The reactions for Ruff degradation of D-arabinose and Kiliani Fischer synthesis of D-erythrose are to be shown and the structure of D-ribose is to be drawn. Concept introduction: Ruff degradation is a method which is used to shorten sugar chain. It is a two step process which starts with a bromine-water oxidation of the aldose to its aldonic acid. Then in the second step treatment of aldonic acid with hydrogen peroxide and ferric sulfate oxidizes the carbonyl group to CO 2 and give aldose with one fewer carbon atom. It is used primarily for the determination of structure and synthesis of new sugar. The Kiliani Fischer synthesis is a method of lengthening an aldose carbon chain by adding one carbon atom to the aldehyde end of the aldose. In Kiliani Fischer synthesis, the aldehyde carbon atom is made asymmetric with the formation of cyanohydrins in the first step. Then in the second step the hydrogenation of the following cyanohydrin gives two imines, which hydrolyzes to give aldehyde. Ruff degradation and Kiliani Fischer synthesis are the opposite methods of each other.

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Answer 1

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Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 23.11, Problem 23.32P

Interpretation Introduction

Interpretation:

The reactions for Ruff degradation of D-arabinose and Kiliani Fischer synthesis of D-erythrose are to be shown and the structure of D-ribose is to be drawn.

Concept introduction:

Ruff degradation is a method which is used to shorten sugar chain. It is a two step process which starts with a bromine-water oxidation of the aldose to its aldonic acid. Then in the second step treatment of aldonic acid with hydrogen peroxide and ferric sulfate oxidizes the carbonyl group to CO2 and give aldose with one fewer carbon atom. It is used primarily for the determination of structure and synthesis of new sugar.

The Kiliani Fischer synthesis is a method of lengthening an aldose carbon chain by adding one carbon atom to the aldehyde end of the aldose. In Kiliani Fischer synthesis, the aldehyde carbon atom is made asymmetric with the formation of cyanohydrins in the first step. Then in the second step the hydrogenation of the following cyanohydrin gives two imines, which hydrolyzes to give aldehyde.

Ruff degradation and Kiliani Fischer synthesis are the opposite methods of each other.

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Students have asked these similar questions

d-Xylose and d-lyxose are formed when d-threose undergoes a Kiliani–Fischer synthesis. d-Xylose is oxidized to an optically inactive aldaric acid,whereas d-lyxose forms an optically active aldaric acid. What are the structures of d-xylose and d-lyxose?

d-Altrose is an aldohexose. Ruff degradation of d-altrose gives the same aldopentose asdoes degradation of d-allose, the C3 epimer of glucose. Give the structure of d-altrose

An unknown β-d-aldohexose has only one axial substituent. A Wohl degradation forms a compound which, when treated with sodium borohydride, forms an optically active alditol. This information allows you to arrive at two possible structures for the β-d-aldohexose. What experiment can you carry out to distinguish between the two possibilities?

Answer 2

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Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 23.11, Problem 23.32P

Interpretation Introduction

Interpretation:

The reactions for Ruff degradation of D-arabinose and Kiliani Fischer synthesis of D-erythrose are to be shown and the structure of D-ribose is to be drawn.

Concept introduction:

Ruff degradation is a method which is used to shorten sugar chain. It is a two step process which starts with a bromine-water oxidation of the aldose to its aldonic acid. Then in the second step treatment of aldonic acid with hydrogen peroxide and ferric sulfate oxidizes the carbonyl group to CO2 and give aldose with one fewer carbon atom. It is used primarily for the determination of structure and synthesis of new sugar.

The Kiliani Fischer synthesis is a method of lengthening an aldose carbon chain by adding one carbon atom to the aldehyde end of the aldose. In Kiliani Fischer synthesis, the aldehyde carbon atom is made asymmetric with the formation of cyanohydrins in the first step. Then in the second step the hydrogenation of the following cyanohydrin gives two imines, which hydrolyzes to give aldehyde.

Ruff degradation and Kiliani Fischer synthesis are the opposite methods of each other.

Expert Solution & Answer

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Check out a sample textbook solution

See solution

Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 23.11, Problem 23.32P

Interpretation Introduction

Interpretation:

The reactions for Ruff degradation of D-arabinose and Kiliani Fischer synthesis of D-erythrose are to be shown and the structure of D-ribose is to be drawn.

Concept introduction:

Ruff degradation is a method which is used to shorten sugar chain. It is a two step process which starts with a bromine-water oxidation of the aldose to its aldonic acid. Then in the second step treatment of aldonic acid with hydrogen peroxide and ferric sulfate oxidizes the carbonyl group to CO2 and give aldose with one fewer carbon atom. It is used primarily for the determination of structure and synthesis of new sugar.

The Kiliani Fischer synthesis is a method of lengthening an aldose carbon chain by adding one carbon atom to the aldehyde end of the aldose. In Kiliani Fischer synthesis, the aldehyde carbon atom is made asymmetric with the formation of cyanohydrins in the first step. Then in the second step the hydrogenation of the following cyanohydrin gives two imines, which hydrolyzes to give aldehyde.

Ruff degradation and Kiliani Fischer synthesis are the opposite methods of each other.

Expert Solution & Answer

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Check out a sample textbook solution

See solution

Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 23.11, Problem 23.32P

Interpretation Introduction