expert verified

Answer

(a.)

(b.)

(c.)

Step by step solution

01

Aldoses

The test used to distinguish aldoses from ketoses is Seliwanoff鈥檚 test. It comprises a dehydration reaction that happens fast in aldoses and slows in ketoses.

02

Kiliani-Fischer synthesis

The carbohydrate chain lengthens in the process of Kiliani Fischer synthesis. In this process, a carbon atom is incorporated into the aldose's aldehyde end. This leads to the formation of two epimers at C2.

03

Different aldoses formed on Kiliani-Fischer synthesis

(a) The different aldoses formed on the Kiliani Fischer synthesis of D-threose are D-xylose and D-lyxose. The structures can be given as:

Kiliani Fischer synthesis of D-threose

(b) The different aldoses formed on the Kiliani Fischer synthesis of D-ribose are D-altrose and D-allose. The structures are given as:

Kiliani Fischer synthesis of D-ribose

(c) The different aldoses formed on the Kiliani Fischer synthesis of D-galactose comprise seven carbons. The structures can be given as:

Kiliani Fischer synthesis of D-galactose

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Most popular questions from this chapter

Draw the products formed when 尾-D galactose is treated with each reagent.

a.data-custom-editor="chemistry" Ag2O+CH3I

b.data-custom-editor="chemistry" NAH+C6H5CH2Cl

c. The product in (b), then

d.data-custom-editor="chemistry" Theproductin(b.)andH3O+

e. data-custom-editor="chemistry" Ac2O+pyridine

f. data-custom-editor="chemistry" C6H5COCl+pyridine

g. The product in (c), then data-custom-editor="chemistry" C6H5COCl+pyridine

What aglycon and monosaccharides are formed when salicin and solanine (Section 28.7C) are each hydrolyzed with aqueous acid?

(a)Label all the O atoms that are part of a glycoside in rebaudioside A. Rebaudioside A, marketed under the trade name Truvia, is a sweet glycoside obtained from the stevia plant, which has been used for centuries in Paraguay to sweeten foods. (b)The alcohol or phenol formed from the hydrolysis of glycoside is called an aglycon. What aglycon and monosaccharides are formed by the hydrolysis of rebaudioside A?

Draw the structure of a disaccharide formed from two mannose units joined by a 1-4鈫�伪glycosidic linkage.

Draw the structures of the nucleosides formed from each of the following components: (a) ribose + uracil; (b) 2-deoxyribose + guanine.
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