Chapter 28, Problem 28.49P

Interpretation Introduction

(a)

Interpretation: The product formed by the treatment of $\text{α-}$ D-gulose with ${\text{CH}}_{\text{3}}\text{I, AgO}$ 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.

Answer to Problem 28.49P

The product formed by the treatment of $\text{α-}$ D-gulose with ${\text{CH}}_{\text{3}}\text{I, AgO}$ is,

Figure 1

Explanation of Solution

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

Figure 2

Conclusion

The product formed by the treatment of $\text{α-}$ D-gulose with ${\text{CH}}_{\text{3}}\text{I, AgO}$ is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: The product formed by the treatment of $\text{α-}$ D-gulose with ${\text{CH}}_{\text{3}}\text{OH, HCl}$ 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.

Answer to Problem 28.49P

The products formed by the treatment of $\text{α-}$ D-gulose with ${\text{CH}}_{\text{3}}\text{OH, HCl}$ are,

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.

Figure 4

Conclusion

The products formed by the treatment of $\text{α-}$ D-gulose with ${\text{CH}}_{\text{3}}\text{OH, HCl}$ are shown in Figure 3.

Interpretation Introduction

(c)

Interpretation: The product formed by the treatment of $\text{α-}$ D-gulose with ${\text{Ac}}_{\text{2}}\text{O}$, 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.

Answer to Problem 28.49P

The product formed by the treatment of $\text{α-}$ D-gulose with ${\text{Ac}}_{\text{2}}\text{O}$, pyridine is,

Figure 5

Explanation of Solution

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

Figure 6

Conclusion

The product formed by the treatment of $\text{α-}$ D-gulose with ${\text{Ac}}_{\text{2}}\text{O}$, pyridine is shown in Figure 5.

Interpretation Introduction

(d)

Interpretation: The product formed by the treatment of $\text{α-}$ 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.

Answer to Problem 28.49P

The products formed by the treatment of $\text{α-}$ D-gulose with given reagent are,

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 $\left(\text{a}\right)$ 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.

Figure 8

Conclusion

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

Interpretation Introduction

(e)

Interpretation: The product formed by the treatment of $\text{α-}$ 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.

Answer to Problem 28.49P

The products formed by the treatment of $\text{α-}$ D-gulose with given reagent are,

Figure 9

Explanation of Solution

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

Figure 10

Conclusion

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

Interpretation Introduction

(f)

Interpretation: The product formed by the treatment of $\text{α-}$ 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.

Answer to Problem 28.49P

The products formed by the treatment of $\text{α-}$ D-gulose with given reagent are,

Figure 11

Explanation of Solution

The conversion of hydroxyl groups of product $\left(\text{d}\right)$ into $-{\text{OCH}}_{\text{2}}{\text{C}}_{\text{6}}{\text{H}}_{\text{5}}$ groups takes place in presence of base and methyl iodide and forms the desired product. The corresponding reaction is shown below.

Figure 12

Conclusion

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