(a) What other sugar, if any, would give the same aldaric acid as D-talose when oxidized with nitric acid? (b) What other sugar, if any, would give the same aldaric acid as D-xylose when oxidized with nitric acid? (c) What other sugar, if any, would give the same aldaric acid as D-idose when oxidized with nitric acid?

Short Answer

Expert verified
a) D-galactose. b) D-lyxose. c) D-glucose.

Step by step solution

01

Understanding aldaric acids

Aldaric acids are dicarboxylic acids formed when both the aldehyde and primary alcohol groups of an aldose sugar are oxidized using nitric acid. This oxidation transforms the aldose into its corresponding aldaric acid.
02

Identifying D-talose oxidative product

When D-talose is oxidized with nitric acid, it forms an aldaric acid by converting the aldehyde group at C1 and the primary alcohol group at C6 into carboxyl groups. The same structural aldaric acid can be formed from a sugar that is a corresponding epimer at certain carbon positions.
03

Epimers of D-talose

D-talose has an epimer, D-galactose, which differs at carbon C-2. Oxidizing D-galactose will produce the same aldaric acid as D-talose. Thus, D-galactose is the other sugar that produces the same aldaric acid as D-talose when oxidized with nitric acid.
04

Identifying D-xylose oxidative product

Similar to the previous step, oxidize D-xylose to form the aldaric acid. An epimer with equivalent oxidation outcomes needs to be identified.
05

Epimer of D-xylose

D-lyxose is the sugar that differs at carbon C-3 from D-xylose. Oxidizing D-lyxose will produce the same aldaric acid as D-xylose. Hence, D-lyxose is the sugar producing the same aldaric acid as D-xylose when oxidized.
06

Identifying D-idose oxidative product

Perform the same analysis as done previously. Identify another sugar that will yield the same aldaric acid after oxidation.
07

Epimer of D-idose

D-glucose, which is an epimer at carbon C-2 of D-idose, will produce the same aldaric acid as D-idose when oxidized with nitric acid. Thus, D-glucose is the corresponding sugar for D-idose.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Oxidation of Aldoses
Aldaric acids are formed by the oxidation of aldose sugars. The process involves converting both the aldehyde group (found at the first carbon, C1) and the primary alcohol group (found at the last carbon, typically C6) into carboxyl groups. This transformation results in a dicarboxylic acid structure known as an aldaric acid.

Understanding this is crucial for solving problems related to aldaric acids.

For example, when D-talose is oxidized with nitric acid, the aldehyde group at C1 and the primary alcohol at C6 are both converted to carboxylic acids. This forms D-talose aldaric acid.

It is also important to know that different aldoses can produce the same aldaric acid if they differ only in the configuration of carbons that are not directly involved in the oxidation process.
Epimers in Sugars
Epimers are sugars that differ only in the configuration around one specific carbon atom. This small structural change can significantly impact the properties of the sugars.

For example, D-talose and D-galactose are epimers, differing only at the second carbon (C-2). When oxidized, both produce the same aldaric acid because the differences in configuration do not affect the aldehyde or primary alcohol groups that participate in oxidation.

Another example is D-xylose and D-lyxose which differ at the third carbon (C-3). Despite this difference, both sugars produce the same aldaric acid upon oxidation.

Finally, D-idose and D-glucose are epimers differing at carbon (C-2). Both generate the same aldaric acid because the oxidation process affects the aldehyde group at C1 and the primary alcohol at C6.
Dicarboxylic Acids from Sugars
Dicarboxylic acids, also known as aldaric acids, are formed during the oxidation of sugars. This oxidation process transforms sugars by converting both terminal functional groups, specifically the aldehyde at C1 and the alcohol at C6, into carboxyl groups.

The formation of dicarboxylic acids from sugars can be illustrated with specific examples. Take D-talose: oxidizing it yields a dicarboxylic acid. Similarly, oxidizing its epimer, D-galactose, results in the same dicarboxylic acid.

When D-xylose undergoes oxidation, it forms an aldaric acid, which is also produced by its epimer, D-lyxose. As for D-idose, oxidation results in a dicarboxylic acid identical to that produced from oxidizing D-glucose, its epimer.

Understanding how these sugars convert to dicarboxylic acids helps in predicting the products of oxidation reactions in carbohydrate chemistry.

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Most popular questions from this chapter

The anomeric effect is the observed increase in stabilization of electronegative groups in the \(\alpha\) position compared to the \(\beta\) position for D sugars in the pyranose form. One possible explanation for this increase in stabilization is hyperconjugation. Explain how hyperconjugation can be used to justify the anomeric effect.

(a) What sugar or sugars would result from the Ruff degradation applied to D-gulose? (b) What sugar or sugars would result from the KilianiFischer synthesis applied to D-lyxose?

The disaccharide maltose \(\left(\mathrm{C}_{12} \mathrm{H}_{22} \mathrm{O}_{11}\right)\) can be hydrolyzed in acid to two molecules of \(\mathrm{D}\)-glucose. It is also hydrolyzed by the enzyme maltase, a molecule known to cleave only \(\alpha\) - glycosidic linkages. Maltose can be oxidized by bromine in water to maltobionic acid (MBA; \(\mathrm{C}_{12} \mathrm{H}_{22} \mathrm{O}_{12}\) ). When MBA is treated with methyl iodide and base, followed by acid hydrolysis, the products are \(2,3,4,6\)-tetramethyl-Dglucopyranose and 2,3,5,6-tetramethyl-D-gluconic acid. Provide a three-dimensional structure for maltose and explain your reasoning.

Calculate the equilibrium ratio of \(\alpha\) - and \(\beta\)-D-glucopyranose from the specific rotations of the pure anomers \(\left(\alpha=+112^{\circ}, \beta=+18.7^{\circ}\right.\); equilibrium value \(=\) \(\left.+52.7^{\circ}\right)\). You might compare your calculation with the values given in Table 20.2.

Reduction of D-altrose with sodium borohydride in water gives an optically active molecule, D-altritol. However, the same procedure applied to D-allose gives an optically inactive product. Explain.

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