Chapter 21, Problem 21.36P

Interpretation Introduction

(a)

Interpretation:

The product of the reaction between $\text{m-ethylbenzoyl chloride}$ and ${\text{H}}_{\text{2}}\text{O}$ is to be predicted. The complete, detailed mechanism for the same reaction is to be drawn. If no reaction is expected to occur, “no reaction” is to be written.

Concept introduction:

The carbonyl carbon of the acid chloride is highly electrophilic and shows nucleophilic addition-elimination reaction with the nucleophile. In the first step, the nucleophile adds the electron deficient carbonyl carbon; it is known as the nucleophilic addition step. Since the chlorine atom is a good leaving group, it departs from the substrate in a nucleophilic elimination step.

Answer to Problem 21.36P

The product of the given reaction is

The complete detailed mechanism for the given reaction is

Explanation of Solution

The given reaction is

Since water is a nucleophile, it attacks the electron deficient carbonyl carbon of $\text{m-ethylbenzoyl chloride}$ and forces the bonding electron pair onto the oxygen atom in the first step. A negative charge will appear on the carbonyl oxygen.

In the second step, the positive charge of the water’s oxygen is deprotonated, and simultaneously the chlorine anoin departs from the substrate with its bonding pair. Thus, it is called a nucleophilic elimination.

Conclusion

The product of the reaction between $\text{m-ethylbenzoyl chloride}$ and ${\text{H}}_{\text{2}}\text{O}$ is predicted. The complete, detailed mechanism for the same reaction is drawn.

Interpretation Introduction

(b)

Interpretation:

The product of the reaction between $\text{m-ethylbenzoyl chloride}$ and ${\text{NH}}_{\text{2}}{\text{CH}}_{\text{3}}$ is to be predicted. The complete, detailed mechanism for the same reaction is to be drawn. If no reaction is expected to occur, “no reaction” is to be written.

Concept introduction:

The carbonyl carbon of the acid chloride is highly electrophilic and shows nucleophilic addition-elimination reaction with the nucleophile. In the first step, the nucleophile adds the electron deficient carbonyl carbon; it is known as the nucleophilic addition step. Since the chlorine atom is a good leaving group, it departs from the substrate in a nucleophilic elimination step.

Answer to Problem 21.36P

The product of the given reaction is

The complete detailed mechanism for the given reaction is

Explanation of Solution

The given reaction is

Since methyl amine (${\text{NH}}_{\text{2}}{\text{CH}}_{\text{3}}$) is a nucleophile, it attacks the electron deficient carbonyl carbon of $\text{m-ethylbenzoyl chloride}$ and forces the bonding electron pair onto the oxygen atom in the first step. A negative charge will appear on the carbonyl oxygen.

In the second step, the positive charge of the nitrogen atom is deprotonated, and simultaneously chlorine atom departs from the substrate with its bonding pair in a nucleophilic elimination step.

Conclusion

The product of the reaction between $\text{m-ethylbenzoyl chloride}$ and ${\text{NH}}_{\text{2}}{\text{CH}}_{\text{3}}$ is predicted. The complete, detailed mechanism for the same reaction is drawn.

Interpretation Introduction

(c)

Interpretation:

The product of the reaction between $\text{m-ethylbenzoyl chloride}$ and $\left(\text{S}\right)\text{-butan-2-ol}$ is to be predicted. The complete, detailed mechanism for the same reaction is to be drawn. If no reaction is expected to occur, “no reaction” is to be written.

Concept introduction:

The carbonyl carbon of the acid chloride is highly electrophilic and shows nucleophilic addition-elimination reaction with the nucleophile. In the first step, the nucleophile adds the electron deficient carbonyl carbon; it is known as the nucleophilic addition step. Since the chlorine atom is a good leaving group, it departs from the substrate in a nucleophilic elimination step.

Answer to Problem 21.36P

The product of the given reaction is

The complete detailed mechanism for the given reaction is

Explanation of Solution

The given reaction is

Since an alcohol is a nucleophile, it attacks the electron deficient carbonyl carbon of $\text{m-ethylbenzoyl chloride}$ and forces the bonding electron pair onto the oxygen atom in the first step. A negative charge will appear on the carbonyl oxygen.

In the second step, the positive charge of the alcohol’s oxygen is deprotonated, and simultaneously the chlorine anion departs from the substrate with its bonding pair. Thus, it is called a nucleophilic elimination.

Conclusion

The product of the reaction between $\text{m-ethylbenzoyl chloride}$ and $\left(\text{S}\right)\text{-butan-2-ol}$ is predicted. The complete, detailed mechanism for the same reaction is drawn.

Interpretation Introduction

(d)

Interpretation:

The product of the reaction between $\text{m-ethylbenzoyl chloride}$ and diethyl ether is to be predicted. The complete, detailed mechanism for the same reaction is to be drawn. If no reaction is expected to occur, “no reaction” is to be written.

Concept introduction:

The carbonyl carbon of the acid chloride is highly electrophilic and shows nucleophilic addition-elimination reaction with the nucleophile. In the first step, the nucleophile adds the electron deficient carbonyl carbon; it is known as the nucleophilic addition step. Since the chlorine atom is a good leaving group, it departs from the substrate in a nucleophilic elimination step.

Answer to Problem 21.36P

No reaction occurs as the positive charge of the oxygen atom is not simply deprotonated.

Explanation of Solution

The given reaction is

When the lone pair of the oxygen atom attacks the carbonyl carbon, it acquires a positive charge, which does not show deprotonation reaction.

Thus, the given reaction does not occur.

Conclusion

No reaction occurs as the positive charge of the oxygen atom is not simply deprotonated.