Chapter 21, Problem 21.32AP

Interpretation Introduction

(a)

Interpretation:

The product obtained from the reaction of ethyl benzoate and ${\text{H}}_{\text{2}}\text{O}$ in presence of heat and acid catalyst is to be stated.

Concept introduction:

An ester is a derivative of carboxylic which is obtained by replacing the $-\text{OH}$ group with $-\text{OR}$ group where $\text{R}$ is any hydrocarbon chain. It is represented by the formula $\text{RCOOR}$. An ester is formed by the reaction of carboxylic with alcohol in the presence of an acid catalyst. This reaction is known as Fischer Esterification. The reverse of esterification reaction is known as acidic hydrolysis. When ester undergoes hydrolysis in the base, it is known as saponification.

Answer to Problem 21.32AP

The product obtained from the reaction of ethyl benzoate and ${\text{H}}_{\text{2}}\text{O}$ in presence of heat and acid catalyst is shown below.

Explanation of Solution

The reaction of ethyl benzoate in presence ${\text{H}}_{\text{2}}\text{O}$ in presence of heat and acid catalyst undergoes acid catalysis of ester. It results in the formation of benzoic acid and ethanol. The reaction is shown below.

Figure 1

Conclusion

The product obtained from the reaction of ethyl benzoate and ${\text{H}}_{\text{2}}\text{O}$ in presence of heat and acid catalyst is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation:

The product obtained from the reaction of ethyl benzoate and $\text{NaOH}$, ${\text{H}}_{\text{2}}\text{O}$ solvent is to be stated.

Concept introduction:

An ester is a derivative of carboxylic which is obtained by replacing the $-\text{OH}$ group with $-\text{OR}$ group where $\text{R}$ is any hydrocarbon chain. It is represented by the formula $\text{RCOOR}$. An ester is formed by the reaction of carboxylic with alcohol in the presence of an acid catalyst. This reaction is known as Fischer Esterification. The reverse of esterification reaction is known as acidic hydrolysis. When ester undergoes hydrolysis in the base, it is known as saponification.

Answer to Problem 21.32AP

The product obtained from the reaction of ethyl benzoate and $\text{NaOH}$, ${\text{H}}_{\text{2}}\text{O}$ solvent is shown below.

Explanation of Solution

The reaction of ethyl benzoate in the presence of $\text{NaOH}$, ${\text{H}}_{\text{2}}\text{O}$ solvent undergoes basic hydrolysis or saponification. It results in the formation of sodium salt of benzoic acid and ethanol. The reaction is shown below.

Figure 2

Conclusion

The product obtained from the reaction of ethyl benzoate and $\text{NaOH}$, ${\text{H}}_{\text{2}}\text{O}$ solvent is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation:

The product obtained from the reaction of ethyl benzoate and aqueous ${\text{NH}}_{\text{3}}$ in presence of heat is to be stated.

Concept introduction:

An ester is a derivative of carboxylic which is obtained by replacing the $-\text{OH}$ group with $-\text{OR}$ group where $\text{R}$ is any hydrocarbon chain. It is represented by the formula $\text{RCOOR}$. An ester is formed by the reaction of carboxylic with alcohol in the presence of an acid catalyst. This reaction is known as Fischer Esterification. The reverse of esterification reaction is known as acidic hydrolysis. When ester undergoes hydrolysis in the base, it is known as saponification.

Answer to Problem 21.32AP

The product obtained from the reaction of ethyl benzoate and aqueous ${\text{NH}}_{\text{3}}$ in presence of heat is shown below.

Explanation of Solution

The reaction of ethyl benzoate in the presence of aqueous ${\text{NH}}_{\text{3}}$ in presence of heat results in the formation of benzamide and ethanol. The reaction is shown below.

Figure 3

Conclusion

The product obtained from the reaction of ethyl benzoate and aqueous ${\text{NH}}_{\text{3}}$ in presence of heat is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation:

The product obtained from the reaction of ethyl benzoate and ${\text{LiAlH}}_{\text{4}}$ then ${\text{H}}_{\text{2}}\text{O}$ is to be stated.

Concept introduction:

An ester is a derivative of carboxylic which is obtained by replacing the $-\text{OH}$ group with $-\text{OR}$ group where $\text{R}$ is any hydrocarbon chain. It is represented by the formula $\text{RCOOR}$. An ester is formed by the reaction of carboxylic with alcohol in the presence of an acid catalyst. This reaction is known as Fischer Esterification. The reverse of esterification reaction is known as acidic hydrolysis. When ester undergoes hydrolysis in the base, it is known as saponification.

Answer to Problem 21.32AP

The product obtained from the reaction of ethyl benzoate and ${\text{LiAlH}}_{\text{4}}$ then ${\text{H}}_{\text{2}}\text{O}$ is shown below.

Explanation of Solution

The reduction reaction of ethyl benzoate takes place in the presence of ${\text{LiAlH}}_{\text{4}}$ then ${\text{H}}_{\text{2}}\text{O}$ followed by an acidic workup. It results in the formation of bezyl alcohol and ethanol. The reaction is shown below.

