Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 25.4, Problem 8P
Interpretation Introduction

a)

Interpretation:

Fischer projection of D-sugars are to be drawn.

Concept introduction:

Fischer Projections are typically used for depicting monosaccharides and amino acids. They are helpful with depicting monosaccharides, because they have so many stereocenters, and the different monosaccharides are all pretty similar, they are just different about the orientation of the stereocenters. The Fischer Projection allows us to quickly see the orientation of each monosaccharide.

Interpretation Introduction

b)

Interpretation:

Fischer projection of D-sugars are to be drawn.

Concept introduction:

Fischer Projections are typically used for depicting monosaccharides and amino acids. They are helpful with depicting monosaccharides, because they have so many stereocenters, and the different monosaccharides are all pretty similar, they are just different about the orientation of the stereocenters. The Fischer Projection allows us to quickly see the orientation of each monosaccharide.

Interpretation Introduction

c)

Interpretation:

Fischer projection of D-sugars are to be drawn.

Concept introduction:

Fischer Projections are typically used for depicting monosaccharides and amino acids. They are helpful with depicting monosaccharides, because they have so many stereocenters, and the different monosaccharides are all pretty similar, they are just different about the orientation of the stereocenters. The Fischer Projection allows us to quickly see the orientation of each monosaccharide.

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In 1891, Emil Fischer determined the structures of glucose and the seven other d-aldohexoses using only simple chemical reactions and clever reasoning about stereochemistry andsymmetry. He received the Nobel Prize for this work in 1902. Fischer had determined thatd-glucose is an aldohexose, and he used Ruff degradations to degrade it to (+)-glyceraldehyde. Therefore, the eight d-aldohexose structures shown in Figure 23-3 are the possiblestructures for glucose.Pretend that no names are shown in Figure 23-3 except for glyceraldehyde, and usethe following results to prove which of these structures represent glucose, mannose,arabinose, and erythrose.(a) Upon Ruff degradation, glucose and mannose give the same aldopentose: arabinose.Nitric acid oxidation of arabinose gives an optically active aldaric acid. What are thetwo possible structures of arabinose?(b) Upon Ruff degradation, arabinose gives the aldotetrose erythrose. Nitric acid oxidation of erythrose gives an optically inactive…
In 1891, Emil Fischer determined the structures of glucose and the seven other d-aldohexoses using only simple chemical reactions and clever reasoning about stereochemistry andsymmetry. He received the Nobel Prize for this work in 1902. Fischer had determined thatd-glucose is an aldohexose, and he used Ruff degradations to degrade it to (+)-glyceraldehyde. Therefore, the eight d-aldohexose structures shown in Figure 23-3 are the possiblestructures for glucose.Pretend that no names are shown in Figure 23-3 except for glyceraldehyde, and usethe following results to prove which of these structures represent glucose, mannose,arabinose, and erythrose.(a) Upon Ruff degradation, glucose and mannose give the same aldopentose: arabinose.Nitric acid oxidation of arabinose gives an optically active aldaric acid. What are thetwo possible structures of arabinose?(b) Upon Ruff degradation, arabinose gives the aldotetrose erythrose. Nitric acid oxidation of erythrose gives an optically inactive…
Show the steps in converting Fischer to Haworth to: Convert D-Talose to its aIpha pyranose structure. Convert D-Tagatose to its beta furanose structure.

Chapter 25 Solutions

Organic Chemistry

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