Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
Question
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Chapter 23.SE, Problem 23VC
Interpretation Introduction

a)

Organic Chemistry, Chapter 23.SE, Problem 23VC , additional homework tip  1

Interpretation:

Which aldehyde or ketone gives in an aldol reaction the compound represented by the model is to be stated.

Concept introduction:

Aldehydes with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α- carbon of one molecule and the carbonyl carbon of the second molecule. The product obtained is a β-hydroxyaldehyde.

To state:

Which aldehyde or ketone gives in an aldol reaction the compound represented by the model.

Expert Solution
Check Mark

Answer to Problem 23VC

The ketone that gives in an aldol reaction the compound represented by the model is 3-pentanone.

Explanation of Solution

The compound represented by the model is

Organic Chemistry, Chapter 23.SE, Problem 23VC , additional homework tip  2

An analysis of the structure indicates it can be produced by the aldol reaction between two 3-pentanone molecules and dehydrating the aldol obtained.

Organic Chemistry, Chapter 23.SE, Problem 23VC , additional homework tip  3

Conclusion

The ketone that gives in an aldol reaction the compound represented by the model is 3-pentanone.

Interpretation Introduction

b)

Organic Chemistry, Chapter 23.SE, Problem 23VC , additional homework tip  4

Interpretation:

Which aldehyde or ketone gives in an aldol reaction the compound represented by the model is to be stated.

Concept introduction:

Aldehydes with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α- carbon of one molecule and the carbonyl carbon of the second molecule. The product obtained is a β-hydroxyaldehyde.

To state:

Which aldehyde or ketone gives in an aldol reaction the compound represented by the model.

Expert Solution
Check Mark

Answer to Problem 23VC

The aldehyde that gives in an aldol reaction the compound represented by the model is 3-methylbutanal.

Explanation of Solution

The compound represented by the model is

Organic Chemistry, Chapter 23.SE, Problem 23VC , additional homework tip  5

An analysis of the structure indicates it can be produced by the aldol reaction between two 3-methylbutanal molecules and dehydrating the aldol obtained.

Organic Chemistry, Chapter 23.SE, Problem 23VC , additional homework tip  6

Conclusion

The aldehyde that gives in an aldol reaction, the compound represented by the model is 3-methylbutanal.

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Chapter 23 Solutions

Organic Chemistry

Ch. 23.7 - Show the products you would expect to obtain by...Ch. 23.7 - Prob. 12PCh. 23.8 - What product would you expect from the following...Ch. 23.9 - What product would you expect From the following...Ch. 23.9 - Prob. 15PCh. 23.10 - Prob. 16PCh. 23.10 - Prob. 17PCh. 23.10 - Prob. 18PCh. 23.11 - Prob. 19PCh. 23.11 - Show how you might use an enamine reaction to...Ch. 23.12 - Prob. 21PCh. 23.12 - How would you prepare the following compound using...Ch. 23.SE - Prob. 23VCCh. 23.SE - Prob. 24VCCh. 23.SE - Prob. 25VCCh. 23.SE - The following molecule was formed by a Robinson...Ch. 23.SE - Prob. 27MPCh. 23.SE - Prob. 28MPCh. 23.SE - Predict the product(s) and provide the mechanism...Ch. 23.SE - Predict the product(s) and provide the mechanism...Ch. 23.SE - Predict the product(s) and provide the mechanism...Ch. 23.SE - Knoevenagel condensation is a reaction involving...Ch. 23.SE - Azlactones are important starting materials used...Ch. 23.SE - Prob. 34MPCh. 23.SE - Isoleucine, another of the twenty amino acids...Ch. 23.SE - The first step in the citric acid cycle of food...Ch. 23.SE - Prob. 37MPCh. 23.SE - The Knoevenagel reaction is a carbonyl...Ch. 23.SE - The Darzens reaction invoIves a two-step,...Ch. 23.SE - The following reaction involves a hydrolysis...Ch. 23.SE - Prob. 41MPCh. 23.SE - Prob. 42MPCh. 23.SE - Prob. 43MPCh. 23.SE - Propose a mechanism for the following...Ch. 23.SE - Prob. 45MPCh. 23.SE - Prob. 46MPCh. 23.SE - Prob. 47MPCh. 23.SE - Prob. 48APCh. 23.SE - Prob. 49APCh. 23.SE - Prob. 50APCh. 23.SE - Prob. 51APCh. 23.SE - Prob. 52APCh. 23.SE - Prob. 53APCh. 23.SE - Prob. 54APCh. 23.SE - Prob. 55APCh. 23.SE - Prob. 56APCh. 23.SE - Prob. 57APCh. 23.SE - Prob. 58APCh. 23.SE - In the mixed Claisen reaction of cyclopentanone...Ch. 23.SE - Ethyl dimethylacetoacetate reacts instantly at...Ch. 23.SE - Prob. 61APCh. 23.SE - Prob. 62APCh. 23.SE - The so-called Wieland-Miescher ketone is a...Ch. 23.SE - Prob. 64APCh. 23.SE - Prob. 65APCh. 23.SE - Prob. 66APCh. 23.SE - What condensation products would you expect to...Ch. 23.SE - The following reactions are unlikely to provide...Ch. 23.SE - Fill in the missing reagents a-h in the following...Ch. 23.SE - Prob. 70APCh. 23.SE - Prob. 71APCh. 23.SE - Prob. 72APCh. 23.SE - Prob. 73AP
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