Chapter 22, Problem 22.48P

Interpretation Introduction

(a)

Interpretation:

The product formed by the treatment of ethyl butanoate $\left[\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{COOCH}}_2{\text{CH}}_3\right)\right]$ with the given reagent is to be drawn.

Concept introduction:

The replacement or substitution of one functional group with another functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons is known as a nucleophile. In nucleophilic acyl substitution reaction, a nucleophile takes the position of a leaving group.

Answer to Problem 22.48P

No product is formed by the treatment of ethyl butanoate with ${\text{SOCl}}_{\text{2}}$.

Explanation of Solution

Esters do not undergo reaction with ${\text{SOCl}}_{\text{2}}$. The replacement of ${\text{RCOO}}^{-}$ group of acid anhydride with $\text{Cl}$ atom does not take place because ${\text{RCOO}}^{-}$ is a poor leaving group. Therefore, no product is formed by the treatment of ethyl butanoate with ${\text{SOCl}}_{\text{2}}$ as shown below.

Figure 1

Conclusion

No product is formed by the treatment of ethyl butanoate with ${\text{SOCl}}_{\text{2}}$.

Interpretation Introduction

(b)

Interpretation:

The product formed by the treatment of ethyl butanoate $\left[\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{COOCH}}_2{\text{CH}}_3\right)\right]$ with the given reagent is to be drawn.

Concept introduction:

The replacement or substitution of one functional group with another functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons is known as a nucleophile. In nucleophilic acyl substitution reaction, a nucleophile takes the position of a leaving group.

Answer to Problem 22.48P

The product formed by the treatment of ethyl butanoate $\left[\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{COOCH}}_2{\text{CH}}_3\right)\right]$ with the given reagent is,

Explanation of Solution

Esters undergo hydrolysis under acidic and basic medium. In the given reaction, ester undergoes hydrolysis under acidic medium. One mole of carboxylic acid and one mole of alcohol are produced from the hydrolysis of ethyl butanoate as shown in Figure 2.

Figure 2

Conclusion

The product formed by the treatment of ethyl butanoate $\left[\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{COOCH}}_2{\text{CH}}_3\right)\right]$ with the given reagent is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation:

The product formed by the treatment of ethyl butanoate $\left[\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{COOCH}}_2{\text{CH}}_3\right)\right]$ with the given reagent is to be drawn.

Concept introduction:

The replacement or substitution of one functional group with another functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons is known as a nucleophile. In nucleophilic acyl substitution reaction, a nucleophile takes the position of a leaving group.

Answer to Problem 22.48P

The product formed by the treatment of ethyl butanoate $\left[\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{COOCH}}_2{\text{CH}}_3\right)\right]$ with the given reagent is,

Explanation of Solution

Esters undergo hydrolysis under acidic and basic medium. In the given reaction, ester undergoes hydrolysis under basic medium. One mole of carboxylate ion and one mole of alcohol are produced from the hydrolysis of ethyl butanoate as shown in Figure 3.

Figure 3

Conclusion

The product formed by the treatment of ethyl butanoate $\left[\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{COOCH}}_2{\text{CH}}_3\right)\right]$ with the given reagent is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation:

The product formed by the treatment of ethyl butanoate $\left[\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{COOCH}}_2{\text{CH}}_3\right)\right]$ with the given reagent is to be drawn.

Concept introduction:

The replacement or substitution of one functional group with another functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons is known as a nucleophile. In nucleophilic acyl substitution reaction, a nucleophile takes the position of a leaving group.

Answer to Problem 22.48P

The product formed by the treatment of ethyl butanoate $\left[\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{COOCH}}_2{\text{CH}}_3\right)\right]$ with the given reagent is,

Explanation of Solution

The reaction of ester with ammonia leads to the formation of amide and alcohol. The nitrogen atom of ammonia contains lone pair of electrons. The nitrogen atom acts as a nucleophile and attacks on the electron deficient carbonyl carbon atom of ester. The products formed by the reaction of ethyl butanoate with ${\text{NH}}_{\text{3}}$ are shown below.

Figure 4

Conclusion

The product formed by the treatment of ethyl butanoate $\left[\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{COOCH}}_2{\text{CH}}_3\right)\right]$ with the given reagent is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation:

The product formed by the treatment of ethyl butanoate $\left[\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{COOCH}}_2{\text{CH}}_3\right)\right]$ with the given reagent is to be drawn.

Concept introduction:

The replacement or substitution of one functional group with another functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons is known as a nucleophile. In nucleophilic acyl substitution reaction, a nucleophile takes the position of a leaving group.

Answer to Problem 22.48P

The product formed by the treatment of ethyl butanoate $\left[\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{COOCH}}_2{\text{CH}}_3\right)\right]$ with the given reagent is,

Explanation of Solution

The reaction of ester with primary amine leads to the formation of amide. The nitrogen atom of ${\text{CH}}_3{\text{CH}}_2{\text{NH}}_2$ contains lone pair of electrons. The nitrogen atom acts as a nucleophile and attack on the electron deficient carbonyl carbon atom. The reaction between ethyl butanoate and ${\text{CH}}_3{\text{CH}}_2{\text{NH}}_2$ is show in Figure 5.

Figure 5

Conclusion

The product formed by the treatment of ethyl butanoate $\left[\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{COOCH}}_2{\text{CH}}_3\right)\right]$ with the given reagent is shown in Figure 5.