Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 28, Problem 28.45P
Interpretation Introduction

(a)

Interpretation: The Haworth projection for β- D-talopyranoseby using given structures is to be drawn.

Concept introduction: The structural representation of sugar molecule in cyclic form is known as Haworth projection. Sugar molecule that has six-membered-ring is known as pyranose and sugar molecule that has five-membered-ring is called furanose.

Expert Solution
Check Mark

Answer to Problem 28.45P

The Haworth projection for β- D-talopyranoseby using given structures is,

Organic Chemistry, Chapter 28, Problem 28.45P , additional homework tip  1

Explanation of Solution

The structure of D-talose is,

Organic Chemistry, Chapter 28, Problem 28.45P , additional homework tip  2

Figure 1

The steps for the conversion of Fischer projection of D-talose into Haworth projection is as follow:

Step-1 Talopyranose ring is formed by the attack of OH substituent at C5 on the carbonyl carbon.

Step 2 The Haworth projection of D-talopyranose, CH2OH is drawn above the ring.

Step 3 In the beta-form, the substituents CH2OH and OH at C1 are cis to each other. Thus, both are drawn above the ring.

Step-4 The substituents which are present on the right side in the Fischer projection are drawn on the below the ring in the Haworth projection. Similarly, the substituents which are present on the left side in the Fischer projection are drawn on the above the ring in the Haworth projection.

The conversion of D-talose into β- D-talopyranose is shown below.

Organic Chemistry, Chapter 28, Problem 28.45P , additional homework tip  3

Figure 2

Conclusion

The Haworth projection for β- D-talopyranoseby using given structures is shown in Figure 2.

Interpretation Introduction

(b)

Interpretation: The Haworth projection for β- D-mannopyranoseby using given structure is to be drawn.

Concept introduction: The structural representation of sugar molecule in cyclic form is known as Haworth projection. Sugar molecule that has six-membered-ring is known as pyranose and sugar molecule that has five-membered-ring is called furanose.

Expert Solution
Check Mark

Answer to Problem 28.45P

The Haworth projection for β- D-mannopyranose by using given structure is,

Organic Chemistry, Chapter 28, Problem 28.45P , additional homework tip  4

Explanation of Solution

The structure of D-mannose is,

Organic Chemistry, Chapter 28, Problem 28.45P , additional homework tip  5

Figure 3

The steps for the conversion of Fischer projection of D-mannose into Haworth projection is as follow:

Step-1 Mannosepyranose ring is formed by the attack of OH substituent at C5 on the carbonyl carbon.

Step 2 The Haworth projection of D-mannosepyranose, CH2OH is drawn above the ring.

Step 3 In the beta-form, the substituents CH2OH and OH at C1 are cis to each other. Thus, both are drawn above the ring.

Step-4 The substituents which are present on the right side in the Fischer projection are drawn on the below the ring in the Haworth projection. Similarly, the substituents which are present on the left side in the Fischer projection are drawn on the above the ring in the Haworth projection.

The conversion of D-mannose into D-mannosepyranose is shown below.

Organic Chemistry, Chapter 28, Problem 28.45P , additional homework tip  6

Figure 4

Conclusion

The Haworth projection for β- D-mannosepyranose by using given structure is shown in Figure 4.

Interpretation Introduction

(c)

Interpretation: The Haworth projection for α- D-galactopyranose by using given structure is to be drawn.

Concept introduction: The structural representation of sugar molecule in cyclic form is known as Haworth projection. Sugar molecule that has six-membered-ring is known as pyranose and sugar molecule that has five-membered-ring is called furanose.

Expert Solution
Check Mark

Answer to Problem 28.45P

The Haworth projection for α- D-galactopyranose by using given structure is,

Organic Chemistry, Chapter 28, Problem 28.45P , additional homework tip  7

Explanation of Solution

The structure of D-galactose is,

Organic Chemistry, Chapter 28, Problem 28.45P , additional homework tip  8

Figure 5

The steps for the conversion of Fischer projection of D-galactose into Haworth projection is as follow:

Step-1 Galactopyranose ring is formed by the attack of OH substituent at C5 on the carbonyl carbon.

Step 2 The Haworth projection of D-galactopyranose, CH2OH is drawn above the ring.

Step 3 In the alpha-form, the substituents CH2OH and OH at C1 are trans to each other. Thus, both are drawn above the ring.

Step-4 The substituents which are present on the right side in the Fischer projection are drawn on the below the ring in the Haworth projection. Similarly, the substituents which are present on the left side in the Fischer projection are drawn on the above the ring in the Haworth projection.

The conversion of D-galactose into D-galactopyranose is shown below.

Organic Chemistry, Chapter 28, Problem 28.45P , additional homework tip  9

Figure 6

Conclusion

The Haworth projection for β- D-galactopyranose by using given structure is shown in Figure 6.

Interpretation Introduction

(d)

Interpretation: The Haworth projection for α- D-ribofuranose by using given structure is to be drawn.

Concept introduction: The structural representation of sugar molecule in cyclic form is known as Haworth projection. Sugar molecule that has six-membered-ring is known as pyranose and sugar molecule that has five-membered-ring is called furanose.

