Chapter 22, Problem 29P

Interpretation Introduction

(a)

Interpretation: The aldol product that is formed from the given pair of starting materials by using ${}^{-}\text{OH}$, ${\text{H}}_{\text{2}}\text{O}$ 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 $\text{β}$-hydroxyaldehyde or $\text{β}$-hydroxyketone which on further dehydration gives the conjugated enone.

Answer to Problem 29P

The aldol product that is formed from the given pair of starting materials by using ${}^{-}\text{OH}$, ${\text{H}}_{\text{2}}\text{O}$ is shown below.

Explanation of Solution

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

Figure 1

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

Figure 2

The aldol product that is formed from the given pair of starting materials by using ${}^{-}\text{OH}$, ${\text{H}}_{\text{2}}\text{O}$ is shown as,

Figure 3

In this step, the base, ${}^{-}\text{OH}$ abstracts the proton from one of the methyl group of $3-\text{pentanone}$ 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 ${\text{H}}_{\text{2}}\text{O}$ 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 ${}^{-}\text{OH}$, ${\text{H}}_{\text{2}}\text{O}$ is shown in Figure 3.

Interpretation Introduction

(b)

Interpretation: The aldol product that is formed from the given pair of starting materials by using ${}^{-}\text{OH}$, ${\text{H}}_{\text{2}}\text{O}$ 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 $\text{β}$-hydroxyaldehyde or $\text{β}$-hydroxyketone which on further dehydration gives the conjugated enone.

Answer to Problem 29P

The aldol product that is formed from the given pair of starting materials by using ${}^{-}\text{OH}$, ${\text{H}}_{\text{2}}\text{O}$ is shown below.

Explanation of Solution

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

Figure 4

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

Figure 5

The aldol product that is formed from the given pair of starting materials by using ${}^{-}\text{OH}$, ${\text{H}}_{\text{2}}\text{O}$ is shown as,

Figure 6

In this step, the base, ${}^{-}\text{OH}$ 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 ${\text{H}}_{\text{2}}\text{O}$ 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 ${}^{-}\text{OH}$, ${\text{H}}_{\text{2}}\text{O}$ is shown in Figure 6.