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

Ruff degradation of d-arabinose gives d-erythrose. The Kiliani–Fischer synthesis converts d-erythrose to a mixture of d-arabinose and d-ribose. Draw out these reactions, andgive the structure of d-ribose

Which aldopentose gives the same aldaric acid as D-xylose? Which aldopentose gives the same aldaric acid as D-arabinose?

An important technique for establishing relative configurations among isomeric aldoses and ketoses is to convert both terminal carbon atoms to the same functional group. This can be done either by selective oxidation or reduction. As a specific example, nitric acid oxidation of d-erythrose gives meso-tartaric acid . Similar oxidation of d-threose gives (2S,3S)-tartaric acid. Given this information and the fact that d-erythrose and d-threose are diastereomers, draw Fischer projections for d-erythrose and d-threose. Check your answers against Table 25.1.

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

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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