D-Allose and D-glucose are stereoisomers. In the open chain form, hexose sugars have four chiral centres. Glucose and allose differ in the stereochemistry only at carbon three and are hence called C3 epimers. Concept introduction: When D-glucose is treated with nitric acid, oxidation of D-glucose takes place. The aldehyde and alcohol group of glucose are oxidized to carboxylic acids forming D-glucaric acid and similarly Allose oxidised to D-Allose acid on treatment with dilute nitric acid.

Question

Treatment of D-glucose with NaBH4 gives an alditol A. What L-aldohexose also yields A when treated with NaBH4?

Answer 1

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 25.6, Problem 19P

Interpretation Introduction

Interpretation:

D-Allose and D-glucose are stereoisomers. In the open chain form, hexose sugars have four chiral centres. Glucose and allose differ in the stereochemistry only at carbon three and are hence called C3 epimers.

Concept introduction:

When D-glucose is treated with nitric acid, oxidation of D-glucose takes place. The aldehyde and alcohol group of glucose are oxidized to carboxylic acids forming D-glucaric acid and similarly Allose oxidised to D-Allose acid on treatment with dilute nitric acid.

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Treatment of D-glucose with NaBH4 gives an alditol A. What L-aldohexose also yields A when treated with NaBH4?

A D-aldohexose A is formed from an aldopentose B by the Kiliani–Fischer synthesis. Reduction of A with NaBH4 forms an optically inactive alditol. Oxidation of B forms an optically active aldaric acid. What are the structures of A and B?

An oligosaccharide isolated from an organism is found tocontain two glucose residues and one galactose residue.Exhaustive methylation followed by hydrolysis producedtwo glucoses with methoxy groups at positions 2, 3,and 6 and galactose with methoxy groups at positions2, 3, 4, and 6. What is the structure of the originaloligosaccharide?

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 25.6, Problem 19P

Interpretation Introduction

Interpretation:

D-Allose and D-glucose are stereoisomers. In the open chain form, hexose sugars have four chiral centres. Glucose and allose differ in the stereochemistry only at carbon three and are hence called C3 epimers.

Concept introduction:

When D-glucose is treated with nitric acid, oxidation of D-glucose takes place. The aldehyde and alcohol group of glucose are oxidized to carboxylic acids forming D-glucaric acid and similarly Allose oxidised to D-Allose acid on treatment with dilute nitric acid.

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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 25.6, Problem 19P

Interpretation Introduction

Interpretation:

D-Allose and D-glucose are stereoisomers. In the open chain form, hexose sugars have four chiral centres. Glucose and allose differ in the stereochemistry only at carbon three and are hence called C3 epimers.

Concept introduction:

When D-glucose is treated with nitric acid, oxidation of D-glucose takes place. The aldehyde and alcohol group of glucose are oxidized to carboxylic acids forming D-glucaric acid and similarly Allose oxidised to D-Allose acid on treatment with dilute nitric acid.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook 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 25.6, Problem 19P

Interpretation Introduction