The aldose compounds that would yield phenylosazone similar to L-sorbose are to be identified. Concept Introduction: ▸ Monosaccharide L − sorbose is a ketose, which is often used as the starting material for commercial production of vitamin C ( L − ascorbic acid ). ▸ Compounds formed by the reaction of reducing sugars with excess of phenylhydrazine are called osazones . These are highly crystalline and colored compounds and are formed by the reducing sugar molecules.

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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 22, Problem 25P

Interpretation Introduction

Interpretation:

The aldose compounds that would yield phenylosazone similar to L-sorbose are to be identified.

Concept Introduction:

▸ Monosaccharide L−sorbose is a ketose, which is often used as the starting material for commercial production of vitamin C (L−ascorbic acid).

▸ Compounds formed by the reaction of reducing sugars with excess of phenylhydrazine are called osazones. These are highly crystalline and colored compounds and are formed by the reducing sugar molecules.

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(a) Which of the d-aldopentoses will give optically active aldaric acids on oxidation with HNO3 ?(b) Which of the d-aldotetroses will give optically active aldaric acids on oxidation with HNO3 ?(c) Sugar X is known to be a d-aldohexose. On oxidation with HNO3, X gives an optically inactive aldaric acid. WhenX is degraded to an aldopentose, oxidation of the aldopentose gives an optically active aldaric acid. Determine thestructure of X.(d) Even though sugar X gives an optically inactive aldaric acid, the pentose formed by degradation gives an opticallyactive aldaric acid. Does this finding contradict the principle that optically inactive reagents cannot form opticallyactive products?(e) Show what product results if the aldopentose formed from degradation of X is further degraded to an aldotetrose.Does HNO3 oxidize this aldotetrose to an optically active aldaric acid?

A D-aldopentose A is oxidized to an optically inactive aldaric acid with HNO3. A is formed by the Kiliani–Fischer synthesis of a D-aldotetrose B, which is also oxidized to an optically inactive aldaric acid with HNO3. What are the structures of A and B?

Compound A is a D-aldopentose that can be oxidized to an optically inactive aldaric acid B. On Kiliani-Fischer chain extension, A is converted into C and D; C can be oxidized to an optically active aldaric acid E, but D is oxidized to an optically inactive aldaric acid F. What is the structure of compound F? • Use the wedge/hash bond tools to indicate stereochemistry where it exists. You do not have to explicitly draw H atoms. If a group is achiral, do not use wedged or hashed bonds on it. • Show stereochemistry in a meso compound. • Do not include lone pairs in your answer. They will not be considered in the grading.

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 22, Problem 25P

Interpretation Introduction

Interpretation:

The aldose compounds that would yield phenylosazone similar to L-sorbose are to be identified.

Concept Introduction:

▸ Monosaccharide L−sorbose is a ketose, which is often used as the starting material for commercial production of vitamin C (L−ascorbic acid).

▸ Compounds formed by the reaction of reducing sugars with excess of phenylhydrazine are called osazones. These are highly crystalline and colored compounds and are formed by the reducing sugar molecules.

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Answer 3

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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 22, Problem 25P

Interpretation Introduction

Interpretation:

The aldose compounds that would yield phenylosazone similar to L-sorbose are to be identified.

Concept Introduction:

▸ Monosaccharide L−sorbose is a ketose, which is often used as the starting material for commercial production of vitamin C (L−ascorbic acid).

▸ Compounds formed by the reaction of reducing sugars with excess of phenylhydrazine are called osazones. These are highly crystalline and colored compounds and are formed by the reducing sugar molecules.

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 22, Problem 25P

Interpretation Introduction