(a) Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted. Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry . In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β -hydroxyaldehyde or β -hydroxyketone which on further dehydration gives the conjugated enone.

Question

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Answer 1

Question

Chapter 24, Problem 24.9P

Interpretation Introduction

(a)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 1

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 2

Figure 1

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 3

Figure 2

Thus, the reagent that is needed to convert 2−ethyl−3−hydroxyhexanal to the given compound is sodium borohydride present in the solution of methanol. In this reaction, 2−ethyl−3−hydroxyhexanal gets reduced by sodium borohydride that results in the formation of a primary alcohol as the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 2.

Interpretation Introduction

(b)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 4

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown in Figure 1.

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 5

Figure 3

In this reaction, 2−ethyl−3−hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2−ethylhex−2−enal. The compound, 2−ethylhex−2−enal reacts with dimethyl lithium cuprate followed by the hydrolysis that results in the formation of the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 3.

Interpretation Introduction

(c)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 6

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown in Figure 1.

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 7

Figure 4

In this reaction, 2−ethyl−3−hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2−ethylhex−2−enal. The compound, 2−ethylhex−2−enal reacts with sodium borohydride followed by the hydrolysis that results in the formation of the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 4.

Interpretation Introduction

(d)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 8

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown in Figure 1.

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 9

Figure 5

In this reaction, 2−ethyl−3−hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2−ethylhex−2−enal. The compound, 2−ethylhex−2−enal reacts with methylmagnesium bromide followed by the hydrolysis that results in the formation of the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 5.

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Answer 2

Question

Chapter 24, Problem 24.9P

Interpretation Introduction

(a)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 1

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 2

Figure 1

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 3

Figure 2

Thus, the reagent that is needed to convert 2−ethyl−3−hydroxyhexanal to the given compound is sodium borohydride present in the solution of methanol. In this reaction, 2−ethyl−3−hydroxyhexanal gets reduced by sodium borohydride that results in the formation of a primary alcohol as the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 2.

Interpretation Introduction

(b)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 4

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown in Figure 1.

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 5

Figure 3

In this reaction, 2−ethyl−3−hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2−ethylhex−2−enal. The compound, 2−ethylhex−2−enal reacts with dimethyl lithium cuprate followed by the hydrolysis that results in the formation of the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 3.

Interpretation Introduction

(c)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 6

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown in Figure 1.

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 7

Figure 4

In this reaction, 2−ethyl−3−hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2−ethylhex−2−enal. The compound, 2−ethylhex−2−enal reacts with sodium borohydride followed by the hydrolysis that results in the formation of the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 4.

Interpretation Introduction

(d)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 8

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown in Figure 1.

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 9

Figure 5

In this reaction, 2−ethyl−3−hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2−ethylhex−2−enal. The compound, 2−ethylhex−2−enal reacts with methylmagnesium bromide followed by the hydrolysis that results in the formation of the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 5.

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Answer 3

Question

Chapter 24, Problem 24.9P

Interpretation Introduction

(a)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 1

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 2

Figure 1

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 3

Figure 2

Thus, the reagent that is needed to convert 2−ethyl−3−hydroxyhexanal to the given compound is sodium borohydride present in the solution of methanol. In this reaction, 2−ethyl−3−hydroxyhexanal gets reduced by sodium borohydride that results in the formation of a primary alcohol as the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 2.

Interpretation Introduction

(b)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 4

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown in Figure 1.

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 5

Figure 3

In this reaction, 2−ethyl−3−hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2−ethylhex−2−enal. The compound, 2−ethylhex−2−enal reacts with dimethyl lithium cuprate followed by the hydrolysis that results in the formation of the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 3.

Interpretation Introduction

(c)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 6

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown in Figure 1.

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 7

Figure 4

In this reaction, 2−ethyl−3−hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2−ethylhex−2−enal. The compound, 2−ethylhex−2−enal reacts with sodium borohydride followed by the hydrolysis that results in the formation of the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 4.

