Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 28, Problem 28.51P
Interpretation Introduction

(a)

Interpretation: The products formed by the treatment of D-altrose with CH3OH, HCl are to be drawn.

Concept introduction: The OH groups of monosaccharides on reaction with alcohol in the presence of strong acid results in the formation of acetals. Acetals are the groups in which carbon atom is bonded to two OR groups through single bonds. They are used as protecting groups for aldehyde and ketones.

Expert Solution
Check Mark

Answer to Problem 28.51P

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

Organic Chemistry, Chapter 28, Problem 28.51P , additional homework tip  1

Explanation of Solution

The OH groups of monosaccharides on reaction with alcohol in the presence of strong acid result in the formation of methoxy group. The products formed by the treatment of D- altrose with CH3OH, HCl are shown below.

Organic Chemistry, Chapter 28, Problem 28.51P , additional homework tip  2

Figure 1

Conclusion

The products formed by the treatment of D-altrose with CH3OH, HCl are shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: The products formed by the treatment of D-altrose with (CH3)2CHOH, HCl are to be drawn.

Concept introduction: The OH groups of monosaccharides on reaction with alcohol in the presence of strong acid results in the formation of acetals. Acetals are the groups in which carbon atom is bonded to two OR groups through single bonds. They are used as protecting groups for aldehyde and ketones.

Expert Solution
Check Mark

Answer to Problem 28.51P

The products formed by the treatment of D-altrose with (CH3)2CHOH, HCl are,

Organic Chemistry, Chapter 28, Problem 28.51P , additional homework tip  3

Explanation of Solution

The OH groups of monosaccharides on reaction with alcohol in the presence of strong acid result in the formation of acetal. Acetals are the groups in which carbon atom is bonded to two OR groups through single bonds. They are used as protecting groups for aldehyde and ketones.

The products formed by the treatment of D- altrose with (CH3)2CHOH, HCl are shown below.

Organic Chemistry, Chapter 28, Problem 28.51P , additional homework tip  4

Figure 2

Conclusion

The products formed by the treatment of D-altrose with (CH3)2CHOH, HCl are shown in Figure 2.

Interpretation Introduction

(c)

Interpretation: The products formed by the treatment of D-altrose with NaBH4, CH3OH are to be drawn.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Expert Solution
Check Mark

Answer to Problem 28.51P

The product formed by the treatment of D-altrose with NaBH4, CH3OH is,

Organic Chemistry, Chapter 28, Problem 28.51P , additional homework tip  5

Explanation of Solution

The product formed by the treatment of D-altrose with NaBH4, CH3OH is shown below.

Organic Chemistry, Chapter 28, Problem 28.51P , additional homework tip  6

Figure 3

In the given reaction, sodium borohydride is used as a reducing agent. Sodium borohydride is used to for the reduction of carbonyl compounds to alcohols.

Conclusion

The product formed by the treatment of D-altrose with NaBH4, CH3OH is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation: The products formed by the treatment of D-altrose with Br2, H2O are to be drawn.

Concept introduction: The aldehyde group of aldoses oxidizes to carboxyl group on treatment with Br2, H2O. The oxidation of aldoses leads to the formation of aldonic acid.

Expert Solution
Check Mark

Answer to Problem 28.51P

The product formed by the treatment of D-altrose with Br2, H2O is,

Organic Chemistry, Chapter 28, Problem 28.51P , additional homework tip  7

Explanation of Solution

The oxidation of aldehyde group of aldoses leads to the formation of aldonic acid, in which the terminal carbon atoms are substituted by carboxyl group and alcoholic group. The product formed by the treatment of D-altrose with Br2, H2O is shown below.

Organic Chemistry, Chapter 28, Problem 28.51P , additional homework tip  8

Figure 4

Conclusion

The product formed by the treatment of D-altrose with Br2, H2O is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation: The products formed by the treatment of D-altrose with HNO3, H2O are to be drawn.

Concept introduction: The aldehyde group and primary alcohol of aldoses oxidizes to carboxyl groups on treatment with warm HNO3. The oxidation of aldoses leads to the formation of aldaric acid.

Expert Solution
Check Mark

Answer to Problem 28.51P

The product formed by the treatment of D-altrose with HNO3, H2O is,

Organic Chemistry, Chapter 28, Problem 28.51P , additional homework tip  9

Explanation of Solution

The oxidation of aldehyde group and primary alcohol of aldoses leads to the formation of aldaric acid, in which the terminal carbon atoms are substituted by carboxyl groups. The product formed by the treatment of D-altrose with HNO3, H2O is shown below.

Organic Chemistry, Chapter 28, Problem 28.51P , additional homework tip  10

Figure 5

Conclusion

The product formed by the treatment of D-altrose with HNO3, H2O is shown in Figure 5.

Interpretation Introduction

(f)

Interpretation: The products formed by the treatment of D-altrose with [1] NH2OH, [2] (CH3CO)2O, NaOCOCH3 [3] NaOCH3 are to be drawn.

