Chapter 23, Problem 23.49P

Interpretation Introduction

(a)

Interpretation: The products formed by the reaction of ${\text{Na}}^{+}{}^{-}\text{CH}{\left({\text{CO}}_{\text{2}}\text{Et}\right)}_2$ with the given electrophile followed by treatment with ${\text{H}}_{\text{2}}\text{O}$ are to be drawn.

Concept introduction: Nucleophilic addition reaction is a type of organic reaction in which the nucleophile is added to the electrophilic site. The carbon atom in carbonyl compound acts as an electrophilic centre where a nucleophile attacks and gives an addition product.

Answer to Problem 23.49P

The product formed by the reaction of ${\text{Na}}^{+}{}^{-}\text{CH}{\left({\text{CO}}_{\text{2}}\text{Et}\right)}_2$ with given electrophile followed by treatment with ${\text{H}}_{\text{2}}\text{O}$ is $\text{diethyl 2-}\left(\text{2-hydroxypropyl}\right)\text{malonate}$.

Explanation of Solution

The given compound is,

Figure 1

The nucleophile ${}^{-}\text{CH}{\left({\text{CO}}_{\text{2}}\text{Et}\right)}_2$ attacks on the electrophilic centre of the given compound and forms a product followed by hydrolysis. The final product is $\text{diethyl 2-}\left(\text{2-hydroxypropyl}\right)\text{malonate}$. The reaction is shown below.

Figure 2

On the further treatment of $\text{diethyl 2-}\left(\text{2-hydroxypropyl}\right)\text{malonate}$ with water in the presence of heat, it forms derivative of carboxylic acid. The reaction is shown below.

Figure 3

Hence, the product formed by the reaction of ${\text{Na}}^{+}{}^{-}\text{CH}{\left({\text{CO}}_{\text{2}}\text{Et}\right)}_2$ with given electrophile followed by treatment with ${\text{H}}_{\text{2}}\text{O}$ is $\text{diethyl 2-}\left(\text{2-hydroxypropyl}\right)\text{malonate}$. On further treatment of product with water in the presence of heat yields the derivative of carboxylic acid.

Conclusion

The product formed by the reaction of ${\text{Na}}^{+}{}^{-}\text{CH}{\left({\text{CO}}_{\text{2}}\text{Et}\right)}_2$ with given electrophile followed by treatment with ${\text{H}}_{\text{2}}\text{O}$ is $\text{diethyl 2-}\left(\text{2-hydroxypropyl}\right)\text{malonate}$.

Interpretation Introduction

(b)

Interpretation: The products formed by the reaction of ${\text{Na}}^{+}{}^{-}\text{CH}{\left({\text{CO}}_{\text{2}}\text{Et}\right)}_2$ with given electrophile followed by treatment with ${\text{H}}_{\text{2}}\text{O}$ are to be drawn.

Concept introduction: Nucleophilic addition reaction is a type of organic reaction in which the nucleophile is added to the electrophilic site. The carbon atom in carbonyl compound acts as an electrophilic centre where a nucleophile attacks and gives an addition product.

Answer to Problem 23.49P

The product formed by the reaction of ${\text{Na}}^{+}{}^{-}\text{CH}{\left({\text{CO}}_{\text{2}}\text{Et}\right)}_2$ with given electrophile followed by treatment with ${\text{H}}_{\text{2}}\text{O}$ is $\text{diethyl 2-}\left(\text{hydroxymethyl}\right)\text{malonate}$. On the further treatment of product with water in the presence of heat yields the derivative of carboxylic acid.

Explanation of Solution

The given compound is,

Figure 4

The nucleophile ${}^{-}\text{CH}{\left({\text{CO}}_{\text{2}}\text{Et}\right)}_2$ attacks on the electrophilic centre of the given compound and forms a product followed by hydrolysis. The final product is $\text{diethyl 2-}\left(\text{hydroxymethyl}\right)\text{malonate}$. The reaction is shown below.

Figure 5

On the further treatment of $\text{diethyl 2-}\left(\text{hydroxymethyl}\right)\text{malonate}$ with water in the presence of heat, it forms derivative of carboxylic acid. The reaction is shown below.

Figure 6

Hence, the product formed by the reaction of ${\text{Na}}^{+}{}^{-}\text{CH}{\left({\text{CO}}_{\text{2}}\text{Et}\right)}_2$ with given electrophile followed by treatment with ${\text{H}}_{\text{2}}\text{O}$ is $\text{diethyl 2-}\left(\text{hydroxymethyl}\right)\text{malonate}$. On further treatment of product with water in the presence of heat yields derivative of carboxylic acid.

Conclusion

The product formed by the reaction of ${\text{Na}}^{+}{}^{-}\text{CH}{\left({\text{CO}}_{\text{2}}\text{Et}\right)}_2$ with given electrophile followed by treatment with ${\text{H}}_{\text{2}}\text{O}$ is $\text{diethyl 2-}\left(\text{hydroxymethyl}\right)\text{malonate}$.