Expert Solution
Check Mark

Answer to Problem 28.45P

The Haworth projection for α- D-ribofuranose by using given structure is,

Organic Chemistry, Chapter 28, Problem 28.45P , additional homework tip  10

Explanation of Solution

The structure of D-ribose is,

Organic Chemistry, Chapter 28, Problem 28.45P , additional homework tip  11

Figure 7

The steps for the conversion of Fischer projection of D-ribose into Haworth projection is as follow:

Step-1 Ribofuranose ring is formed by the attack of OH substituent at C4 on the carbonyl carbon.

Step 2 The Haworth projection of D-ribofuranose, CH2OH is drawn above the ring.

Step 3 In the alpha-form, the substituents CH2OH and OH at C1 are trans to each other. Thus, both are drawn above the ring.

Step-4 The substituents which are present on the right side in the Fischer projection are drawn on the below the ring in the Haworth projection. Similarly, the substituents which are present on the left side in the Fischer projection are drawn on the above the ring in the Haworth projection.

The conversion of D-ribose into D-ribofuranose is shown below.

Organic Chemistry, Chapter 28, Problem 28.45P , additional homework tip  12

Figure 8

Conclusion

The Haworth projection for α- D-ribofuranose by using given structure is shown in Figure 8.

Interpretation Introduction

(e)

Interpretation: The Haworth projection for α- D-tagatofuranose by using given structure is to be drawn.

Concept introduction: The structural representation of sugar molecule in cyclic form is known as Haworth projection. Sugar molecule that has six-membered-ring is known as pyranose and sugar molecule that has five-membered-ring is called furanose.

Expert Solution
Check Mark

Answer to Problem 28.45P

The Haworth projection for α- D-tagatofuranose by using given structure is,

Organic Chemistry, Chapter 28, Problem 28.45P , additional homework tip  13

Explanation of Solution

The structure of D-tagatose is,

Organic Chemistry, Chapter 28, Problem 28.45P , additional homework tip  14

Figure 9

The steps for the conversion of Fischer projection of D-tagatose into Haworth projection is as follow:

Step-1 Tagatofuranose ring is formed by the attack of OH substituent at C5 on the carbonyl carbon.

Step 2 The Haworth projection of D-tagatofuranose, CH2OH is drawn above the ring.

Step 3 In the alpha-form, the substituents CH2OH and OH at C1 are trans to each other. Thus, both are drawn above the ring.

Step-4 The substituents which are present on the right side in the Fischer projection are drawn on the below the ring in the Haworth projection. Similarly, the substituents which are present on the left side in the Fischer projection are drawn on the above the ring in the Haworth projection.

The conversion of D-tagatose into D-tagatofuranose is shown below.

Organic Chemistry, Chapter 28, Problem 28.45P , additional homework tip  15

Figure 10

Conclusion

The Haworth projection for α- D-tagatofuranose by using given structure is shown in Figure 10.

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Chapter 28 Solutions

Organic Chemistry

Ch. 28 - Prob. 28.11PCh. 28 - Prob. 28.12PCh. 28 - Prob. 28.13PCh. 28 - Prob. 28.14PCh. 28 - Prob. 28.15PCh. 28 - Prob. 28.16PCh. 28 - Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.18PCh. 28 - Prob. 28.19PCh. 28 - Prob. 28.20PCh. 28 - Prob. 28.21PCh. 28 - Draw the products formed when D-arabinose is...Ch. 28 - Prob. 28.23PCh. 28 - Prob. 28.24PCh. 28 - Prob. 28.25PCh. 28 - Prob. 28.26PCh. 28 - Prob. 28.27PCh. 28 - Prob. 28.28PCh. 28 - Prob. 28.29PCh. 28 - Prob. 28.30PCh. 28 - Prob. 28.31PCh. 28 - Prob. 28.32PCh. 28 - Prob. 28.33PCh. 28 - Prob. 28.34PCh. 28 - Problem-28.35 Draw the structures of the...Ch. 28 - Prob. 28.36PCh. 28 - 28.37 Convert each ball-and-stick model to a...Ch. 28 - Prob. 28.38PCh. 28 - Prob. 28.39PCh. 28 - Convert each compound to a Fischer projection and...Ch. 28 - Prob. 28.41PCh. 28 - Prob. 28.42PCh. 28 - Prob. 28.43PCh. 28 - Prob. 28.44PCh. 28 - Prob. 28.45PCh. 28 - Draw both pyranose anomers of each aldohexose...Ch. 28 - Prob. 28.47PCh. 28 - Prob. 28.48PCh. 28 - Prob. 28.49PCh. 28 - Prob. 28.50PCh. 28 - Prob. 28.51PCh. 28 - Prob. 28.52PCh. 28 - Prob. 28.53PCh. 28 - What products are formed when each compound is...Ch. 28 - Prob. 28.55PCh. 28 - Prob. 28.56PCh. 28 - Prob. 28.57PCh. 28 - Prob. 28.58PCh. 28 - 28.58 Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.60PCh. 28 - Prob. 28.61PCh. 28 - Prob. 28.62PCh. 28 - Prob. 28.63PCh. 28 - Prob. 28.64PCh. 28 - Prob. 28.65PCh. 28 - Prob. 28.66PCh. 28 - Prob. 28.67PCh. 28 - Prob. 28.68PCh. 28 - Prob. 28.69PCh. 28 - Prob. 28.70PCh. 28 - Prob. 28.71PCh. 28 - Prob. 28.72PCh. 28 - Prob. 28.73PCh. 28 - Prob. 28.74PCh. 28 - Prob. 28.75PCh. 28 - Prob. 28.76PCh. 28 - Prob. 28.77PCh. 28 - Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.79P
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