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Chapter 23: Q36P (page 1236)

Draw the structure of the individual mutarotating 伪 and 尾 anomers of maltose.

Short Answer

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Draw the structure of the individual mutarotating 伪 and 尾 anomers of maltose.

Step by step solution

01

A concept:

Maltose is a disaccharide which is obtained as a result of partial hydrolysis of starch by an enzyme known as diastase.

Hydrolysis of maltose in presence of dilute acids yields only D-glucose which implies that the maltose molecule is made up of two glucose units. Two glucose units in maltose are linked by an 伪 glycosidic linkage between C1 of one unit and C4 of another unit. Maltose is known to exist both in 伪 and 尾 forms, each of which exhibits mutarotation.

02

Draw the structure:

The structures of 伪 and 尾 anomers of maltose are shown below:

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Most popular questions from this chapter

Draw and name the enantiomers of the sugars shown in Figure 23-2. Give the relative configuration (D or L) and the sign of the rotation in each case.

The carbonyl group in D-galactose may be isomerized from C1 to C2 by brief treatment with dilute base (by enediol rearrangement, Section 23-7). The product is the C4 epimer of fructose. Draw the furanose structure of the product.

(a) Show the product that results when fructose is treated with an excess of methyl iodide and silver oxide.

(b) Show what happens when the product of part (a) is hydrolyzed using dilute acid.

(c) What do the results of parts (a) and (b) imply about the hemiacetal structure of fructose?

Predict the products obtained when D-galactose reacts with each reagent.

(a) Br2 and H2O

(b) NaOH,H2O

(c)CH3OH, H+

(d) Ag(NH3)+2OH+

(e) H2, Ni

(f) excess Ac2O and pyridine

(g) excess CH3I ,Ag2O

(h) NaBH4

(i) Br2 , H2O then H2O2 and Fe2(SO4)3

(j) (1) KCN/HCN; (2) H2 Pd/BaSO4; (3) H3O+

(k)excess HIO4

After a series of Kiliani鈥揊ischer syntheses on (+)-glyceraldehyde, an unknown sugar is isolated from the reaction mixture. The following experimental information is obtained:

(1) Molecular formula C6H12O6

(2) Undergoes mutarotation.

(3) Reacts with bromine water to give an aldonic acid.

(4) Reacts with HNO3 to give an optically active aldaric acid.

(5) Ruff degradation followed by HNO3 oxidation gives an optically inactive aldaric acid. (6) Two Ruff degradations followed by HNO3 oxidation give meso-tartaric acid.

(7) When the original sugar is treated with CH3I and Ag2O, a pentamethyl derivative is formed. Hydrolysis gives a tetramethyl derivative with a free hydroxy group on C5.

(a) Draw a Fischer projection for the open-chain form of this unknown sugar. Use Figure 23-3 to name the sugar.

(b) Draw the most stable conform

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