Figure 4

Conclusion

The product obtained from the reaction of ethyl benzoate and ${\text{LiAlH}}_{\text{4}}$ then ${\text{H}}_{\text{2}}\text{O}$ is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation:

The product obtained from the reaction of ethyl benzoate and excess ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$, then ${\text{H}}_{\text{2}}\text{O}$ is to be stated.

Concept introduction:

An ester is a derivative of carboxylic which is obtained by replacing the $-\text{OH}$ group with $-\text{OR}$ group where $\text{R}$ is any hydrocarbon chain. It is represented by the formula $\text{RCOOR}$. An ester is formed by the reaction of carboxylic with alcohol in the presence of an acid catalyst. This reaction is known as Fischer Esterification. The reverse of esterification reaction is known as acidic hydrolysis. When ester undergoes hydrolysis in the base, it is known as saponification.

Answer to Problem 21.32AP

The product obtained from the reaction of ethyl benzoate and excess ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ then ${\text{H}}_{\text{2}}\text{O}$ is shown below.

Explanation of Solution

The reaction of ethyl benzoate with an excess of Grignard reagent ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ followed by hydrolysis reaction. It results in the formation of $4-\text{phenylheptan}-4-\text{ol}$. The reaction is shown below.

Figure 5

Conclusion

The product obtained from the reaction of ethyl benzoate and excess ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$, then ${\text{H}}_{\text{2}}\text{O}$ is shown in Figure 5.

Interpretation Introduction

(f)

Interpretation:

The product obtained from the reaction of the product of part (e) and acetyl chloride, pyridine at $0\text{°C}$ is to be stated.

Concept introduction:

An ester is a derivative of carboxylic which is obtained by replacing the $-\text{OH}$ group with $-\text{OR}$ group where $\text{R}$ is any hydrocarbon chain. It is represented by the formula $\text{RCOOR}$. An ester is formed by the reaction of carboxylic with alcohol in the presence of an acid catalyst. This reaction is known as Fischer Esterification. The reverse of esterification reaction is known as acidic hydrolysis. When ester undergoes hydrolysis in the base, it is known as saponification.

Answer to Problem 21.32AP

The product obtained from the reaction of the product of part (e) and acetyl chloride, pyridine, at $0\text{°C}$ is shown below.

Explanation of Solution

The reaction of the product of part (e) and acetyl chloride, pyridine at $0\text{°C}$ undergoes substitution reaction. t results in the formation of an ester $4-\text{phenylheptan}-4-\text{yl}\text{acetate}$. The reaction is shown below.

Figure 6

Conclusion

The product obtained from the reaction of the product of part (e) and acetyl chloride, pyridine, at $0\text{°C}$ is shown in Figure 6.

Interpretation Introduction

(g)

Interpretation:

The product obtained from the reaction of the product of part (e) and benzenesulfonyl chloride is to be stated.

Concept introduction:

An ester is a derivative of carboxylic which is obtained by replacing the $-\text{OH}$ group with $-\text{OR}$ group where $\text{R}$ is any hydrocarbon chain. It is represented by the formula $\text{RCOOR}$. An ester is formed by the reaction of carboxylic with alcohol in the presence of an acid catalyst. This reaction is known as Fischer Esterification. The reverse of esterification reaction is known as acidic hydrolysis. When ester undergoes hydrolysis in the base, it is known as saponification.

Answer to Problem 21.32AP

The product obtained from the reaction of the product of part (e) and benzenesulfonyl chloride is shown below.

Explanation of Solution

The reaction of the product of part (e) and benzenesulphonyl chloride undergoes substitution reaction. It results in the formation of $4-\text{phenylheptan}-4-\text{yl}\text{benzenesulfonate}$. The reaction is shown below.

Figure 7

Conclusion

The product obtained from the reaction of the product of part (e) and benzenesulfonyl chloride is shown in Figure 7.

Interpretation Introduction

(h)

Interpretation:

The product obtained from the reaction of ethyl benzoate and ${\text{Na}}^{+}{\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{O}}^{-}$ is to be stated.

Concept introduction:

An ester is a derivative of carboxylic which is obtained by replacing the $-\text{OH}$ group with $-\text{OR}$ group where $\text{R}$ is any hydrocarbon chain. It is represented by the formula $\text{RCOOR}$. An ester is formed by the reaction of carboxylic with alcohol in the presence of an acid catalyst. This reaction is known as Fischer Esterification. The reverse of esterification reaction is known as acidic hydrolysis. When ester undergoes hydrolysis in the base, it is known as saponification.

Answer to Problem 21.32AP

The product obtained from the reaction of ethyl benzoate and ${\text{Na}}^{+}{\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{O}}^{-}$ is shown below.

Explanation of Solution

The reaction of ethyl benzoate with ${\text{Na}}^{+}{\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{O}}^{-}$ undergoes transesterification reaction. It results in the formation of a new ester. The reaction is shown below.

Figure 8

Conclusion

The product obtained from the reaction of ethyl benzoate and ${\text{Na}}^{+}{\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{O}}^{-}$ is shown in Figure 8.