(a) Interpretation: Whether α − D − glucopyranose and β − D − glucopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated. Concept introduction: Sugars show different types of isomerism. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Question

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Answer 1

Question

Chapter 24, Problem 24.39AP

Interpretation Introduction

(a)

Interpretation:

Whether α−D−glucopyranose and β−D−glucopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, α−D−glucopyranose and β−D−glucopyranose are anomers as well as diastereomers of each other.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 1

Explanation of Solution

The compounds, α−D−glucopyranose and β−D−glucopyranose are anomers because their stereochemistry is different at anomeric carbon. Anomeric carbon is carbon −1 in aldose or carbon −2 in ketose.

They are diastereomers also as they are not mirror images of each other. The structure of both the compounds is shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 2

Figure 1

Conclusion

These two compounds are anomers as well as diastereomers as shown in Figure 1.

Interpretation Introduction

(b)

Interpretation:

Whether α−D−glucopyranose and α−D−mannopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, α−D−glucopyranose and α−D−mannopyranose are epimers as well as diastereomers of each other.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 3

Explanation of Solution

Both the above structures of α−D−glucopyranose and α−D−mannopyranose are diastereomers as they are not mirror images. They are epimers as they differ in stereochemistry at carbon −2, −H and −OH bonds are present on different sides of carbon atom as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 4

Figure 2

Conclusion

The compounds α−D−glucopyranose and α−D−mannopyranose are epimers and diastereomers as shown in Figure 2.

Interpretation Introduction

(c)

Interpretation:

Whether β−D−mannopyranose and β−L−mannopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, β−D−mannopyranose and β−L−mannopyranose are enantiomers as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 5

Explanation of Solution

Sugars can be divided into two groups based on the symmetry of carbon atoms. If the molecule has asymmetric carbon atom it will have a non superimposable mirror image. The non superimposable mirror images are known as enantiomers. As the given compounds are non super imposable mirror images of each other they are enantiomers. This can be well explained by the illustrations shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 6

Figure 3

Conclusion

These two compounds β−D−mannopyranose and β−L−mannopyranose are enantiomers of each other as shown in Figure 3.

Interpretation Introduction

(d)

Interpretation:

Whether α−D−ribofuranose and α−D−ribopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, α−D−ribofuranose and α−D−ribopyranose are constitutional isomers as they have same molecular formula but different chemical structure as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 7

Explanation of Solution

As the isomers are the compounds, having similar chemical formula but different structures. These two compounds have same chemical formula. The chemical structure is of these two compounds is quite different as shown in Figure 4.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 8

Figure 4

In the above shown compounds, one is a pentose sugar furanose while the other is a hexose sugar pyranose.

Conclusion

These two compounds, α−D−ribofuranose and α−D−ribopyranose are constitutional isomers as shown in Figure 4.

Interpretation Introduction

(e)

Interpretation:

Whether D−Glucose and α−D−glucopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

Aldehyde form of D−Glucose and α−D−glucopyranose are constitutional isomers. Their chemical structure is different but molecular formula is same as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 9

Explanation of Solution

As the isomers are the compounds, having similar chemical formula but different structures. Both the above structures are constitutional isomers as shown below in the Figure.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 10

Figure 5

In the above shown compounds, one is a ring structure having keto group while the other is open ring structure having aldehyde as the functional group. The chemical formula of the given compounds is same but their properties are totally different.

Conclusion

The given compounds D−Glucose and α−D−glucopyranose are different in chemical structure and therefore their properties are different. So, they are constitutional isomers as shown in Figure 5.

Interpretation Introduction

(f)

Interpretation:

Whether the compounds, methyl α−D−fructofuranoside and 2−O−methyl−α−D−fructofuranose are enantiomers. epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons. The naming of the same compound can be done in different manners.

