Chapter 24, Problem 24.1P

Interpretation Introduction

(a)

Interpretation: The aldol product that formed by the given compound 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. It is necessary that the carbonyl compound must contain at least one $\text{α}-\text{hydrogen}$ atom to undergo aldol reaction.

Answer to Problem 24.1P

The aldol product that formed by the given compound is $3-\text{hydroxy}-2,4-\text{diphenylbutanal}$ as shown below.

Explanation of Solution

The aldol product that formed by the given compound is shown below.

Figure 1

In this aldol reaction, one equivalent of $2-\text{phenylacetaldehyde}$ is treated with strong base that results in the formation of resonance-stabilized enolate ion. The second equivalent of $2-\text{phenylacetaldehyde}$ is then reacts with enolate ion. After that, hydrolysis of the intermediate compound takes place that results the formation of the desired product, $3-\text{hydroxy}-2,4-\text{diphenylbutanal}$.

Conclusion

The aldol product that formed by the given compound is $3-\text{hydroxy}-2,4-\text{diphenylbutanal}$.

Interpretation Introduction

(b)

Interpretation: The aldol product that formed by the given compound 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. It is necessary that the carbonyl compound must contain at least one $\text{α}-\text{hydrogen}$ atom to undergo aldol reaction.

Answer to Problem 24.1P

The aldol product that formed by the given compound is $2-\left(tert-\text{butyl}\right)-3-\text{hydroxy}-5,5-\text{dimethylhexanal}$ as shown below.

Explanation of Solution

The aldol product that formed by the given compound is shown below.

Figure 2

In this aldol reaction, one equivalent of $3,3-\text{dimethylbutanal}$ is treated with strong base that results in the formation of resonance-stabilized enolate ion. The second equivalent of $3,3-\text{dimethylbutanal}$ is then reacts with enolate ion. After that, hydrolysis of the intermediate compound takes place that results the formation of the desired product, $2-\left(tert-\text{butyl}\right)-3-\text{hydroxy}-5,5-\text{dimethylhexanal}$.

Conclusion

The aldol product that formed by the given compound is $2-\left(tert-\text{butyl}\right)-3-\text{hydroxy}-5,5-\text{dimethylhexanal}$.

Interpretation Introduction

(c)

Interpretation: The aldol product that formed by the given compound 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. It is necessary that the carbonyl compound must contain at least one $\text{α}-\text{hydrogen}$ atom to undergo aldol reaction.

Answer to Problem 24.1P

The aldol product that formed by the given compound is $4-\text{hydroxy}-4-\text{methylpentan}-2-\text{one}$ as shown below.

Explanation of Solution

The aldol product that formed by the given compound is shown below.

Figure 3

In this aldol reaction, one equivalent of $\text{propane}-2-\text{one}$ is treated with strong base that results in the formation of resonance-stabilized enolate ion. The second equivalent of $\text{propane}-2-\text{one}$ is then reacts with enolate ion. After that, hydrolysis of the intermediate compound takes place that results the formation of the desired product, $4-\text{hydroxy}-4-\text{methylpentan}-2-\text{one}$.

Conclusion

The aldol product that formed by the given compound is $4-\text{hydroxy}-4-\text{methylpentan}-2-\text{one}$.

Interpretation Introduction

(d)

Interpretation: The aldol product that formed by the given compound 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. It is necessary that the carbonyl compound must contain at least one $\text{α}-\text{hydrogen}$ atom to undergo aldol reaction.

Answer to Problem 24.1P

The aldol product that formed by the given compound is $1\text{'}-\text{hydroxy}-\left[1,1\text{'}-\text{bi}\left(\text{cyclohexan}\right)\right]-2-\text{one}$ as shown below.

Explanation of Solution

The aldol product that formed by the given compound is shown below.

Figure 4

In this aldol reaction, one equivalent of cyclohexanone is treated with strong base that results in the formation of resonance-stabilized enolate ion. The second equivalent of cyclohexanone is then reacts with enolate ion. After that, hydrolysis of the intermediate compound takes place that results the formation of the desired product, $1\text{'}-\text{hydroxy}-\left[1,1\text{'}-\text{bi}\left(\text{cyclohexan}\right)\right]-2-\text{one}$.

Conclusion

The aldol product that formed by the given compound is $1\text{'}-\text{hydroxy}-\left[1,1\text{'}-\text{bi}\left(\text{cyclohexan}\right)\right]-2-\text{one}$.