Interpretation Introduction

(d)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 8

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown in Figure 1.

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 9

Figure 5

In this reaction, 2−ethyl−3−hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2−ethylhex−2−enal. The compound, 2−ethylhex−2−enal reacts with methylmagnesium bromide followed by the hydrolysis that results in the formation of the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 5.

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Answer 4

Question

Chapter 24, Problem 24.9P

Interpretation Introduction

(a)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 1

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 2

Figure 1

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 3

Figure 2

Thus, the reagent that is needed to convert 2−ethyl−3−hydroxyhexanal to the given compound is sodium borohydride present in the solution of methanol. In this reaction, 2−ethyl−3−hydroxyhexanal gets reduced by sodium borohydride that results in the formation of a primary alcohol as the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 2.

Interpretation Introduction

(b)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 4

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown in Figure 1.

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 5

Figure 3

In this reaction, 2−ethyl−3−hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2−ethylhex−2−enal. The compound, 2−ethylhex−2−enal reacts with dimethyl lithium cuprate followed by the hydrolysis that results in the formation of the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 3.

Interpretation Introduction

(c)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 6

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown in Figure 1.

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 7

Figure 4

In this reaction, 2−ethyl−3−hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2−ethylhex−2−enal. The compound, 2−ethylhex−2−enal reacts with sodium borohydride followed by the hydrolysis that results in the formation of the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 4.

Interpretation Introduction

(d)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 8

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown in Figure 1.

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 9

Figure 5

In this reaction, 2−ethyl−3−hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2−ethylhex−2−enal. The compound, 2−ethylhex−2−enal reacts with methylmagnesium bromide followed by the hydrolysis that results in the formation of the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 5.

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Answer 5

Chapter 24, Problem 24.9P

Interpretation Introduction

(a)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 1

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 2

Figure 1

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 3

Figure 2

Thus, the reagent that is needed to convert 2−ethyl−3−hydroxyhexanal to the given compound is sodium borohydride present in the solution of methanol. In this reaction, 2−ethyl−3−hydroxyhexanal gets reduced by sodium borohydride that results in the formation of a primary alcohol as the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 2.

Interpretation Introduction

(b)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 4

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown in Figure 1.

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 5

Figure 3

In this reaction, 2−ethyl−3−hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2−ethylhex−2−enal. The compound, 2−ethylhex−2−enal reacts with dimethyl lithium cuprate followed by the hydrolysis that results in the formation of the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 3.

Interpretation Introduction

(c)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 6

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown in Figure 1.

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 7

Figure 4

In this reaction, 2−ethyl−3−hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2−ethylhex−2−enal. The compound, 2−ethylhex−2−enal reacts with sodium borohydride followed by the hydrolysis that results in the formation of the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 4.

Interpretation Introduction

(d)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 8

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown in Figure 1.

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 9

Figure 5

In this reaction, 2−ethyl−3−hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2−ethylhex−2−enal. The compound, 2−ethylhex−2−enal reacts with methylmagnesium bromide followed by the hydrolysis that results in the formation of the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 5.

Answer 6

Chapter 24, Problem 24.9P

Interpretation Introduction

(a)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 1

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 2

Figure 1

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 3

Figure 2

Thus, the reagent that is needed to convert 2−ethyl−3−hydroxyhexanal to the given compound is sodium borohydride present in the solution of methanol. In this reaction, 2−ethyl−3−hydroxyhexanal gets reduced by sodium borohydride that results in the formation of a primary alcohol as the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 2.

Answer 7

Chapter 24, Problem 24.9P

Interpretation Introduction

(a)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Answer 8

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 1

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 2

Figure 1

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 3

Figure 2

Thus, the reagent that is needed to convert 2−ethyl−3−hydroxyhexanal to the given compound is sodium borohydride present in the solution of methanol. In this reaction, 2−ethyl−3−hydroxyhexanal gets reduced by sodium borohydride that results in the formation of a primary alcohol as the desired product.