Expert Solution

Answer to Problem 24.39AP

The compounds, methyl α−D−fructofuranoside and 2−O−methyl−α−D−fructofuranose are identical compounds only the way of naming is different.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 11

Explanation of Solution

The structure of methyl α−D−fructofuranoside or 2−O−methyl−α−D−fructofuranose is shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 12

Figure 6

So, the compound is same, they are identical. In first name it is taken as methyl derivative of α−D−fructofuranoside as in second name methyl is taken on carbon attached to oxygen atom which is again the α carbon on atom. They are identical compounds not isomers.

Conclusion

The compound shown in Figure 6 can be named as methyl α−D−fructofuranoside as well as 2−O−methyl−α−D−fructofuranose. Both are the name of the same structure.

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Answer 2

Question

Chapter 24, Problem 24.39AP

Interpretation Introduction

(a)

Interpretation:

Whether α−D−glucopyranose and β−D−glucopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, α−D−glucopyranose and β−D−glucopyranose are anomers as well as diastereomers of each other.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 1

Explanation of Solution

The compounds, α−D−glucopyranose and β−D−glucopyranose are anomers because their stereochemistry is different at anomeric carbon. Anomeric carbon is carbon −1 in aldose or carbon −2 in ketose.

They are diastereomers also as they are not mirror images of each other. The structure of both the compounds is shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 2

Figure 1

Conclusion

These two compounds are anomers as well as diastereomers as shown in Figure 1.

Interpretation Introduction

(b)

Interpretation:

Whether α−D−glucopyranose and α−D−mannopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, α−D−glucopyranose and α−D−mannopyranose are epimers as well as diastereomers of each other.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 3

Explanation of Solution

Both the above structures of α−D−glucopyranose and α−D−mannopyranose are diastereomers as they are not mirror images. They are epimers as they differ in stereochemistry at carbon −2, −H and −OH bonds are present on different sides of carbon atom as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 4

Figure 2

Conclusion

The compounds α−D−glucopyranose and α−D−mannopyranose are epimers and diastereomers as shown in Figure 2.

Interpretation Introduction

(c)

Interpretation:

Whether β−D−mannopyranose and β−L−mannopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, β−D−mannopyranose and β−L−mannopyranose are enantiomers as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 5

Explanation of Solution

Sugars can be divided into two groups based on the symmetry of carbon atoms. If the molecule has asymmetric carbon atom it will have a non superimposable mirror image. The non superimposable mirror images are known as enantiomers. As the given compounds are non super imposable mirror images of each other they are enantiomers. This can be well explained by the illustrations shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 6

Figure 3

Conclusion

These two compounds β−D−mannopyranose and β−L−mannopyranose are enantiomers of each other as shown in Figure 3.

Interpretation Introduction

(d)

Interpretation:

Whether α−D−ribofuranose and α−D−ribopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, α−D−ribofuranose and α−D−ribopyranose are constitutional isomers as they have same molecular formula but different chemical structure as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 7

Explanation of Solution

As the isomers are the compounds, having similar chemical formula but different structures. These two compounds have same chemical formula. The chemical structure is of these two compounds is quite different as shown in Figure 4.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 8

Figure 4

In the above shown compounds, one is a pentose sugar furanose while the other is a hexose sugar pyranose.

Conclusion

These two compounds, α−D−ribofuranose and α−D−ribopyranose are constitutional isomers as shown in Figure 4.

Interpretation Introduction

(e)

Interpretation:

Whether D−Glucose and α−D−glucopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

Aldehyde form of D−Glucose and α−D−glucopyranose are constitutional isomers. Their chemical structure is different but molecular formula is same as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 9

Explanation of Solution

As the isomers are the compounds, having similar chemical formula but different structures. Both the above structures are constitutional isomers as shown below in the Figure.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 10

Figure 5

In the above shown compounds, one is a ring structure having keto group while the other is open ring structure having aldehyde as the functional group. The chemical formula of the given compounds is same but their properties are totally different.

Conclusion

The given compounds D−Glucose and α−D−glucopyranose are different in chemical structure and therefore their properties are different. So, they are constitutional isomers as shown in Figure 5.

Interpretation Introduction

(f)

Interpretation:

Whether the compounds, methyl α−D−fructofuranoside and 2−O−methyl−α−D−fructofuranose are enantiomers. epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons. The naming of the same compound can be done in different manners.

