Organic Chemistry (6th Edition)
Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 22, Problem 29P
Interpretation Introduction

(a)

Interpretation: The aldol product that is formed from the given pair of starting materials by using OH, H2O is to be drawn.

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
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Answer to Problem 29P

The aldol product that is formed from the given pair of starting materials by using OH, H2O is shown below.

Organic Chemistry (6th Edition), Chapter 22, Problem 29P , additional homework tip  1

Explanation of Solution

The given ball and stick model of the pair of compounds is shown as,

Organic Chemistry (6th Edition), Chapter 22, Problem 29P , additional homework tip  2

Figure 1

According to the given ball and stick model, the given pair of compounds is identified as,

Organic Chemistry (6th Edition), Chapter 22, Problem 29P , additional homework tip  3

Figure 2

The aldol product that is formed from the given pair of starting materials by using OH, H2O is shown as,

Organic Chemistry (6th Edition), Chapter 22, Problem 29P , additional homework tip  4

Figure 3

In this step, the base, OH abstracts the proton from one of the methyl group of 3pentanone that result into the formation of an enolate ion. The above formed enolate ion attacks the other carbonyl carbon atom of formaldehyde that acts as an electrophile. Then, the protonation of the negatively charged oxygen of the intermediate takes place with the help of H2O that result in the formation of the desired compound.

Conclusion

The aldol product that is formed from the given pair of starting materials by using OH, H2O is shown in Figure 3.

Interpretation Introduction

(b)

Interpretation: The aldol product that is formed from the given pair of starting materials by using OH, H2O is to be drawn.

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 29P

The aldol product that is formed from the given pair of starting materials by using OH, H2O is shown below.

Organic Chemistry (6th Edition), Chapter 22, Problem 29P , additional homework tip  5

Explanation of Solution

The given ball and stick model of the pair of compounds is shown as,

Organic Chemistry (6th Edition), Chapter 22, Problem 29P , additional homework tip  6

Figure 4

According to the given ball and stick model, the given pair of compounds is identified as,

Organic Chemistry (6th Edition), Chapter 22, Problem 29P , additional homework tip  7

Figure 5

The aldol product that is formed from the given pair of starting materials by using OH, H2O is shown as,

Organic Chemistry (6th Edition), Chapter 22, Problem 29P , additional homework tip  8

Figure 6

In this step, the base, OH abstracts the proton from one of the methyl group of cyclopentanone that result into the formation of an enolate ion. The above formed enolate ion attacks the other carbonyl carbon atom of benzaldehyde that acts as an electrophile. Then, the protonation of the negatively charged oxygen of the intermediate takes place with the help of H2O that result in the formation of the desired compound.

Conclusion

The aldol product that is formed from the given pair of starting materials by using OH, H2O is shown in Figure 6.

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Chapter 22 Solutions

Organic Chemistry (6th Edition)

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