Interpretation Introduction

(c)

Interpretation: The products formed by the reaction of ${\text{Na}}^{+}{}^{-}\text{CH}{\left({\text{CO}}_{\text{2}}\text{Et}\right)}_2$ with given electrophile followed by treatment with ${\text{H}}_{\text{2}}\text{O}$ are to be drawn.

Concept introduction: Nucleophilic addition reaction is a type of organic reaction in which the nucleophile is added to the electrophilic site. The carbon atom in carbonyl compound acts as an electrophilic centre where a nucleophile attacks and gives an addition product.

Answer to Problem 23.49P

The product formed by the reaction of ${\text{Na}}^{+}{}^{-}\text{CH}{\left({\text{CO}}_{\text{2}}\text{Et}\right)}_2$ with given electrophile followed by treatment with ${\text{H}}_{\text{2}}\text{O}$ is $\text{diethyl 2-acetylmalonate}$. On further treatment of product with water in the presence of heat yields the derivative of carboxylic acid.

Explanation of Solution

The given compound is,

Figure 7

The nucleophile ${}^{-}\text{CH}{\left({\text{CO}}_{\text{2}}\text{Et}\right)}_2$ attacks on the electrophilic centre of the given compound and forms a product followed by hydrolysis. The final product is $\text{diethyl 2-acetylmalonate}$. The reaction is shown below.

Figure 8

On the further treatment of $\text{diethyl 2-acetylmalonate}$ with water in the presence of heat, it forms derivative of carboxylic acid. The reaction is shown below.

Figure 9

Hence, the product formed by the reaction of ${\text{Na}}^{+}{}^{-}\text{CH}{\left({\text{CO}}_{\text{2}}\text{Et}\right)}_2$ with given electrophile followed by treatment with ${\text{H}}_{\text{2}}\text{O}$ is $\text{diethyl 2-acetylmalonate}$. On further treatment of product with water in the presence of heat yields the derivative of carboxylic acid.

Conclusion

The product formed by the reaction of ${\text{Na}}^{+}{}^{-}\text{CH}{\left({\text{CO}}_{\text{2}}\text{Et}\right)}_2$ with given electrophile followed by treatment with ${\text{H}}_{\text{2}}\text{O}$ is $\text{diethyl 2-acetylmalonate}$.

Interpretation Introduction

(d)

Interpretation: The product formed by the reaction of ${\text{Na}}^{+}{}^{-}\text{CH}{\left({\text{CO}}_{\text{2}}\text{Et}\right)}_2$ with given electrophile followed by treatment with ${\text{H}}_{\text{2}}\text{O}$ is to be drawn.

Concept introduction: Nucleophilic addition reaction is a type of organic reaction in which the nucleophile is added to the electrophilic site. The carbon atom in carbonyl compound acts as an electrophilic centre where a nucleophile attacks and gives an addition product.

Answer to Problem 23.49P

The products formed by the reaction of ${\text{Na}}^{+}{}^{-}\text{CH}{\left({\text{CO}}_{\text{2}}\text{Et}\right)}_2$ with given electrophile followed by treatment with ${\text{H}}_{\text{2}}\text{O}$ are $\text{diethyl 2-acetylmalonate}$ and ethanoic acid. On further treatment of product with water in the presence of heat yields the derivative of carboxylic acid.

Explanation of Solution

The given compound is,

Figure 10

The nucleophile ${}^{-}\text{CH}{\left({\text{CO}}_{\text{2}}\text{Et}\right)}_2$ attacks on the electrophilic centre of the given compound and forms a product followed by hydrolysis. The final products are $\text{diethyl 2-acetylmalonate}$ and ethanoic acid. The reaction is shown below.

Figure 11

On the further treatment of $\text{diethyl 2-acetylmalonate}$ with water in the presence of heat, it forms derivative of carboxylic acid. The reaction is shown below.

Figure 12

Hence, the products formed by the reaction of ${\text{Na}}^{+}{}^{-}\text{CH}{\left({\text{CO}}_{\text{2}}\text{Et}\right)}_2$ with given electrophile followed by treatment with ${\text{H}}_{\text{2}}\text{O}$ are $\text{diethyl 2-acetylmalonate}$ and ethanoic acid. On further treatment of product with water in the presence of heat yields the derivative of carboxylic acid.

Conclusion

The products formed by the reaction of ${\text{Na}}^{+}{}^{-}\text{CH}{\left({\text{CO}}_{\text{2}}\text{Et}\right)}_2$ with given electrophile followed by treatment with ${\text{H}}_{\text{2}}\text{O}$ are $\text{diethyl 2-acetylmalonate}$ and ethanoic acid.