Expert Solution

Answer to Problem 24.39AP

The compounds, methyl α−D−fructofuranoside and 2−O−methyl−α−D−fructofuranose are identical compounds only the way of naming is different.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 11

Explanation of Solution

The structure of methyl α−D−fructofuranoside or 2−O−methyl−α−D−fructofuranose is shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 12

Figure 6

So, the compound is same, they are identical. In first name it is taken as methyl derivative of α−D−fructofuranoside as in second name methyl is taken on carbon attached to oxygen atom which is again the α carbon on atom. They are identical compounds not isomers.

Conclusion

The compound shown in Figure 6 can be named as methyl α−D−fructofuranoside as well as 2−O−methyl−α−D−fructofuranose. Both are the name of the same structure.

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Answer 3

Question

Chapter 24, Problem 24.39AP

Interpretation Introduction

(a)

Interpretation:

Whether α−D−glucopyranose and β−D−glucopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, α−D−glucopyranose and β−D−glucopyranose are anomers as well as diastereomers of each other.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 1

Explanation of Solution

The compounds, α−D−glucopyranose and β−D−glucopyranose are anomers because their stereochemistry is different at anomeric carbon. Anomeric carbon is carbon −1 in aldose or carbon −2 in ketose.

They are diastereomers also as they are not mirror images of each other. The structure of both the compounds is shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 2

Figure 1

Conclusion

These two compounds are anomers as well as diastereomers as shown in Figure 1.

Interpretation Introduction

(b)

Interpretation:

Whether α−D−glucopyranose and α−D−mannopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, α−D−glucopyranose and α−D−mannopyranose are epimers as well as diastereomers of each other.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 3

Explanation of Solution

Both the above structures of α−D−glucopyranose and α−D−mannopyranose are diastereomers as they are not mirror images. They are epimers as they differ in stereochemistry at carbon −2, −H and −OH bonds are present on different sides of carbon atom as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 4

Figure 2

Conclusion

The compounds α−D−glucopyranose and α−D−mannopyranose are epimers and diastereomers as shown in Figure 2.

Interpretation Introduction

(c)

Interpretation:

Whether β−D−mannopyranose and β−L−mannopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, β−D−mannopyranose and β−L−mannopyranose are enantiomers as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 5

Explanation of Solution

Sugars can be divided into two groups based on the symmetry of carbon atoms. If the molecule has asymmetric carbon atom it will have a non superimposable mirror image. The non superimposable mirror images are known as enantiomers. As the given compounds are non super imposable mirror images of each other they are enantiomers. This can be well explained by the illustrations shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 6

Figure 3

Conclusion

These two compounds β−D−mannopyranose and β−L−mannopyranose are enantiomers of each other as shown in Figure 3.

Interpretation Introduction

(d)

Interpretation:

Whether α−D−ribofuranose and α−D−ribopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, α−D−ribofuranose and α−D−ribopyranose are constitutional isomers as they have same molecular formula but different chemical structure as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 7

Explanation of Solution

As the isomers are the compounds, having similar chemical formula but different structures. These two compounds have same chemical formula. The chemical structure is of these two compounds is quite different as shown in Figure 4.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 8

Figure 4

In the above shown compounds, one is a pentose sugar furanose while the other is a hexose sugar pyranose.

Conclusion

These two compounds, α−D−ribofuranose and α−D−ribopyranose are constitutional isomers as shown in Figure 4.

Interpretation Introduction

(e)

Interpretation:

Whether D−Glucose and α−D−glucopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

Aldehyde form of D−Glucose and α−D−glucopyranose are constitutional isomers. Their chemical structure is different but molecular formula is same as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 9

Explanation of Solution

As the isomers are the compounds, having similar chemical formula but different structures. Both the above structures are constitutional isomers as shown below in the Figure.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 10

Figure 5

In the above shown compounds, one is a ring structure having keto group while the other is open ring structure having aldehyde as the functional group. The chemical formula of the given compounds is same but their properties are totally different.