Concept introduction: The OH groups of monosaccharides on reaction with base and an alkyl halide convert into ether. A single product is formed during this reaction because the configuration of all substituents in the starting material is retained.

Expert Solution
Check Mark

Answer to Problem 28.51P

The product formed by the treatment of D-altrose with [1]NH2OH, [2] (CH3CO)2O, NaOCOCH3 [3] NaOCH3 are,

Organic Chemistry, Chapter 28, Problem 28.51P , additional homework tip  11

Explanation of Solution

The reaction of D-altrose with hydroxylamine results in the formation of oxime. The second step is the dehydration of oxime to nitriles. The reaction of nitrile with NaOCH3 results in the formation of aldehyde by the loss of HCN.

The product formed by the treatment of D-altrose with [1]NH2OH, [2] (CH3CO)2O, NaOCOCH3 [3] NaOCH3 are shown below.

Organic Chemistry, Chapter 28, Problem 28.51P , additional homework tip  12

Figure 6

Conclusion

The product formed by the treatment of D-altrose with [1]NH2OH, [2] (CH3CO)2O, NaOCOCH3 [3] NaOCH3 are shown in Figure 6.

Interpretation Introduction

(g)

Interpretation: The products formed by the treatment of D-altrose with [1]NaCN, HCl[2] H2, PdBaSO4 [3] H3O+ are to be drawn.

Concept introduction: The OH groups of monosaccharides on reaction with base and an alkyl halide convert into ether. A single product is formed during this reaction because the configuration of all substituents in the starting material is retained.

Expert Solution
Check Mark

Answer to Problem 28.51P

The products formed by the treatment of D-altrose with [1]NaCN, HCl[2] H2, PdBaSO4 [3] H3O+ are,

Organic Chemistry, Chapter 28, Problem 28.51P , additional homework tip  13

Explanation of Solution

The products formed by the treatment of D-altrose with [1]NaCN, HCl[2] H2, PdBaSO4 [3] H3O+ are shown below.

Organic Chemistry, Chapter 28, Problem 28.51P , additional homework tip  14

Figure 7

Conclusion

The products formed by the treatment of D-altrose with [1]NaCN, HCl[2] H2, PdBaSO4 [3] H3O+ are shown in Figure 7.

Interpretation Introduction

(h)

Interpretation: The products formed by the treatment of D-altrose with CH3I, Ag2O are to be drawn.

Concept introduction: The OH groups of monosaccharides on reaction with base and an alkyl halide convert into ether. A single product is formed during this reaction because the configuration of all substituents in the starting material is retained.

Expert Solution
Check Mark

Answer to Problem 28.51P

The products formed by the treatment of D-altrose with Ag2O, CH3I are,

Organic Chemistry, Chapter 28, Problem 28.51P , additional homework tip  15

Explanation of Solution

The OH groups of monosaccharides on reaction with base and an alkyl halide convert into ether. A single product is formed during this reaction because the configuration of all substituents in the starting material is retained. The products formed by the treatment of D- altrose with Ag2O, CH3I are shown below.

Organic Chemistry, Chapter 28, Problem 28.51P , additional homework tip  16

Figure 8

Conclusion

The products formed by the treatment of D-altrose with Ag2O, CH3I are shown in Figure 8.

Interpretation Introduction

(i)

Interpretation: The products formed by the treatment of D-altrose with Ac2O, pyridine are to be drawn.

Concept introduction: The OH groups of monosaccharides on reaction with base and an alkyl halide convert into ether. A single product is formed during this reaction because the configuration of all substituents in the starting material is retained.

Expert Solution
Check Mark

Answer to Problem 28.51P

The products formed by the treatment of D-altrose with Ac2O, pyridine are,

Organic Chemistry, Chapter 28, Problem 28.51P , additional homework tip  17

Explanation of Solution

The OH groups of monosaccharide on reaction with base are converted into ether. The products formed by the treatment of D- altrose with Ac2O, pyridine are shown below.

Organic Chemistry, Chapter 28, Problem 28.51P , additional homework tip  18

Figure 9

Conclusion

The products formed by the treatment of D-altrose with Ag2O, CH3I are shown in Figure 9.

Interpretation Introduction

(j)

Interpretation: The products formed by the treatment of D-altrose with C6H5CH2NH2, mild H+ are to be drawn.

Concept introduction: The OH groups of monosaccharides on reaction with amine in the presence of mild acid results in the formation of two anomers of glycoside.

Expert Solution
Check Mark

Answer to Problem 28.51P

The products formed by the treatment of D-altrose with C6H5CH2NH2, mild H+ are,

Organic Chemistry, Chapter 28, Problem 28.51P , additional homework tip  19

Explanation of Solution

The OH groups of monosaccharides on reaction with base and an alkyl halide convert into ether. The products formed by the treatment of D- altrose with C6H5CH2NH2, mild H+ are shown below.

Organic Chemistry, Chapter 28, Problem 28.51P , additional homework tip  20

Figure 10

Conclusion

The products formed by the treatment of D-altrose with C6H5CH2NH2, mild H+ are shown in Figure 10.

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Chapter 28 Solutions

Organic Chemistry

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