Chapter 24, Problem 24.7P

Interpretation Introduction

(a)

Interpretation:

The Fischer projection, Haworth projection, and a line-and wedge structure for $\alpha \text{-D-glucopyranose}$ are to be stated. The two possible chain conformations are to be drawn.

Concept introduction:

Fischer projection is the two dimensional structure of a three dimensional compound. In it, the substituents of an asymmetric center are shown on horizontal and vertical lines. Haworth projection is the condensed cyclic representation of glucose, consisting of a pyranose ring.

Answer to Problem 24.7P

The Fischer projection, Haworth projection, and a line-and wedge structure for $\alpha \text{-D-glucopyranose}$ are shown below.

Explanation of Solution

The Fischer projection of $\alpha \text{-D-glucopyranose}$ is shown below.

Figure 1

The Fischer projection of $\alpha \text{-D-glucopyranose}$ is converted into Haworth projection as shown below.

Figure 2

The chair conformation of $\alpha \text{-D-glucopyranose}$ is shown below.

Figure 3

Conclusion

The Fischer projection, Haworth projection, and a line-and wedge structure for $\alpha \text{-D-glucopyranose}$ are shown in Figure 1, Figure 2, and Figure 3.

Interpretation Introduction

(b)

Interpretation:

The Fischer projection, Haworth projection, and a line-and wedge structure for $\beta \text{-D-mannopyranose}$ are to be stated. The two possible chain conformations are to be drawn.

Concept introduction:

Fischer projection is the two dimensional structure of a three dimensional compound. In it, the substituents of an asymmetric center are shown on horizontal and vertical lines. Haworth projection is the condensed cyclic representation of glucose, consisting of a pyranose ring.

Answer to Problem 24.7P

The Fischer projection, Haworth projection, and a line-and wedge structure for $\beta \text{-D-mannopyranose}$ are shown below.

Explanation of Solution

The Fischer projection of $\beta \text{-D-mannopyranose}$ is shown below.

Figure 4

The Fischer projection of $\beta \text{-D-mannopyranose}$ is converted into Haworth projection as shown below.

Figure 5

The chair conformation of $\beta \text{-D-mannopyranose}$ is shown below.

Figure 6

Conclusion

The Fischer projection, Haworth projection, and a line-and wedge structure for $\beta \text{-D-mannopyranose}$ are shown in Figure 4, Figure 5, and Figure 6.

Interpretation Introduction

(c)

Interpretation:

The Fischer projection, Haworth projection, and a line-and wedge structure for $\beta \text{-D-xylofuranose}$ are to be stated.

Concept introduction:

Fischer projection is the two dimensional structure of a three dimensional compound. In it, the substituents of an asymmetric center are shown on horizontal and vertical lines. Haworth projection is the condensed cyclic representation of glucose, consisting of a pyranose ring.

Answer to Problem 24.7P

The Fischer projection, Haworth projection, and a line-and wedge structure for $\beta \text{-D-xylofuranose}$ are shown below.

Explanation of Solution

The Fischer projection of $\beta \text{-D-xylofuranose}$ is shown below.

Figure 7

The Fischer projection of $\beta \text{-D-xylofuranose}$ is converted into Haworth projection as shown below.

Figure 8

The chair conformation of $\beta \text{-D-xylofuranose}$ does not exist as it is a five carbon cyclic compound.

Conclusion

The Fischer projection, Haworth projection, and a line-and wedge structure for $\alpha \text{-D-glucopyranose}$ are shown in Figure 7, Figure 8.

Interpretation Introduction

(d)

Interpretation:

The Fischer projection, Haworth projection, and a line-and wedge structure for $\alpha \text{-D-fructopyranose}$ are to be stated. The two possible chain conformations are to be drawn.

Concept introduction:

Fischer projection is the two dimensional structure of a three dimensional compound. In it, the substituents of an asymmetric center are shown on horizontal and vertical lines. Haworth projection is the condensed cyclic representation of glucose, consisting of a pyranose ring.

Answer to Problem 24.7P

The Fischer projection, Haworth projection, and a line-and wedge structure for $\alpha \text{-D-fructopyranose}$ are shown below.

Explanation of Solution

The Fischer projection of $\alpha \text{-D-fructopyranose}$ is shown below.

Figure 9

The Fischer projection of $\alpha \text{-D-fructopyranose}$ is converted into Haworth projection as shown below.

Figure 10

The chair conformation of $\alpha \text{-D-fructopyranose}$ is shown below.

Figure 11

Conclusion

The Fischer projection, Haworth projection, and a line-and wedge structure for $\alpha \text{-D-fructopyranose}$ are shown in Figure 9, Figure 10, and Figure 11.

Interpretation Introduction

(e)

Interpretation:

The Fischer projection, Haworth projection, and a line-and wedge structure for $\alpha \text{-L-glucopyranose}$ are to be stated. The two possible chain conformations are to be drawn.

Concept introduction:

Fischer projection is the two dimensional structure of a three dimensional compound. In it, the substituents of an asymmetric center are shown on horizontal and vertical lines. Haworth projection is the condensed cyclic representation of glucose, consisting of a pyranose ring.

Answer to Problem 24.7P

The Fischer projection, Haworth projection, and a line-and wedge structure for $\alpha \text{-L-glucopyranose}$ are shown below.

Explanation of Solution

The Fischer projection of $\alpha \text{-L-glucopyranose}$ is shown below.

Figure 12

The Fischer projection of $\alpha \text{-L-glucopyranose}$ is converted into Haworth projection as shown below.

Figure 13

The chair conformation of $\alpha \text{-L-glucopyranose}$ is shown below.

Figure 14

Conclusion

The Fischer projection, Haworth projection, and a line-and wedge structure for $\alpha \text{-L-glucopyranose}$ are shown in Figure 12, Figure 13, and Figure 14.

Interpretation Introduction

(f)

Interpretation:

The Fischer projection, Haworth projection, and a line-and wedge structure for a mixture of the $\alpha \text{-}$ and $\beta \text{-}$ anomers of $\text{L-glucopyranose}$ are to be stated. The two possible chain conformations are to be drawn.

Concept introduction:

Fischer projection is the two dimensional structure of a three dimensional compound. In it, the substituents of an asymmetric center are shown on horizontal and vertical lines. Haworth projection is the condensed cyclic representation of glucose, consisting of a pyranose ring.

Answer to Problem 24.7P

The Fischer projection, Haworth projection, and a line-and wedge structure for a mixture of the $\alpha \text{-}$ and $\beta \text{-}$ anomers of $\text{L-glucopyranose}$ are shown below.

Explanation of Solution

The Fischer projection for a mixture of the $\alpha \text{-}$ and $\beta \text{-}$ anomers of $\text{L-glucopyranose}$ is shown below.

Figure 15

The Fischer projection for a mixture of the $\alpha \text{-}$ and $\beta \text{-}$ anomers of $\text{L-glucopyranose}$ is converted into Haworth projection as shown below.

Figure 16

The chair conformation for a mixture of the $\alpha \text{-}$ and $\beta \text{-}$ anomers of $\text{L-glucopyranose}$ is shown below.

Figure 17

Conclusion

The Fischer projection, Haworth projection, and a line-and wedge structure for $\alpha \text{-D-glucopyranose}$ are shown in Figure 15, Figure 16, and Figure 17.