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Like glucose, galactose mutarotates when it dissolves in water. The specific rotation of -D-galactopyranoseis +150.70 , and that of the anomer is +52.80 . When either of the pure anomers dissolves in water, the specific rotation gradually changes to +80.20. Determine the percentages of the two anomers present at equilibrium.

Short Answer

Expert verified

anomer=28%andanomer=72%

Step by step solution

01

Mutarotation

A spontaneous change in the specific rotation of a solution of an optically active compound is known as mutarotation. This implies that the two samples are different but in solution they form an equilibrium mixture.

02

Anomers

The diastereomers resulting from cyclisation are known as anomers. They differ only in the configuration around first carbon (C1) which is referred to as the anomeric carbon (hemiacetal carbon atom).

03

Calculation

If the fraction of galactose present as the anomer is role="math" localid="1664865398062" =+150.70 is a, the fraction present as the anomer is =+52.80, and the specific rotation of the mixture is +80.2, then we can write as:

role="math" localid="1664865861024" a+150.70+b+52.80=+80.20

The fraction present as the anomer (a) plus the fraction present as anomer (b) should account for all the galactose.

a+b = 1 or we can write b = 1-a

Now,

a+150.70+b+52.80=+80.20a+150.70+1-a52.80=80.20a150.70+52.80-a52.80=80.20a150.70-52.80=80.20-52.80a97.90=27.40a=27.4097.90a=0.28

So,

b=1-a=1-0.28=0.72

Hence, the amounts of two anomers present at equilibrium are anomer = 28% and anomer = 72%.

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Most popular questions from this chapter

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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(a) methylDgalactopyranoside (b) Lidopyranose (an aldohexose)

(c) Dallopyranose (d) Lribofuranoside

(e) (f)

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Is gentiobiose a reducing sugar? Does it mutarotate? Explain your reasoning.

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