Organic Chemistry
Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 24, Problem 24.8P

Draw the products formed in the crossed aldol reaction of phenylacetaldehyde ( C 6 H 5 CH 2 CHO ) with each compound: (a) CH 2 ( COOEt ) 2 ; (b) CH 2 ( COCH 3 ) 2 ; (c) CH 3 COCH 2 CN .

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The product that is formed in the given crossed aldol reaction of phenylacetaldehyde (C6H5CH2CHO) with CH2(COOEt)2 is to be drawn.

Concept introduction: The crossed aldol reaction takes place between the two different carbonyl compounds that is between two different aldehydes or two different ketones or one aldehyde and one ketone. The crossed aldol reaction takes place only if the carbonyl compound contains an acidic αhydrogen atom.

Answer to Problem 24.8P

The product that is formed in the given crossed aldol reaction of phenylacetaldehyde (C6H5CH2CHO) with CH2(COOEt)2 is,

Organic Chemistry, Chapter 24, Problem 24.8P , additional homework tip  1

Explanation of Solution

The product that is formed in the given crossed aldol reaction is shown below.

Organic Chemistry, Chapter 24, Problem 24.8P , additional homework tip  2

Figure 1

In this crossed aldol reaction, phenylacetaldehyde reacts with CH2(COOEt)2 in the presence of strong base, sodium ethoxide to form the unsaturated aldehydic compound. In this reaction, the base abstracts a proton from CH2(COOEt)2 that result in the formation of carbanion. Then, that carbanion reacts with phenylacetaldehyde to form a βhydroxy compound. The βhydroxy compound losses water molecule that leads to the formation of the desired unsaturated product.

Conclusion

The product that is formed in the given crossed aldol reaction of phenylacetaldehyde (C6H5CH2CHO) with CH2(COOEt)2 is shown in Figure 1.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The product that is formed in the given crossed aldol reaction of phenylacetaldehyde (C6H5CH2CHO) with CH2(COCH3)2 is to be drawn.

Concept introduction: The crossed aldol reaction takes place between the two different carbonyl compounds that is between two different aldehydes or two different ketones or one aldehyde and one ketone. The crossed aldol reaction takes place only if the carbonyl compound contains an acidic αhydrogen atom.

Answer to Problem 24.8P

The product that is formed in the given crossed aldol reaction of phenylacetaldehyde (C6H5CH2CHO) with CH2(COCH3)2 is,

Organic Chemistry, Chapter 24, Problem 24.8P , additional homework tip  3

Explanation of Solution

The product that is formed in the given crossed aldol reaction is shown below.

Organic Chemistry, Chapter 24, Problem 24.8P , additional homework tip  4

Figure 2

In this crossed aldol reaction, phenylacetaldehyde reacts with CH2(COCH3)2 in the presence of strong base, sodium ethoxide to form the unsaturated aldehydic compound. In this reaction, the base abstracts a proton from CH2(COCH3)2 that result in the formation of carbanion. Then, that carbanion reacts with phenylacetaldehyde to form a βhydroxy compound. The βhydroxy compound losses water molecule that leads to the formation of the desired unsaturated product.

Conclusion

The product that is formed in the given crossed aldol reaction of phenylacetaldehyde (C6H5CH2CHO) with CH2(COCH3)2 is shown in Figure 2.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The product that is formed in the given crossed aldol reaction of phenylacetaldehyde (C6H5CH2CHO) with CH3COCH2CN is to be drawn.

Concept introduction: The crossed aldol reaction takes place between the two different carbonyl compounds that is between two different aldehydes or two different ketones or one aldehyde and one ketone. The crossed aldol reaction takes place only if the carbonyl compound contains an acidic αhydrogen atom.

Answer to Problem 24.8P

The product that is formed in the given crossed aldol reaction of phenylacetaldehyde (C6H5CH2CHO) with CH3COCH2CN is,

Organic Chemistry, Chapter 24, Problem 24.8P , additional homework tip  5

Explanation of Solution

The product that is formed in the given crossed aldol reaction is shown below.

Organic Chemistry, Chapter 24, Problem 24.8P , additional homework tip  6

Figure 3

In this crossed aldol reaction, phenylacetaldehyde reacts with CH3COCH2CN in the presence of strong base, sodium ethoxide to form the unsaturated aldehydic compound. In this reaction, the base abstracts a proton from CH3COCH2CN that result in the formation of carbanion. Then, that carbanion reacts with phenylacetaldehyde to form a βhydroxy compound. The βhydroxy compound losses water molecule that leads to the formation of the desired unsaturated product.

Conclusion

The product that is formed in the given crossed aldol reaction of phenylacetaldehyde (C6H5CH2CHO) with CH3COCH2CN is shown in Figure 3.

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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 - Prob. 24.15PCh. 24 - Problem 24.16 What ester is formed when each...Ch. 24 - Prob. 24.17PCh. 24 - Prob. 24.18PCh. 24 - Draw the products of each reaction. a. b. Ch. 24 - Problem 24.20 Two steps in a synthesis of the...Ch. 24 - Prob. 24.21PCh. 24 - Problem 24.22 Which of the following compounds can...Ch. 24 - Prob. 24.23PCh. 24 - Problem 24.24 What starting materials are needed...Ch. 24 - Problem 24.25 Draw the products when each pair of...Ch. 24 - Prob. 24.26PCh. 24 - Problem 24.27 What starting materials are needed...Ch. 24 - Prob. 24.28PCh. 24 - 24.29 What steps are needed to convert A to B? Ch. 24 - Prob. 24.30PCh. 24 - 24.31 Draw the product formed in each directed...Ch. 24 - Prob. 24.32PCh. 24 - 24.33 What starting materials are needed to...Ch. 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 - 24.39 Draw the product formed from a Claisen...Ch. 24 - Prob. 24.40PCh. 24 - 24.41 Even though B contains three ester groups, a...Ch. 24 - Prob. 24.42PCh. 24 - Prob. 24.43PCh. 24 - 24.44 Vetivone is isolated from vetiver, a...Ch. 24 - Draw the product of each Robinson annulation from...Ch. 24 - Prob. 24.46PCh. 24 - 24.47 Draw the organic products formed in each...Ch. 24 - 24.48 Fill in the lettered reagents needed for...Ch. 24 - Prob. 24.49PCh. 24 - Prob. 24.50PCh. 24 - Prob. 24.51PCh. 24 - 24.52 Draw a stepwise mechanism for the following...Ch. 24 - Prob. 24.53PCh. 24 - Prob. 24.54PCh. 24 - Prob. 24.55PCh. 24 - Prob. 24.56PCh. 24 - Prob. 24.57PCh. 24 - Prob. 24.58PCh. 24 - Prob. 24.59PCh. 24 - 24.60 Devise a synthesis of each compound from the...Ch. 24 - 24.61 Devise a synthesis of each compound from...Ch. 24 - 24.62 Devise a synthesis of each compound from ,...Ch. 24 - Prob. 24.63PCh. 24 - Prob. 24.64PCh. 24 - 24.65 Answer the following questions about...Ch. 24 - Prob. 24.66PCh. 24 - Prob. 24.67PCh. 24 - Prob. 24.68PCh. 24 - 24.69 Devise a stepwise mechanism for the...Ch. 24 - 24.70 Draw a stepwise mechanism for the following...Ch. 24 - Prob. 24.71PCh. 24 - Prob. 24.72PCh. 24 - Prob. 24.73P
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