Chapter 21, Problem 21.33AP

Interpretation Introduction

(a)

Interpretation:

The major product of the reaction between propionyl chloride and ${\text{H}}_{\text{2}}\text{O}$ is to be predicated.

Concept introduction:

Acid chloride is a acid of carboxylic acid derivatives. The general formula of acid chloride is $\text{RCOCl}$. The compound contains a carbonyl group attached to electronegative chloride atom. The electrophillic character of carbonyl carbon atom of acid chloride is high.

Answer to Problem 21.33AP

The major product of the reaction between propionyl chloride and ${\text{H}}_{\text{2}}\text{O}$ is shown below.

Explanation of Solution

Propionyl chloride undergoes hydrolysis reaction to from propionic acid. The water molecule acts as a nucleophile and attacks on the carbonyl carbon atom of propionyl chloride. The resultant compound lose $\text{HCl}$ molecule to form propionic acid.

The corresponding chemical reaction is shown below.

Figure 1

Conclusion

The major product of the reaction between propionyl chloride and ${\text{H}}_{\text{2}}\text{O}$ is in Figure 1.

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction between propionyl chloride, ethanethiol, and pyridine, at $0°\text{C}$ is to be predicated.

Concept introduction:

Acid chloride is a type of carboxylic acid derivatives. The general formula of acid chloride is $\text{RCOCl}$. The compound contains a carbonyl group attached to electronegative chloride atom. The electrophillic character of carbonyl carbon atom of acid chloride is high.

Answer to Problem 21.33AP

The major product of the reaction between propionyl chloride, ethanethiol, and pyridine, at $0°\text{C}$ is shown below.

Explanation of Solution

Propionyl chloride is a acyl chloride. It has a electrophilic carbonyl carbonyl carbon atom. The ethanethiol molecule acts as a nucleophile and attacks on the carbonyl carbon atom of propionyl chloride. The resultant compound lose $\text{HCl}$ molecule to form final compound.

The corresponding chemical reaction is shown below.

Figure 2

Conclusion

The major product of the reaction between propionyl chloride, ethanethiol, and pyridine, at $0°\text{C}$ is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation:

The major product of the reaction between propionyl chloride, ${\left({\text{CH}}_{\text{3}}\right)}_{\text{3}}\text{COH}$, and pyridine is to be predicated.

Concept introduction:

Acid chloride is a type of carboxylic acid derivatives. The general formula of acid chloride is $\text{RCOCl}$. The compound contains a carbonyl group attached to electronegative chloride atom. The electrophillic character of carbonyl carbon atom of acid chloride is high.

Answer to Problem 21.33AP

The major product of the reaction between propionyl chloride, ${\left({\text{CH}}_{\text{3}}\right)}_{\text{3}}\text{COH}$, and pyridine is shown below.

Explanation of Solution

Propionyl chloride is an acyl chloride. It has an electrophilic carbonyl carbon atom. The compound ${\left({\text{CH}}_{\text{3}}\right)}_{\text{3}}\text{COH}$ acts as a nucleophile and attacks on the carbonyl carbon atom of propionyl chloride. The resultant compound lose $\text{HCl}$ molecule to form final compound.

The corresponding chemical reaction is shown below.

Figure 3

Conclusion

The major product of the reaction between propionyl chloride, ${\left({\text{CH}}_{\text{3}}\right)}_{\text{3}}\text{COH}$, and pyridine is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation:

The major product of the reaction between propionyl chloride and ${\left({\text{CH}}_{\text{3}}\right)}_2\text{CuLi}$ at $-78°\text{C}$, then with ${\text{H}}_{\text{2}}\text{O}$ is to be predicated.

Concept introduction:

Acid chloride is a type of carboxylic acid derivatives. The general formula of acid chloride is $\text{RCOCl}$. The compound contains a carbonyl group attached to electronegative chloride atom. The electrophillic character of carbonyl carbon atom of acid chloride is high.

Answer to Problem 21.33AP

The major product of the reaction between propionyl chloride and ${\left({\text{CH}}_{\text{3}}\right)}_2\text{CuLi}$ at $-78°\text{C}$, then with ${\text{H}}_{\text{2}}\text{O}$ is shown below.

Explanation of Solution

Propionyl chloride is an acyl chloride. It has an electrophilic carbonyl carbon atom. The compound ${\left({\text{CH}}_{\text{3}}\right)}_2\text{CuLi}$ reacts with propionyl chloride at $-78°\text{C}$ followup by hydrolysis to from a ketone. The alkyl part of ${\left({\text{CH}}_{\text{3}}\right)}_2\text{CuLi}$ substitutes the chloro group of acyl chloride.

The corresponding chemical reaction is shown below.

Figure 4

Conclusion

The major product of the reaction between propionyl chloride and ${\left({\text{CH}}_{\text{3}}\right)}_2\text{CuLi}$ at $-78°\text{C}$, then with ${\text{H}}_{\text{2}}\text{O}$ is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation:

The major product of the reaction between propionyl chloride and ${\text{H}}_{\text{2}}$, $\text{Pd}$ catalyst (quinolinesulfur poison) is to be predicated.

Concept introduction:

Acid chloride is a type of carboxylic acid derivatives. The general formula of acid chloride is $\text{RCOCl}$. The compound contains a carbonyl group attached to electronegative chloride atom. The electrophillic character of carbonyl carbon atom of acid chloride is high.

Answer to Problem 21.33AP

The major product of the reaction between propionyl chloride and ${\text{H}}_{\text{2}}$, $\text{Pd}$ catalyst (quinolinesulfur poison) is shown below.

