Fischer projections for two D-aldoheptoses whose stereochemistry at C 3 , C 4 , C 5 and C 6 is the same as that of D-glucose at C 2 , C 3 , C 4 and C 5 are to be drawn. Concept introduction: When a new chiral center is created in an optically active monosaccharide molecule the arrangement of H and OH on the new chiral center can be either H at left and OH at right or H at right and OH at left. Hence two isomers can be written. To draw: Fischer projections for two D-aldoheptoses whose stereochemistry at C 3 , C 4 , C 5 and C 6 is the same as that of D-glucose at C 2 , C 3 , C 4 and C 5 .

Question

Glucose is the most abundant monosaccharide. From memory, draw glucose in(a) the Fischer projection of the open chain.(b) the most stable chair conformation of the most stable pyranose anomer.(c) the Haworth projection of the most stable pyranose anomer

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.SE, Problem 43AP

Interpretation Introduction

Interpretation:

Fischer projections for two D-aldoheptoses whose stereochemistry at C₃, C₄, C₅ and C₆ is the same as that of D-glucose at C₂, C₃, C₄ and C₅ are to be drawn.

Concept introduction:

When a new chiral center is created in an optically active monosaccharide molecule the arrangement of H and OH on the new chiral center can be either H at left and OH at right or H at right and OH at left. Hence two isomers can be written.

To draw:

Fischer projections for two D-aldoheptoses whose stereochemistry at C₃, C₄, C₅ and C₆ is the same as that of D-glucose at C₂, C₃, C₄ and C₅.

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Glucose is the most abundant monosaccharide. From memory, draw glucose in(a) the Fischer projection of the open chain.(b) the most stable chair conformation of the most stable pyranose anomer.(c) the Haworth projection of the most stable pyranose anomer

Draw a chair conformation for the b-anomer of a disaccharide in which two units of d-glucopyranose are joined by an a-1,6-glycosidic bond.

The disaccharide lactose is built up by one D-galacto- and one D-gluco monosaccharide unit. Draw L-galactose in the Fischer projection (open) form and in its most stable pyranose ring conformation form and determine if the latter is a 1C4 or a 4C1 conformation.

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.SE, Problem 43AP

Interpretation Introduction

Interpretation:

Fischer projections for two D-aldoheptoses whose stereochemistry at C₃, C₄, C₅ and C₆ is the same as that of D-glucose at C₂, C₃, C₄ and C₅ are to be drawn.

Concept introduction:

When a new chiral center is created in an optically active monosaccharide molecule the arrangement of H and OH on the new chiral center can be either H at left and OH at right or H at right and OH at left. Hence two isomers can be written.

To draw:

Fischer projections for two D-aldoheptoses whose stereochemistry at C₃, C₄, C₅ and C₆ is the same as that of D-glucose at C₂, C₃, C₄ and C₅.

Expert Solution & Answer

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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.SE, Problem 43AP

Interpretation Introduction

Interpretation:

Fischer projections for two D-aldoheptoses whose stereochemistry at C₃, C₄, C₅ and C₆ is the same as that of D-glucose at C₂, C₃, C₄ and C₅ are to be drawn.

Concept introduction:

When a new chiral center is created in an optically active monosaccharide molecule the arrangement of H and OH on the new chiral center can be either H at left and OH at right or H at right and OH at left. Hence two isomers can be written.

To draw:

Fischer projections for two D-aldoheptoses whose stereochemistry at C₃, C₄, C₅ and C₆ is the same as that of D-glucose at C₂, C₃, C₄ and C₅.

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.SE, Problem 43AP

Interpretation Introduction