Chapter 24, Problem 24.28P

Interpretation Introduction

(a)

Interpretation: The product that is formed by the aldol reaction of the given starting material(s) 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 24.28P

The product that is formed by the aldol reaction of the given starting material(s) by using ${}^{-}\text{OH}$, ${\text{H}}_{\text{2}}\text{O}$ is $3-\text{hydroxy}-2,2,4-\text{trimethylpentanal}$.

Explanation of Solution

The product that is formed by the aldol reaction of the given starting material(s) by using ${}^{-}\text{OH}$, ${\text{H}}_{\text{2}}\text{O}$ is shown as,

Figure 1

In this reaction, one molecule of isobutyraldehyde is treated with the strong base that leads to the formation of a resonance-stabilized enolate ion. Then, this enolate ion reacts with the second molecule of isobutyraldehyde followed by the hydrolysis to form $3-\text{hydroxy}-2,2,4-\text{trimethylpentanal}$ as the desired product.

Conclusion

The product that is formed by the aldol reaction of the given starting material(s) by using ${}^{-}\text{OH}$, ${\text{H}}_{\text{2}}\text{O}$ is $3-\text{hydroxy}-2,2,4-\text{trimethylpentanal}$.

Interpretation Introduction

(b)

Interpretation: The product that is formed by the aldol reaction of the given starting material(s) 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 24.28P

The product that is formed by the aldol reaction of the given starting material(s) by using ${}^{-}\text{OH}$, ${\text{H}}_{\text{2}}\text{O}$ is $3-\text{hydroxy}-2,2-\text{dimethylpropanal}$.

Explanation of Solution

The product that is formed by the aldol reaction of the given starting material(s) by using ${}^{-}\text{OH}$, ${\text{H}}_{\text{2}}\text{O}$ is shown as,

Figure 2

In this reaction, the compound, isobutyraldehyde is treated with the strong base that leads to the formation of a resonance-stabilized enolate ion. Then, this enolate ion reacts with formaldehyde followed by the hydrolysis to form $3-\text{hydroxy}-2,2-\text{dimethylpropanal}$ as the desired product.

Conclusion

The product that is formed by the aldol reaction of the given starting material(s) by using ${}^{-}\text{OH}$, ${\text{H}}_{\text{2}}\text{O}$ is $3-\text{hydroxy}-2,2-\text{dimethylpropanal}$.

Interpretation Introduction

(c)

Interpretation: The product that is formed by the aldol reaction of the given starting material(s) 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 24.28P

The product that is formed by the aldol reaction of the given starting material(s) by using ${}^{-}\text{OH}$, ${\text{H}}_{\text{2}}\text{O}$ is $2-\left(\text{hydroxy}\left(\text{phenyl}\right)\text{methyl}\right)\text{butanal}$.

Explanation of Solution

The product that is formed by the aldol reaction of the given starting material(s) by using ${}^{-}\text{OH}$, ${\text{H}}_{\text{2}}\text{O}$ is shown as,

Figure 3

In this reaction, the compound, butyraldehyde is treated with the strong base that leads to the formation of a resonance-stabilized enolate ion. Then, this enolate ion reacts with benzaldehyde followed by the hydrolysis to form $2-\left(\text{hydroxy}\left(\text{phenyl}\right)\text{methyl}\right)\text{butanal}$ as the desired product.

Conclusion

The product that is formed by the aldol reaction of the given starting material(s) by using ${}^{-}\text{OH}$, ${\text{H}}_{\text{2}}\text{O}$ is $2-\left(\text{hydroxy}\left(\text{phenyl}\right)\text{methyl}\right)\text{butanal}$.

Interpretation Introduction

(d)

Interpretation: The product that is formed by the aldol reaction of the given starting material(s) 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 24.28P

The product that is formed by the aldol reaction of the given starting material(s) by using ${}^{-}\text{OH}$, ${\text{H}}_{\text{2}}\text{O}$ is shown below.

Explanation of Solution

The product that is formed by the aldol reaction of the given starting material(s) by using ${}^{-}\text{OH}$, ${\text{H}}_{\text{2}}\text{O}$ is shown as,

Figure 4

In this reaction, one molecule of pentan-$3$-one is treated with the strong base that leads to the formation of a resonance-stabilized enolate ion. Then, this enolate ion reacts with the second molecule of pentan-$3$-one followed by the hydrolysis to form the desired $\text{β}$-hydroxyketone.

Conclusion

The product that is formed by the aldol reaction of the given starting material(s) by using ${}^{-}\text{OH}$, ${\text{H}}_{\text{2}}\text{O}$ is shown in Figure 4.