Chapter 22, Problem 22.45P

Draw the product formed when pentanoyl chloride $\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{COCl}\right)$ is treated with each reagent.

a. ${\text{H}}_{\text{2}}\text{O}$, pyridine c. ${\text{CH}}_{\text{3}}{\text{COO}}^{-}$ e. ${\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\right)}_{\text{2}}\text{NH}$ (excess)

b. ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{OH}$, pyridine d. ${\text{NH}}_{\text{3}}$ (excess) f. ${\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{NH}}_{\text{2}}$ (excess)

Interpretation Introduction

(a)

Interpretation:

The product formed by the treatment of pentanoyl chloride $\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{COCl}\right)$ 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 22.45P

The product formed by the treatment of pentanoyl chloride $\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{COCl}\right)$ with the given reagent is,

Explanation of Solution

Acyl chloride on reaction with ${\text{H}}_{\text{2}}\text{O}$ in the presence of pyridine converts into carboxylic acid. The chlorine group of acyl chloride is replaced by $\text{OH}$ group. In the given reaction, pentanoyl chloride converts into pentanoic acid as shown in Figure 1.

Figure 1

Conclusion

The product formed by the treatment of pentanoyl chloride $\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{COCl}\right)$ given reagent is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation:

The product formed by the treatment of pentanoyl chloride $\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{COCl}\right)$ 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 22.45P

The product formed by the treatment of pentanoyl chloride $\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{COCl}\right)$ with the given reagent is,

Explanation of Solution

The acyl chloride on reaction with alcohol converts into ester. The oxygen atom of alcoholic $\left(\text{OH}\right)$ group contains lone pair of electrons. It undergoes nucleophilic attack on electron deficient carbonyl carbon atom and replaces chlorine atom. The reaction between pentanoyl chloride and ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{OH}$ is show in Figure 2.

Figure 2

Conclusion

The product formed by the treatment of pentanoyl chloride $\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{COCl}\right)$ given reagent is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation:

The product formed by the treatment of pentanoyl chloride $\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{COCl}\right)$ 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 22.45P

The product formed by the treatment of pentanoyl chloride $\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{COCl}\right)$ with the given reagent is,

Explanation of Solution

The acyl chloride on reaction with acetate ion converts into acid anhydride. The oxygen atom of acetate ion contains negative charge. It undergoes nucleophilic attack on electron deficient carbonyl carbon atom and replaces chlorine atom. The reaction between pentanoyl chloride and ${\text{CH}}_{\text{3}}{\text{COO}}^{-}$ is shown in Figure 3.

Figure 3

Conclusion

The product formed by the treatment of pentanoyl chloride $\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{COCl}\right)$ given reagent is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation:

The product formed by the treatment of pentanoyl chloride $\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{COCl}\right)$ 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 22.45P

The product formed by the treatment of pentanoyl chloride $\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{COCl}\right)$ with the given reagent is,

Explanation of Solution

The reaction of acyl chloride with ammonia $\left({\text{NH}}_{\text{3}}\right)$ leads to the formation of amide. The nitrogen atom of ${\text{NH}}_{\text{3}}$ contains lone pair of electrons. The nitrogen atom acts as a nucleophile and attacks on the electron deficient carbonyl carbon atom. The reaction between pentanoyl chloride and ${\text{NH}}_3$ is shown in Figure 4.

Figure 4

Conclusion

The product formed by the treatment of pentanoyl chloride $\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{COCl}\right)$ given reagent is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation:

The product formed by the treatment of pentanoyl chloride $\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{COCl}\right)$ 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 22.45P

The product formed by the treatment of pentanoyl chloride $\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{COCl}\right)$ with the given reagent is,

Explanation of Solution

The reaction of acyl chloride with secondary amine leads to the formation of amide. The nitrogen atom of ${\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\right)}_{\text{2}}\text{NH}$ contains lone pair of electrons. The nitrogen atom acts as a nucleophile and attacks on the electron deficient carbonyl carbon atom. The reaction between pentanoyl chloride and ${\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\right)}_{\text{2}}\text{NH}$ is shown in Figure 5.

Figure 5

Conclusion

The product formed by the treatment of pentanoyl chloride $\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{COCl}\right)$ given reagent is shown in Figure 5.

Interpretation Introduction

(f)

Interpretation:

The product formed by the treatment of pentanoyl chloride $\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{COCl}\right)$ 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 22.45P

The product formed by the treatment of pentanoyl chloride $\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{COCl}\right)$ with the given reagent is,

Explanation of Solution

The reaction of acyl chloride with primary amine leads to the formation of amide. The nitrogen atom of ${\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{NH}}_2$ contains lone pair of electrons. The nitrogen atom acts as a nucleophile and attack on the electron deficient carbonyl carbon atom. The reaction between pentanoyl chloride and ${\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{NH}}_2$ is shown in Figure 6.

Figure 6

Conclusion

The product formed by the treatment of pentanoyl chloride $\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{COCl}\right)$ given reagent is shown in Figure 6.