Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 28, Problem 28.50P
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 28.50P

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

Organic Chemistry, Chapter 28, Problem 28.50P , additional homework tip  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 28.50P , additional homework tip  2

Figure 1

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 28.50P

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

Organic Chemistry, Chapter 28, Problem 28.50P , additional homework tip  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 28.50P , additional homework tip  4

Figure 2

Conclusion

The products formed by the treatment of α- D-gulose with CH3OH, HCl are shown in Figure 2.

Interpretation Introduction

(c)

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 28.50P

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

Organic Chemistry, Chapter 28, Problem 28.50P , additional homework tip  5

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 28.50P , additional homework tip  6

Figure 3

Conclusion

The product formed by the treatment of α- D-gulose with Ac2O, pyridine is shown in Figure 3.

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 28.50P

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

Organic Chemistry, Chapter 28, Problem 28.50P , additional homework tip  7

Explanation of Solution

The first step is the conversion of hydroxyl groups of gulose into the ether groups in the presence of C6H5CH2OH, HCl. The corresponding reaction is shown below.

Organic Chemistry, Chapter 28, Problem 28.50P , additional homework tip  8

Figure 4

Conclusion

The products formed by the treatment of α- D-gulose with given reagent are shown in Figure 4.

Interpretation Introduction

(e)

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 28.50P

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

Organic Chemistry, Chapter 28, Problem 28.50P , additional homework tip  9

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 28.50P , additional homework tip  10

Figure 5

Conclusion

The products formed by the treatment of α- D-gulose with given reagent are shown in Figure 5.

Interpretation Introduction

(f)

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 28.50P

The product formed by the treatment of α- D-gulose with C6H5COCl, pyridine is,

Organic Chemistry, Chapter 28, Problem 28.50P , additional homework tip  11

Explanation of Solution

In the presence of C6H5COCl and pyridine, the conversion of alcoholic groups in α- D-gulose into esters takes place and forms a desired product. The corresponding reaction is shown below.

Organic Chemistry, Chapter 28, Problem 28.50P , additional homework tip  12

Figure 7

Conclusion

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

Interpretation Introduction

(g)

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 28.50P

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

Organic Chemistry, Chapter 28, Problem 28.50P , additional homework tip  13

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 28.50P , additional homework tip  14

Figure 8

Conclusion

The products formed by the treatment of α- D-gulose with given reagent are shown in Figure 8.

Interpretation Introduction

(h)

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 28.50P

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

Organic Chemistry, Chapter 28, Problem 28.50P , additional homework tip  15

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 28.50P , additional homework tip  16

Figure 9

Conclusion

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

Interpretation Introduction

(i)

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 28.50P

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

Organic Chemistry, Chapter 28, Problem 28.50P , additional homework tip  17

Explanation of Solution

The conversion of the product (g) in presence of C6H5CH2Cl, Ag2O takes place and forms the desired product. The corresponding chemical reaction is shown below.

Organic Chemistry, Chapter 28, Problem 28.50P , additional homework tip  18

Figure 10

Conclusion

The products formed by the treatment of α- D-gulose with given reagent are shown in Figure 10.

Interpretation Introduction

(j)

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 28.50P

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

Organic Chemistry, Chapter 28, Problem 28.50P , additional homework tip  19

Explanation of Solution

The conversion of the product (d) in presence of CH3I, Ag2O takes place and forms the desired product. The corresponding chemical reaction is shown below.

Organic Chemistry, Chapter 28, Problem 28.50P , additional homework tip  20

Figure 11

Conclusion

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

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Chapter 28 Solutions

Organic Chemistry

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