Conclusion

The given compounds D−Glucose and α−D−glucopyranose are different in chemical structure and therefore their properties are different. So, they are constitutional isomers as shown in Figure 5.

Interpretation Introduction

(f)

Interpretation:

Whether the compounds, methyl α−D−fructofuranoside and 2−O−methyl−α−D−fructofuranose are enantiomers. epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons. The naming of the same compound can be done in different manners.

Expert Solution

Answer to Problem 24.39AP

The compounds, methyl α−D−fructofuranoside and 2−O−methyl−α−D−fructofuranose are identical compounds only the way of naming is different.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 11

Explanation of Solution

The structure of methyl α−D−fructofuranoside or 2−O−methyl−α−D−fructofuranose is shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 12

Figure 6

So, the compound is same, they are identical. In first name it is taken as methyl derivative of α−D−fructofuranoside as in second name methyl is taken on carbon attached to oxygen atom which is again the α carbon on atom. They are identical compounds not isomers.

Conclusion

The compound shown in Figure 6 can be named as methyl α−D−fructofuranoside as well as 2−O−methyl−α−D−fructofuranose. Both are the name of the same structure.

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Answer 4

Question

Chapter 24, Problem 24.39AP

Interpretation Introduction

(a)

Interpretation:

Whether α−D−glucopyranose and β−D−glucopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, α−D−glucopyranose and β−D−glucopyranose are anomers as well as diastereomers of each other.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 1

Explanation of Solution

The compounds, α−D−glucopyranose and β−D−glucopyranose are anomers because their stereochemistry is different at anomeric carbon. Anomeric carbon is carbon −1 in aldose or carbon −2 in ketose.

They are diastereomers also as they are not mirror images of each other. The structure of both the compounds is shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 2

Figure 1

Conclusion

These two compounds are anomers as well as diastereomers as shown in Figure 1.

Interpretation Introduction

(b)

Interpretation:

Whether α−D−glucopyranose and α−D−mannopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, α−D−glucopyranose and α−D−mannopyranose are epimers as well as diastereomers of each other.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 3

Explanation of Solution

Both the above structures of α−D−glucopyranose and α−D−mannopyranose are diastereomers as they are not mirror images. They are epimers as they differ in stereochemistry at carbon −2, −H and −OH bonds are present on different sides of carbon atom as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 4

Figure 2

Conclusion

The compounds α−D−glucopyranose and α−D−mannopyranose are epimers and diastereomers as shown in Figure 2.

Interpretation Introduction

(c)

Interpretation:

Whether β−D−mannopyranose and β−L−mannopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, β−D−mannopyranose and β−L−mannopyranose are enantiomers as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 5

Explanation of Solution

Sugars can be divided into two groups based on the symmetry of carbon atoms. If the molecule has asymmetric carbon atom it will have a non superimposable mirror image. The non superimposable mirror images are known as enantiomers. As the given compounds are non super imposable mirror images of each other they are enantiomers. This can be well explained by the illustrations shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 6

Figure 3

Conclusion

These two compounds β−D−mannopyranose and β−L−mannopyranose are enantiomers of each other as shown in Figure 3.

Interpretation Introduction

(d)

Interpretation:

Whether α−D−ribofuranose and α−D−ribopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, α−D−ribofuranose and α−D−ribopyranose are constitutional isomers as they have same molecular formula but different chemical structure as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 7

Explanation of Solution

As the isomers are the compounds, having similar chemical formula but different structures. These two compounds have same chemical formula. The chemical structure is of these two compounds is quite different as shown in Figure 4.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 8

Figure 4

In the above shown compounds, one is a pentose sugar furanose while the other is a hexose sugar pyranose.

Conclusion

These two compounds, α−D−ribofuranose and α−D−ribopyranose are constitutional isomers as shown in Figure 4.

