The D-aldopentose which on oxidation produces optically active aldaric acid and that undergoes Wohl Degradation to yield D-aldotetrose which on oxidation produces optically active aldaric acid is to be predicted. Concept introduction: Carbohydrates containing aldehydes are known as aldoses. Wohl Degradation is a method of shortening the aldose by one carbon atom by cleavage of C1 − C2 bond.

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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 28, Problem 28.61P

Interpretation Introduction

Interpretation: The D-aldopentose which on oxidation produces optically active aldaric acid and that undergoes Wohl Degradation to yield D-aldotetrose which on oxidation produces optically active aldaric acid is to be predicted.

Concept introduction: Carbohydrates containing aldehydes are known as aldoses. Wohl Degradation is a method of shortening the aldose by one carbon atom by cleavage of C1−C2 bond.

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Treatment with sodium borohydride converts aldose A to an optically inactive alditol. Wohl degradation of A forms B, whose alditol is optically inactive. Wohl degradation of B forms d-glyceraldehyde. Identify A and B.

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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?

Answer 2

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 28, Problem 28.61P

Interpretation Introduction

Interpretation: The D-aldopentose which on oxidation produces optically active aldaric acid and that undergoes Wohl Degradation to yield D-aldotetrose which on oxidation produces optically active aldaric acid is to be predicted.

Concept introduction: Carbohydrates containing aldehydes are known as aldoses. Wohl Degradation is a method of shortening the aldose by one carbon atom by cleavage of C1−C2 bond.

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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 28, Problem 28.61P

Interpretation Introduction

Interpretation: The D-aldopentose which on oxidation produces optically active aldaric acid and that undergoes Wohl Degradation to yield D-aldotetrose which on oxidation produces optically active aldaric acid is to be predicted.

Concept introduction: Carbohydrates containing aldehydes are known as aldoses. Wohl Degradation is a method of shortening the aldose by one carbon atom by cleavage of C1−C2 bond.

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 28, Problem 28.61P

Interpretation Introduction