Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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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
Check Mark

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 2ethyl3hydroxyhexanal. The reagents that are needed to convert 2ethyl3hydroxyhexanal 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, 2ethyl3hydroxyhexanal.

The reagents that are needed to convert 2ethyl3hydroxyhexanal 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 2ethyl3hydroxyhexanal to the given compound is sodium borohydride present in the solution of methanol. In this reaction, 2ethyl3hydroxyhexanal 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 2ethyl3hydroxyhexanal. The reagents that are needed to convert 2ethyl3hydroxyhexanal 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
Check Mark

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 2ethyl3hydroxyhexanal. The reagents that are needed to convert 2ethyl3hydroxyhexanal 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, 2ethyl3hydroxyhexanal.

The reagents that are needed to convert 2ethyl3hydroxyhexanal to the given compound are shown as,

Organic Chemistry, Chapter 24, Problem 24.9P , additional homework tip  5

Figure 3

In this reaction, 2ethyl3hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2ethylhex2enal. The compound, 2ethylhex2enal 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 2ethyl3hydroxyhexanal. The reagents that are needed to convert 2ethyl3hydroxyhexanal 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
Check Mark

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 2ethyl3hydroxyhexanal. The reagents that are needed to convert 2ethyl3hydroxyhexanal 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, 2ethyl3hydroxyhexanal.

The reagents that are needed to convert 2ethyl3hydroxyhexanal to the given compound are shown as,

Organic Chemistry, Chapter 24, Problem 24.9P , additional homework tip  7

Figure 4

In this reaction, 2ethyl3hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2ethylhex2enal. The compound, 2ethylhex2enal 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 2ethyl3hydroxyhexanal. The reagents that are needed to convert 2ethyl3hydroxyhexanal 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
Check Mark

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 2ethyl3hydroxyhexanal. The reagents that are needed to convert 2ethyl3hydroxyhexanal 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, 2ethyl3hydroxyhexanal.

The reagents that are needed to convert 2ethyl3hydroxyhexanal to the given compound are shown as,

Organic Chemistry, Chapter 24, Problem 24.9P , additional homework tip  9

Figure 5

In this reaction, 2ethyl3hydroxyhexanal undergoes dehydration in the presence of a base that leads to the formation of 2ethylhex2enal. The compound, 2ethylhex2enal 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 2ethyl3hydroxyhexanal. The reagents that are needed to convert 2ethyl3hydroxyhexanal to the given compound are shown in Figure 5.

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Chapter 24 Solutions

Organic Chemistry

Ch. 24 - Prob. 24.11PCh. 24 - Prob. 24.12PCh. 24 - Prob. 24.13PCh. 24 - Prob. 24.14PCh. 24 - Problem 24.16 What ester is formed when each...Ch. 24 - What crossed Claisen product is formed from each...Ch. 24 - Prob. 24.17PCh. 24 - Draw the products of each reaction. a. b. Ch. 24 - Problem 24.20 Two steps in a synthesis of the...Ch. 24 - Prob. 24.20PCh. 24 - Problem 24.22 Which of the following compounds can...Ch. 24 - What product is formed when each pair of compounds...Ch. 24 - Problem 24.24 What starting materials are needed...Ch. 24 - Problem 24.25 Draw the products when each pair of...Ch. 24 - Problem 24.27 What starting materials are needed...Ch. 24 - Prob. 24.26PCh. 24 - 24.29 What steps are needed to convert A to B? Ch. 24 - Prob. 24.28PCh. 24 - Prob. 24.29PCh. 24 - 24.31 Draw the product formed in each directed...Ch. 24 - Prob. 24.31PCh. 24 - What starting materials are needed to synthesize...Ch. 24 - Prob. 24.33PCh. 24 - Prob. 24.34PCh. 24 - Prob. 24.35PCh. 24 - 24.36 Identify the structures of C and D in the...Ch. 24 - Prob. 24.37PCh. 24 - Prob. 24.38PCh. 24 - Prob. 24.39PCh. 24 - Draw the product formed from a Claisen reaction...Ch. 24 - Prob. 24.41PCh. 24 - 24.41 Even though B contains three ester groups, a...Ch. 24 - Prob. 24.43PCh. 24 - What starting materials are needed to prepare each...Ch. 24 - 24.44 Vetivone is isolated from vetiver, a...Ch. 24 - Draw the product of each Robinson annulation from...Ch. 24 - Prob. 24.47PCh. 24 - Draw the organic products formed when butanal...Ch. 24 - 24.47 Draw the organic products formed in each...Ch. 24 - 24.48 Fill in the lettered reagents needed for...Ch. 24 - Prob. 24.51PCh. 24 - Prob. 24.52PCh. 24 - Prob. 24.53PCh. 24 - Draw a stepwise mechanism for the following...Ch. 24 - Prob. 24.55PCh. 24 - Prob. 24.56PCh. 24 - Prob. 24.57PCh. 24 - Prob. 24.58PCh. 24 - Prob. 24.59PCh. 24 - Prob. 24.60PCh. 24 - Prob. 24.61PCh. 24 - Prob. 24.62PCh. 24 - Devise a synthesis of each compound from...Ch. 24 - Prob. 24.64PCh. 24 - Prob. 24.65PCh. 24 - Prob. 24.66PCh. 24 - 24.65 Answer the following questions about...Ch. 24 - Prob. 24.68PCh. 24 - Prob. 24.69PCh. 24 - Prob. 24.70PCh. 24 - Prob. 24.71PCh. 24 - 24.70 Draw a stepwise mechanism for the following...Ch. 24 - Prob. 24.73PCh. 24 - Prob. 24.74PCh. 24 - Prob. 24.75P
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