Interpretation Introduction

(e)

Interpretation:

Whether D−Glucose and α−D−glucopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

Aldehyde form of D−Glucose and α−D−glucopyranose are constitutional isomers. Their chemical structure is different but molecular formula is same as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 9

Explanation of Solution

As the isomers are the compounds, having similar chemical formula but different structures. Both the above structures are constitutional isomers as shown below in the Figure.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 10

Figure 5

In the above shown compounds, one is a ring structure having keto group while the other is open ring structure having aldehyde as the functional group. The chemical formula of the given compounds is same but their properties are totally different.

Conclusion

The given compounds D−Glucose and α−D−glucopyranose are different in chemical structure and therefore their properties are different. So, they are constitutional isomers as shown in Figure 5.

Interpretation Introduction

(f)

Interpretation:

Whether the compounds, methyl α−D−fructofuranoside and 2−O−methyl−α−D−fructofuranose are enantiomers. epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons. The naming of the same compound can be done in different manners.

Expert Solution

Answer to Problem 24.39AP

The compounds, methyl α−D−fructofuranoside and 2−O−methyl−α−D−fructofuranose are identical compounds only the way of naming is different.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 11

Explanation of Solution

The structure of methyl α−D−fructofuranoside or 2−O−methyl−α−D−fructofuranose is shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 12

Figure 6

So, the compound is same, they are identical. In first name it is taken as methyl derivative of α−D−fructofuranoside as in second name methyl is taken on carbon attached to oxygen atom which is again the α carbon on atom. They are identical compounds not isomers.

Conclusion

The compound shown in Figure 6 can be named as methyl α−D−fructofuranoside as well as 2−O−methyl−α−D−fructofuranose. Both are the name of the same structure.

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Answer 5

Chapter 24, Problem 24.39AP

Interpretation Introduction

(a)

Interpretation:

Whether α−D−glucopyranose and β−D−glucopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, α−D−glucopyranose and β−D−glucopyranose are anomers as well as diastereomers of each other.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 1

Explanation of Solution

The compounds, α−D−glucopyranose and β−D−glucopyranose are anomers because their stereochemistry is different at anomeric carbon. Anomeric carbon is carbon −1 in aldose or carbon −2 in ketose.

They are diastereomers also as they are not mirror images of each other. The structure of both the compounds is shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 2

Figure 1

Conclusion

These two compounds are anomers as well as diastereomers as shown in Figure 1.

Interpretation Introduction

(b)

Interpretation:

Whether α−D−glucopyranose and α−D−mannopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, α−D−glucopyranose and α−D−mannopyranose are epimers as well as diastereomers of each other.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 3

Explanation of Solution

Both the above structures of α−D−glucopyranose and α−D−mannopyranose are diastereomers as they are not mirror images. They are epimers as they differ in stereochemistry at carbon −2, −H and −OH bonds are present on different sides of carbon atom as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 4

Figure 2

Conclusion

The compounds α−D−glucopyranose and α−D−mannopyranose are epimers and diastereomers as shown in Figure 2.

Interpretation Introduction

(c)

Interpretation:

Whether β−D−mannopyranose and β−L−mannopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, β−D−mannopyranose and β−L−mannopyranose are enantiomers as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 5

Explanation of Solution

Sugars can be divided into two groups based on the symmetry of carbon atoms. If the molecule has asymmetric carbon atom it will have a non superimposable mirror image. The non superimposable mirror images are known as enantiomers. As the given compounds are non super imposable mirror images of each other they are enantiomers. This can be well explained by the illustrations shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 6

Figure 3

Conclusion

These two compounds β−D−mannopyranose and β−L−mannopyranose are enantiomers of each other as shown in Figure 3.

Interpretation Introduction

(d)

Interpretation:

Whether α−D−ribofuranose and α−D−ribopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, α−D−ribofuranose and α−D−ribopyranose are constitutional isomers as they have same molecular formula but different chemical structure as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 7

Explanation of Solution

As the isomers are the compounds, having similar chemical formula but different structures. These two compounds have same chemical formula. The chemical structure is of these two compounds is quite different as shown in Figure 4.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 8

Figure 4

In the above shown compounds, one is a pentose sugar furanose while the other is a hexose sugar pyranose.

