Organic Chemistry
Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Concept explainers

Question
Chapter 28, Problem 28.49P
Interpretation Introduction

(a)

Interpretation: The product formed by the treatment of α- D-gulose with CH3I, AgO is to be drawn.

Concept introduction: Monosaccharides are the small units of simple sugars. The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide.

Expert Solution
Check Mark

Answer to Problem 28.49P

The product formed by the treatment of α- D-gulose with CH3I, AgO is,

Organic Chemistry, Chapter 28, Problem 28.49P , additional homework tip  1

Figure 1

Explanation of Solution

The conversion of hydroxyl groups of α- D-gulose into the ether groups in presence of base and methyl iodide takes place. The corresponding chemical reaction is shown below.

Organic Chemistry, Chapter 28, Problem 28.49P , additional homework tip  2

Figure 2

Conclusion

The product formed by the treatment of α- D-gulose with CH3I, AgO is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: The product formed by the treatment of α- D-gulose with CH3OH, HCl reagent is to be drawn.

Concept introduction: Monosaccharides are the small units of simple sugars The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide.

Expert Solution
Check Mark

Answer to Problem 28.49P

The products formed by the treatment of α- D-gulose with CH3OH, HCl are,

Organic Chemistry, Chapter 28, Problem 28.49P , additional homework tip  3

Figure 3

Explanation of Solution

The two anomers are formed by the treatment of monosaccharides with methanol in the presence of hydrochloric acid. One product with methoxy group on the equatorial position and other product with methoxy group on the axial position. The corresponding chemical reaction is shown below.

Organic Chemistry, Chapter 28, Problem 28.49P , additional homework tip  4

Figure 4

Conclusion

The products formed by the treatment of α- D-gulose with CH3OH, HCl are shown in Figure 3.

Interpretation Introduction

(c)

Interpretation: The product formed by the treatment of α- D-gulose with Ac2O, pyridine reagent is to be drawn.

Concept introduction: Monosaccharides are the small units of simple sugars. The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide.

Expert Solution
Check Mark

Answer to Problem 28.49P

The product formed by the treatment of α- D-gulose with Ac2O, pyridine is,

Organic Chemistry, Chapter 28, Problem 28.49P , additional homework tip  5

Figure 5

Explanation of Solution

In the presence of acetic anhydride and pyridine, the conversion of alcoholic groups in α- D-gulose into acetate esters takes place and forms a desired product. The corresponding reaction is shown below.

Organic Chemistry, Chapter 28, Problem 28.49P , additional homework tip  6

Figure 6

Conclusion

The product formed by the treatment of α- D-gulose with Ac2O, pyridine is shown in Figure 5.

Interpretation Introduction

(d)

Interpretation: The product formed by the treatment of α- D-gulose with given reagent is to be drawn.

Concept introduction: Monosaccharides are the small units of simple sugars. The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide.

Expert Solution
Check Mark

Answer to Problem 28.49P

The products formed by the treatment of α- D-gulose with given reagent are,

Organic Chemistry, Chapter 28, Problem 28.49P , additional homework tip  7

Figure 7

Explanation of Solution

The first step is the conversion of hydroxyl groups of gulose into the ether groups in presence of base and methyl iodide as shown in Figure 2.

The product (a) undergoes hydrolysis which produces two products. One product with hydroxyl group on the equatorial position and other product with hydroxyl group on the axial position. The corresponding reaction is shown below.

Organic Chemistry, Chapter 28, Problem 28.49P , additional homework tip  8

Figure 8

Conclusion

The products formed by the treatment of α- D-gulose with given reagent are shown in Figure 7.

Interpretation Introduction

(e)

Interpretation: The product formed by the treatment of α- D-gulose with given reagent is to be drawn.

Concept introduction: Monosaccharides are the small units of simple sugars The hydroxyl groups of monosaccharides are converted into the ester groups in presence of base and acetic anhydride or acetyl chloride.

Expert Solution
Check Mark

Answer to Problem 28.49P

The products formed by the treatment of α- D-gulose with given reagent are,

Organic Chemistry, Chapter 28, Problem 28.49P , additional homework tip  9

Figure 9

Explanation of Solution

The conversion of alcoholic groups of product (b) into acetate esters in presence of acetic anhydride and pyridine takes place and forms the desired product. The corresponding chemical reaction is shown below.

Organic Chemistry, Chapter 28, Problem 28.49P , additional homework tip  10

Figure 10

Conclusion

The products formed by the treatment of α- D-gulose with given reagent are shown in Figure 9.

Interpretation Introduction

(f)

Interpretation: The product formed by the treatment of α- D-gulose with given reagent is to be drawn.

Concept introduction: Monosaccharides are the small units of simple sugars. The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide.

Expert Solution
Check Mark

Answer to Problem 28.49P

The products formed by the treatment of α- D-gulose with given reagent are,

Organic Chemistry, Chapter 28, Problem 28.49P , additional homework tip  11

Figure 11

Explanation of Solution

The conversion of hydroxyl groups of product (d) into -OCH2C6H5 groups takes place in presence of base and methyl iodide and forms the desired product. The corresponding reaction is shown below.

Organic Chemistry, Chapter 28, Problem 28.49P , additional homework tip  12

Figure 12

Conclusion

The products formed by the treatment of α- D-gulose with given reagent are shown in Figure 11.

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Students have asked these similar questions
Draw the products formed when a-D-gulose is treated with each reagent.a. CH3I, Ag2Ob. CH3OH, HClc. Ac2O, pyridined. The product in (a), then H3O+e. The product in (b), then Ac2O, pyridinef. The product in (d), then C6H5CH2Cl, Ag2O
Draw the products formed when α-D-gulose is treated with each reagent. a. CH3I, Ag2O b. CH3OH, HCl c. Ac2O, pyridine d. The product in (a), then H3O+ e. The product in (b), then Ac2O, pyridine f. The product in (d), then C6H5CH2Cl, Ag2O
What product is formed when D-Gulose is treated with a. CH3I, Ag2O b. The product in (a), then H3O+  c. The product in (b), then C6H5CH2Cl, Ag2O

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 - Prob. 28.17PCh. 28 - Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.19PCh. 28 - Prob. 28.20PCh. 28 - Prob. 28.21PCh. 28 - Prob. 28.22PCh. 28 - Draw the products formed when D-arabinose is...Ch. 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 - 28.40 Convert each compound to a Fischer...Ch. 28 - Prob. 28.41PCh. 28 - Prob. 28.42PCh. 28 - 28.43 Draw a Haworth projection for each compound...Ch. 28 - Prob. 28.44PCh. 28 - 28.45 Draw both pyranose anomers of each...Ch. 28 - Prob. 28.46PCh. 28 - Prob. 28.47PCh. 28 - Prob. 28.48PCh. 28 - Prob. 28.49PCh. 28 - 28.50 Draw the products formed when D-altrose is...Ch. 28 - Prob. 28.51PCh. 28 - Prob. 28.52PCh. 28 - Prob. 28.53PCh. 28 - Prob. 28.54PCh. 28 - Prob. 28.55PCh. 28 - Prob. 28.56PCh. 28 - Prob. 28.57PCh. 28 - 28.58 Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.59PCh. 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 - 28.71 Draw a stepwise mechanism for the following...
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