Chapter 23, Problem 23.9P

Interpretation Introduction

(a)

Interpretation: The enolates that are formed by the reaction of the given ketone with LDA present in the THF solution and with ${\text{NaOCH}}_{\text{3}}$ present in ${\text{CH}}_{\text{3}}\text{OH}$ solution are to be identified.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The nucleophilic reaction that consists of bimolecular as well as bond-making and bond-breaking steps is termed as ${\text{S}}_{\text{N}}\text{2}$ reactions. This is a one-step reaction in which both nucleophile and substrate participate in the rate determining step.

The bulky base like LDA always abstracts the proton from the side of less substituted $\text{C}-\text{atom}$. The strong base, ${\text{NaOCH}}_{\text{3}}$ which is present in protic solvent like ${\text{CH}}_{\text{3}}\text{OH}$ always favors the elimination of the proton from the side of more substituted $\text{C}-\text{atom}$.

Answer to Problem 23.9P

The enolates that are formed by the reaction of the given ketone with LDA present in the THF solution and with ${\text{NaOCH}}_{\text{3}}$ present in ${\text{CH}}_{\text{3}}\text{OH}$ solution are shown below:

Explanation of Solution

The enolate that is formed by the reaction of the given ketone with LDA present in the THF solution is shown is shown as,

Figure 1

In this reaction, the given ketone is treated with LDA in the presence of THF solution to form an enolate ion. The strong base, LDA abstracts a proton from the less substituted carbon atom of the compound.

The enolate that is formed by the reaction of the given ketone with ${\text{NaOCH}}_{\text{3}}$ present in ${\text{CH}}_{\text{3}}\text{OH}$ solution is shown is shown as,

Figure 2

In this reaction, the given ketone is treated with ${\text{NaOCH}}_{\text{3}}$ present in ${\text{CH}}_{\text{3}}\text{OH}$ solution to form an enolate ion. The strong base, ${\text{NaOCH}}_{\text{3}}$ abstracts a proton from the more substituted carbon atom of the compound.

Conclusion

The enolates that are formed by the reaction of the given ketone with LDA present in the THF solution and with ${\text{NaOCH}}_{\text{3}}$ present in ${\text{CH}}_{\text{3}}\text{OH}$ solution are shown in Figure 1 and Figure 2.

Interpretation Introduction

(b)

Interpretation: The enolates that are formed by the reaction of the given ketone with LDA present in the THF solution and with ${\text{NaOCH}}_{\text{3}}$ present in ${\text{CH}}_{\text{3}}\text{OH}$ solution are to be identified.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The nucleophilic reaction that consists of bimolecular as well as bond-making and bond-breaking steps is termed as ${\text{S}}_{\text{N}}\text{2}$ reactions. This is a one-step reaction in which both nucleophile and substrate participate in the rate determining step.

The bulky base like LDA always abstracts the proton from the side of less substituted $\text{C}-\text{atom}$. The strong base, ${\text{NaOCH}}_{\text{3}}$ which is present in protic solvent like ${\text{CH}}_{\text{3}}\text{OH}$ always favors the elimination of the proton from the side of more substituted $\text{C}-\text{atom}$.

Answer to Problem 23.9P

The enolates that are formed by the reaction of the given ketone with LDA present in the THF solution and with ${\text{NaOCH}}_{\text{3}}$ present in ${\text{CH}}_{\text{3}}\text{OH}$ solution are shown below:

Explanation of Solution

The enolate that is formed by the reaction of the given ketone with LDA present in the THF solution is shown is shown as,

Figure 3

In this reaction, the given ketone is treated with LDA in the presence of THF solution to form an enolate ion. The strong base, LDA abstracts a proton from the less substituted carbon atom of the compound.

The enolate that is formed by the reaction of the given ketone with ${\text{NaOCH}}_{\text{3}}$ present in ${\text{CH}}_{\text{3}}\text{OH}$ solution is shown is shown as,

Figure 4

In this reaction, the given ketone is treated with ${\text{NaOCH}}_{\text{3}}$ present in ${\text{CH}}_{\text{3}}\text{OH}$ solution to form an enolate ion. The strong base, ${\text{NaOCH}}_{\text{3}}$ abstracts a proton from the more substituted carbon atom of the compound.

Conclusion

The enolates that are formed by the reaction of the given ketone with LDA present in the THF solution and with ${\text{NaOCH}}_{\text{3}}$ present in ${\text{CH}}_{\text{3}}\text{OH}$ solution are shown in Figure 3 and Figure 4.

Interpretation Introduction

(c)

Interpretation: The enolates that are formed by the reaction of the given ketone with LDA present in the THF solution and with ${\text{NaOCH}}_{\text{3}}$ present in ${\text{CH}}_{\text{3}}\text{OH}$ solution are to be identified.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The nucleophilic reaction that consists of bimolecular as well as bond-making and bond-breaking steps is termed as ${\text{S}}_{\text{N}}\text{2}$ reactions. This is a one-step reaction in which both nucleophile and substrate participate in the rate determining step.

The bulky base like LDA always abstracts the proton from the side of less substituted $\text{C}-\text{atom}$. The strong base, ${\text{NaOCH}}_{\text{3}}$ which is present in protic solvent like ${\text{CH}}_{\text{3}}\text{OH}$ always favors the elimination of the proton from the side of more substituted $\text{C}-\text{atom}$.

Answer to Problem 23.9P

The enolates that are formed by the reaction of the given ketone with LDA present in the THF solution and with ${\text{NaOCH}}_{\text{3}}$ present in ${\text{CH}}_{\text{3}}\text{OH}$ solution are shown below:

Explanation of Solution

The enolate that is formed by the reaction of the given ketone with LDA present in the THF solution is shown is shown as,

Figure 5

In this reaction, the given ketone is treated with LDA in the presence of THF solution to from an enolate ion. The strong base, LDA abstracts a proton from the less substituted carbon atom of the compound.

The enolate that is formed by the reaction of the given ketone with ${\text{NaOCH}}_{\text{3}}$ present in ${\text{CH}}_{\text{3}}\text{OH}$ solution is shown is shown as,

Figure 6

In this reaction, the given ketone is treated with ${\text{NaOCH}}_{\text{3}}$ present in ${\text{CH}}_{\text{3}}\text{OH}$ solution to from an enolate ion. The strong base, ${\text{NaOCH}}_{\text{3}}$ abstracts a proton from the more substituted carbon atom of the compound.

Conclusion

The enolates that are formed by the reaction of the given ketone with LDA present in the THF solution and with ${\text{NaOCH}}_{\text{3}}$ present in ${\text{CH}}_{\text{3}}\text{OH}$ solution are shown in Figure 5 and Figure 6.