Conclusion

These two compounds, α−D−ribofuranose and α−D−ribopyranose are constitutional isomers as shown in Figure 4.

Interpretation Introduction

(e)

Interpretation:

Whether D−Glucose and α−D−glucopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

Aldehyde form of D−Glucose and α−D−glucopyranose are constitutional isomers. Their chemical structure is different but molecular formula is same as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 9

Explanation of Solution

As the isomers are the compounds, having similar chemical formula but different structures. Both the above structures are constitutional isomers as shown below in the Figure.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 10

Figure 5

In the above shown compounds, one is a ring structure having keto group while the other is open ring structure having aldehyde as the functional group. The chemical formula of the given compounds is same but their properties are totally different.

Conclusion

The given compounds D−Glucose and α−D−glucopyranose are different in chemical structure and therefore their properties are different. So, they are constitutional isomers as shown in Figure 5.

Interpretation Introduction

(f)

Interpretation:

Whether the compounds, methyl α−D−fructofuranoside and 2−O−methyl−α−D−fructofuranose are enantiomers. epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons. The naming of the same compound can be done in different manners.

Expert Solution

Answer to Problem 24.39AP

The compounds, methyl α−D−fructofuranoside and 2−O−methyl−α−D−fructofuranose are identical compounds only the way of naming is different.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 11

Explanation of Solution

The structure of methyl α−D−fructofuranoside or 2−O−methyl−α−D−fructofuranose is shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 12

Figure 6

So, the compound is same, they are identical. In first name it is taken as methyl derivative of α−D−fructofuranoside as in second name methyl is taken on carbon attached to oxygen atom which is again the α carbon on atom. They are identical compounds not isomers.

Conclusion

The compound shown in Figure 6 can be named as methyl α−D−fructofuranoside as well as 2−O−methyl−α−D−fructofuranose. Both are the name of the same structure.

Answer 6

Chapter 24, Problem 24.39AP

Interpretation Introduction

(a)

Interpretation:

Whether α−D−glucopyranose and β−D−glucopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, α−D−glucopyranose and β−D−glucopyranose are anomers as well as diastereomers of each other.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 1

Explanation of Solution

The compounds, α−D−glucopyranose and β−D−glucopyranose are anomers because their stereochemistry is different at anomeric carbon. Anomeric carbon is carbon −1 in aldose or carbon −2 in ketose.

They are diastereomers also as they are not mirror images of each other. The structure of both the compounds is shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 2

Figure 1

Conclusion

These two compounds are anomers as well as diastereomers as shown in Figure 1.

Answer 7

Chapter 24, Problem 24.39AP

Interpretation Introduction

(a)

Interpretation:

Whether α−D−glucopyranose and β−D−glucopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Answer 8

Expert Solution

Answer to Problem 24.39AP

The compounds, α−D−glucopyranose and β−D−glucopyranose are anomers as well as diastereomers of each other.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 1

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

The compounds, α−D−glucopyranose and β−D−glucopyranose are anomers because their stereochemistry is different at anomeric carbon. Anomeric carbon is carbon −1 in aldose or carbon −2 in ketose.

They are diastereomers also as they are not mirror images of each other. The structure of both the compounds is shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 2

Figure 1

Answer 13

Conclusion

These two compounds are anomers as well as diastereomers as shown in Figure 1.

Answer 14

Interpretation Introduction

(b)

Interpretation:

Whether α−D−glucopyranose and α−D−mannopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, α−D−glucopyranose and α−D−mannopyranose are epimers as well as diastereomers of each other.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 3

Explanation of Solution

Both the above structures of α−D−glucopyranose and α−D−mannopyranose are diastereomers as they are not mirror images. They are epimers as they differ in stereochemistry at carbon −2, −H and −OH bonds are present on different sides of carbon atom as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 4

Figure 2

Conclusion

The compounds α−D−glucopyranose and α−D−mannopyranose are epimers and diastereomers as shown in Figure 2.