Explanation of Solution

Propionyl chloride is an acyl chloride. It has an electrophilic carbonyl carbon atom. propionyl chloride reduces similary as carbonylic acid with ${\text{H}}_{\text{2}}$, $\text{Pd}$ catalyst in the presence of quinolinesulfur poison to an aldehyde. The corresponding chemical reaction is shown below.

Figure 5

Conclusion

The major product of the reaction between propionyl chloride and ${\text{H}}_{\text{2}}$, $\text{Pd}$ catalyst (quinolinesulfur poison) is shown in Figure 5

Interpretation Introduction

(f)

Interpretation:

The major product of the reaction between propionyl chloride and ${\text{AlCl}}_3$, toluene, then with ${\text{H}}_{\text{2}}\text{O}$ is to be predicated.

Concept introduction:

Acid chloride is a type of carboxylic acid derivatives. The general formula of acid chloride is $\text{RCOCl}$. The compound contains a carbonyl group attached to electronegative chloride atom. The electrophillic character of carbonyl carbon atom of acid chloride is high.

Answer to Problem 21.33AP

The major product of the reaction between propionyl chloride and ${\text{AlCl}}_3$, toluene, then with ${\text{H}}_{\text{2}}\text{O}$ is shown below.

Explanation of Solution

Propionyl chloride is an acyl chloride. It has an electrophilic carbonyl carbon atom. The compound undergoes Fredal craft acylation reaction with toluene in the presence of catalyst ${\text{AlCl}}_3$ to from an acylated aromatic compound.

The corresponding chemical reaction is shown below.

Figure 6

Conclusion

The major product of the reaction between propionyl chloride and ${\text{AlCl}}_3$, toluene, then with ${\text{H}}_{\text{2}}\text{O}$ is shown in Figure 6.

Interpretation Introduction

(g)

Interpretation:

The major product of the reaction between propionyl chloride and ${\left({\text{CH}}_3\right)}_2{\text{CHNH}}_{\text{2}}\left(\text{2}\text{equiv}\text{.}\right)$ is to be predicated.

Concept introduction:

Acid chloride is a type of carboxylic acid derivatives. The general formula of acid chloride is $\text{RCOCl}$. The compound contains a carbonyl group attached to electronegative chloride atom. The electrophillic character of carbonyl carbon atom of acid chloride is high.

Answer to Problem 21.33AP

The major product of the reaction between propionyl chloride and ${\left({\text{CH}}_3\right)}_2{\text{CHNH}}_{\text{2}}\left(\text{2}\text{equiv}\text{.}\right)$ is shown below.

Explanation of Solution

Propionyl chloride is an acyl chloride. It has an electrophilic carbonyl carbon atom. The compound ${\left({\text{CH}}_3\right)}_2{\text{CHNH}}_{\text{2}}$ acts as a nucleophile and attacks on the carbonyl carbon atom of propionyl chloride. Another molecule of ${\left({\text{CH}}_3\right)}_2{\text{CHNH}}_{\text{2}}$ reacts with the resultant compound to from an amide and ammonium chloride.

The corresponding chemical reaction is shown below.

Figure 7

Conclusion

The major product of the reaction between propionyl chloride and ${\left({\text{CH}}_3\right)}_2{\text{CHNH}}_{\text{2}}\left(\text{2}\text{equiv}\text{.}\right)$ is shown in Figure 7.

Interpretation Introduction

(h)

Interpretation:

The major product of the reaction between propionyl chloride and sodium benzoate is to be predicated.

Concept introduction:

Acid chloride is a type of carboxylic acid derivatives. The general formula of acid chloride is $\text{RCOCl}$. The compound contains a carbonyl group attached to electronegative chloride atom. The electrophillic character of carbonyl carbon atom of acid chloride is high.

Answer to Problem 21.33AP

The major product of the reaction between propionyl chloride and sodium benzoate is shown below.

Explanation of Solution

Propionyl chloride is an acyl chloride. It has an electrophilic carbonyl carbon atom. Th The compound sodium benzoate reacts with propionyl chloride. The resultant compound lose $\text{HCl}$ molecule to form final compound.

The corresponding chemical reaction is shown below.

Figure 8

Conclusion

The major product of the reaction between propionyl chloride and sodium benzoate is shown in Figure 8.

Interpretation Introduction

(i)

Interpretation:

The major product of the reaction between propionylchloride, $p-\text{cresol}\left(\text{4-methylphenol}\right)$, and pyridine is to be predicated.

Concept introduction:

Acid chloride is a type of carboxylic acid derivatives. The general formula of acid chloride is $\text{RCOCl}$. The compound contains a carbonyl group attached to electronegative chloride atom. The electrophillic character of carbonyl carbon atom of acid chloride is high.

Answer to Problem 21.33AP

The major product of the reaction between propionyl chloride, $p-\text{cresol}\left(\text{4-methylphenol}\right)$, and pyridine is shown below.

Explanation of Solution

Propionyl chloride is an acyl chloride. It has an electrophilic carbonyl carbon atom. Th The compound $p-\text{cresol}$ reacts with propionyl chloride in the presence of base pyridine. The resultant compound lose $\text{HCl}$ molecule to form final compound.

The corresponding chemical reaction is shown below.

Figure 9

Conclusion

The major product of the reaction between propionyl chloride, $p-\text{cresol}\left(\text{4-methylphenol}\right)$, and pyridine is shown in Figure 9.