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 26, Problem 64P

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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Which D-aldopentose is oxidized to an optically active aldaric acid and undergoes the Wohl degradation to yield a D-aldotetrose that is oxidized to an optically active aldaric acid?

D-Aldopentose A is oxidized to an optically inactive aldaric acid. On Wohl degradation, A forms an aldotetrose B that is oxidized to an optically active aldaric acid. What are the structures of A and B?

Aldohexoses A and B are formed from aldopentose C via a Kiliani–Fischer synthesis. Nitric acid oxidizes A to an optically active aldaric acid, B to an optically inactive aldaric acid, and C to an optically active aldaric acid. Wohl degradation of C forms D, which is oxidized by nitric acid to an optically active aldaric acid. Wohl degradation of D forms (+)-glyceraldehyde. Identify A, B, C, and D.

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 26, Problem 64P

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 26, Problem 64P

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

Want to see the full answer?

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 26, Problem 64P

Interpretation Introduction