Answer 15

Interpretation Introduction

(b)

Interpretation:

Whether α−D−glucopyranose and α−D−mannopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Answer 16

Expert Solution

Answer to Problem 24.39AP

The compounds, α−D−glucopyranose and α−D−mannopyranose are epimers as well as diastereomers of each other.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 3

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

Both the above structures of α−D−glucopyranose and α−D−mannopyranose are diastereomers as they are not mirror images. They are epimers as they differ in stereochemistry at carbon −2, −H and −OH bonds are present on different sides of carbon atom as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 4

Figure 2

Answer 21

Conclusion

The compounds α−D−glucopyranose and α−D−mannopyranose are epimers and diastereomers as shown in Figure 2.

Answer 22

Interpretation Introduction

(c)

Interpretation:

Whether β−D−mannopyranose and β−L−mannopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, β−D−mannopyranose and β−L−mannopyranose are enantiomers as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 5

Explanation of Solution

Sugars can be divided into two groups based on the symmetry of carbon atoms. If the molecule has asymmetric carbon atom it will have a non superimposable mirror image. The non superimposable mirror images are known as enantiomers. As the given compounds are non super imposable mirror images of each other they are enantiomers. This can be well explained by the illustrations shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 6

Figure 3

Conclusion

These two compounds β−D−mannopyranose and β−L−mannopyranose are enantiomers of each other as shown in Figure 3.

Answer 23

Interpretation Introduction

(c)

Interpretation:

Whether β−D−mannopyranose and β−L−mannopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Answer 24

Expert Solution

Answer to Problem 24.39AP

The compounds, β−D−mannopyranose and β−L−mannopyranose are enantiomers as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 5

Answer 25

Expert Solution

Answer 26

Expert Solution

Answer 27

Expert Solution

Answer 28

Explanation of Solution

Sugars can be divided into two groups based on the symmetry of carbon atoms. If the molecule has asymmetric carbon atom it will have a non superimposable mirror image. The non superimposable mirror images are known as enantiomers. As the given compounds are non super imposable mirror images of each other they are enantiomers. This can be well explained by the illustrations shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 6

Figure 3

Answer 29

Conclusion

These two compounds β−D−mannopyranose and β−L−mannopyranose are enantiomers of each other as shown in Figure 3.

Answer 30

Interpretation Introduction

(d)

Interpretation:

Whether α−D−ribofuranose and α−D−ribopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

The compounds, α−D−ribofuranose and α−D−ribopyranose are constitutional isomers as they have same molecular formula but different chemical structure as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 7

Explanation of Solution

As the isomers are the compounds, having similar chemical formula but different structures. These two compounds have same chemical formula. The chemical structure is of these two compounds is quite different as shown in Figure 4.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 8

Figure 4

In the above shown compounds, one is a pentose sugar furanose while the other is a hexose sugar pyranose.

Conclusion

These two compounds, α−D−ribofuranose and α−D−ribopyranose are constitutional isomers as shown in Figure 4.

Answer 31

Interpretation Introduction

(d)

Interpretation:

Whether α−D−ribofuranose and α−D−ribopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Answer 32

Expert Solution

Answer to Problem 24.39AP

The compounds, α−D−ribofuranose and α−D−ribopyranose are constitutional isomers as they have same molecular formula but different chemical structure as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 7

Answer 33

Expert Solution

Answer 34

Expert Solution

Answer 35

Expert Solution

Answer 36

Explanation of Solution

As the isomers are the compounds, having similar chemical formula but different structures. These two compounds have same chemical formula. The chemical structure is of these two compounds is quite different as shown in Figure 4.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 8

Figure 4

In the above shown compounds, one is a pentose sugar furanose while the other is a hexose sugar pyranose.

Answer 37

Conclusion

These two compounds, α−D−ribofuranose and α−D−ribopyranose are constitutional isomers as shown in Figure 4.