Answer 13

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 2.

Answer 14

Interpretation Introduction

(b)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 4

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown in Figure 1.

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 5

Figure 3

In this reaction, 2−ethyl−3−hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2−ethylhex−2−enal. The compound, 2−ethylhex−2−enal reacts with dimethyl lithium cuprate followed by the hydrolysis that results in the formation of the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 3.

Answer 15

Interpretation Introduction

(b)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Answer 16

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 4

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown in Figure 1.

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 5

Figure 3

In this reaction, 2−ethyl−3−hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2−ethylhex−2−enal. The compound, 2−ethylhex−2−enal reacts with dimethyl lithium cuprate followed by the hydrolysis that results in the formation of the desired product.

Answer 21

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 3.

Answer 22

Interpretation Introduction

(c)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 6

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown in Figure 1.

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 7

Figure 4

In this reaction, 2−ethyl−3−hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2−ethylhex−2−enal. The compound, 2−ethylhex−2−enal reacts with sodium borohydride followed by the hydrolysis that results in the formation of the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 4.

Answer 23

Interpretation Introduction

(c)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Answer 24

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 6

Answer 25

Expert Solution

Answer 26

Expert Solution

Answer 27

Expert Solution

Answer 28

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown in Figure 1.

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 7

Figure 4

In this reaction, 2−ethyl−3−hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2−ethylhex−2−enal. The compound, 2−ethylhex−2−enal reacts with sodium borohydride followed by the hydrolysis that results in the formation of the desired product.

Answer 29

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 4.

Answer 30

Interpretation Introduction

(d)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 8

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown in Figure 1.

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 9

Figure 5

In this reaction, 2−ethyl−3−hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2−ethylhex−2−enal. The compound, 2−ethylhex−2−enal reacts with methylmagnesium bromide followed by the hydrolysis that results in the formation of the desired product.

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 5.

Answer 31

Interpretation Introduction

(d)

Interpretation: The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is to be shown. The reagents that are needed to convert the obtained product to the given compound are to be predicted.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Answer 32

Expert Solution

Answer to Problem 24.9P

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown below:

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 8

Answer 33

Expert Solution

Answer 34

Expert Solution

Answer 35

Expert Solution

Answer 36

Explanation of Solution

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is shown in Figure 1.

In this reaction, first of all, one equivalent of butanal is treated with the strong base that results in the formation of a resonance-stabilized enolate ion. This enolate ion reacts with the second equivalent of butanal followed by the hydrolysis that leads to the formation of the desired product, 2−ethyl−3−hydroxyhexanal.

The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown as,

ORGANIC CHEMISTRY, Chapter 24, Problem 24.9P , additional homework tip 9

Figure 5

In this reaction, 2−ethyl−3−hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2−ethylhex−2−enal. The compound, 2−ethylhex−2−enal reacts with methylmagnesium bromide followed by the hydrolysis that results in the formation of the desired product.

Answer 37

Conclusion

The aldol product that is formed by the reaction of the two molecules of butanal in the presence of base is 2−ethyl−3−hydroxyhexanal. The reagents that are needed to convert 2−ethyl−3−hydroxyhexanal to the given compound are shown in Figure 5.

Answer 38

Ch. 24 - Prob. 24.1P Ch. 24 - Prob. 24.2P Ch. 24 - Problem 24.3 What unsaturated carbonyl compound is...Ch. 24 - Prob. 24.4P Ch. 24 - Prob. 24.5P Ch. 24 - Prob. 24.6P Ch. 24 - Problem 24.7 Draw the products formed in each...Ch. 24 - Problem 24.8 Draw the products formed in the...Ch. 24 - Prob. 24.9P Ch. 24 - Prob. 24.10P

Answer to Problem 24.9P

Explanation of Solution

Answer to Problem 24.9P

Explanation of Solution

Answer to Problem 24.9P

Explanation of Solution

Answer to Problem 24.9P

Explanation of Solution

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