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Chapter 19: Q52E (page 648)

When crystals of pure α-glucose are dissolved in water, isomerization occurs slowly to produce β-glucose. Propose a mechanism for isomerization.

Short Answer

Expert verified

The Mutarotation is differ from specific rotation, due to the change in equilibrium between alpha and beta anomeric forms, in the aqueous solution.

Only those carbohydrates show mutarotation which is hemiacetal or hemiketal.

Step by step solution

01

Mutarotation

The Mutarotation is differ from specific rotation, due to the change in equilibrium between alpha and beta anomeric forms, in the aqueous solution.

Only those carbohydrates show mutarotation which is hemiacetal or hemiketal.

02

Mechanism for conversion of alpha glucose to beta glucose

In the first step lone pair of oxygen of hydroxyl get delocalized and the bond between carbon and oxygen gets a break. Further, the rotation of the bond is observed as shown in the following mechanism. In the next step negatively charge oxygen attacks the carbon and further rearrangement.

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Most popular questions from this chapter

Primary amines react with esters to yield amides: RCO2R' + R"NH2 →RCONHR" + R'OH . Propose a mechanism for the following reaction of an a b-unsaturated ester.

Show the products you would obtain by acid-catalyzed reaction of cyclohexanonewith ethylamine, CH3CH2NH2, and with diethylamine, (CH3CH2)2NH.

Propose structures for ketones or aldehydes that have the following 1H

NMR spectra:

(a) C4H7ClO

IR: 1715 cm-1

(b)C7H14O

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When glucose (Problem 19-52) is treated with NaBH4 , reaction occurs to yield sorbitol, a polyalcohol commonly used as a food additive. Show how this reduction occurs.

It is not uncommon for organic chemists to prepare acetals by an exchange-type process known as transacetalization. Predict the product(s) and show the mechanism for the transacetalization reactions below.

a.

b.
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