Answer 38

Interpretation Introduction

(e)

Interpretation:

Whether D−Glucose and α−D−glucopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Expert Solution

Answer to Problem 24.39AP

Aldehyde form of D−Glucose and α−D−glucopyranose are constitutional isomers. Their chemical structure is different but molecular formula is same as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 9

Explanation of Solution

As the isomers are the compounds, having similar chemical formula but different structures. Both the above structures are constitutional isomers as shown below in the Figure.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 10

Figure 5

In the above shown compounds, one is a ring structure having keto group while the other is open ring structure having aldehyde as the functional group. The chemical formula of the given compounds is same but their properties are totally different.

Conclusion

The given compounds D−Glucose and α−D−glucopyranose are different in chemical structure and therefore their properties are different. So, they are constitutional isomers as shown in Figure 5.

Answer 39

Interpretation Introduction

(e)

Interpretation:

Whether D−Glucose and α−D−glucopyranose are epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated.

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons.

Answer 40

Expert Solution

Answer to Problem 24.39AP

Aldehyde form of D−Glucose and α−D−glucopyranose are constitutional isomers. Their chemical structure is different but molecular formula is same as shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 9

Answer 41

Expert Solution

Answer 42

Expert Solution

Answer 43

Expert Solution

Answer 44

Explanation of Solution

As the isomers are the compounds, having similar chemical formula but different structures. Both the above structures are constitutional isomers as shown below in the Figure.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 10

Figure 5

In the above shown compounds, one is a ring structure having keto group while the other is open ring structure having aldehyde as the functional group. The chemical formula of the given compounds is same but their properties are totally different.

Answer 45

Conclusion

The given compounds D−Glucose and α−D−glucopyranose are different in chemical structure and therefore their properties are different. So, they are constitutional isomers as shown in Figure 5.

Answer 46

Interpretation Introduction

(f)

Interpretation:

Whether the compounds, methyl α−D−fructofuranoside and 2−O−methyl−α−D−fructofuranose are enantiomers. epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons. The naming of the same compound can be done in different manners.

Expert Solution

Answer to Problem 24.39AP

The compounds, methyl α−D−fructofuranoside and 2−O−methyl−α−D−fructofuranose are identical compounds only the way of naming is different.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 11

Explanation of Solution

The structure of methyl α−D−fructofuranoside or 2−O−methyl−α−D−fructofuranose is shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 12

Figure 6

So, the compound is same, they are identical. In first name it is taken as methyl derivative of α−D−fructofuranoside as in second name methyl is taken on carbon attached to oxygen atom which is again the α carbon on atom. They are identical compounds not isomers.

Conclusion

The compound shown in Figure 6 can be named as methyl α−D−fructofuranoside as well as 2−O−methyl−α−D−fructofuranose. Both are the name of the same structure.

Answer 47

Interpretation Introduction

(f)

Interpretation:

Whether the compounds, methyl α−D−fructofuranoside and 2−O−methyl−α−D−fructofuranose are enantiomers. epimers, anomers, enantiomers, diastereomers, constitutional isomers or none of the above is to be stated

Concept introduction:

Sugars show different types of isomerism between molecules. They may be enantiomers, epimers, anomers, or diastereomers depending upon chirality and plane of symmetry in molecules. It also depends on stereochemistry of different carbons. The naming of the same compound can be done in different manners.

Answer 48

Expert Solution

Answer to Problem 24.39AP

The compounds, methyl α−D−fructofuranoside and 2−O−methyl−α−D−fructofuranose are identical compounds only the way of naming is different.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 11

Answer 49

Expert Solution

Answer 50

Expert Solution

Answer 51

Expert Solution

Answer 52

Explanation of Solution

The structure of methyl α−D−fructofuranoside or 2−O−methyl−α−D−fructofuranose is shown below.

Organic Chemistry, Chapter 24, Problem 24.39AP , additional homework tip 12

Figure 6

So, the compound is same, they are identical. In first name it is taken as methyl derivative of α−D−fructofuranoside as in second name methyl is taken on carbon attached to oxygen atom which is again the α carbon on atom. They are identical compounds not isomers.

Answer 53

Conclusion

The compound shown in Figure 6 can be named as methyl α−D−fructofuranoside as well as 2−O−methyl−α−D−fructofuranose. Both are the name of the same structure.