Chapter 18, Problem 18.49P

For each N-substituted benzene, predict whether the compound reacts faster than, slower than, or at a similar rate to benzene in electrophilic aromatic substitution. Then draw the major product(s) formed when each compound reacts with a general electrophile ${\text{E}}^{+}$.

a. b. c. d.

Interpretation Introduction

(a)

Interpretation: The given compound reacts faster than, slower than, or at equal rate to benzene in electrophilic aromatic substitution is to be predicted and the major product(s) formed by the reaction between given compound and general electrophile ${\text{E}}^{+}$ is to be drawn.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron deficient chemical species that contains positive charge are known as electrophile. In electrophilic aromatic substitution reaction, electrophile takes the position of hydrogen atom by attacking the electron rich carbon atom of benzene.

Answer to Problem 18.49P

The given compound reacts faster in electrophilic substitution reaction than benzene ring. The major product formed by the reaction between given compound and general electrophile ${\text{E}}^{+}$ is shown below:

Explanation of Solution

The electron donating groups or activating groups make benzene ring more electron rich, as a result the compound reacts faster in electrophilic substitution reaction than benzene ring. On the other hand, the electron withdrawing groups or deactivating groups make benzene ring less electron rich; as a result the compound reacts slower in electrophilic substitution reaction than benzene ring.

In the given compound, benzene ring is attached to $-{\text{NR}}_{\text{2}}$ group, which is a strong electron donating group. Therefore, the given compound reacts faster in electrophilic substitution reaction than benzene ring.

The activating groups are ortho, para directing whereas the deactivating groups are meta directing. The major product formed by the reaction between given compound and general electrophile ${\text{E}}^{+}$ is shown in Figure 1.

Figure 1

Conclusion

The given compound reacts faster in electrophilic substitution reaction than benzene ring. The major product formed by the reaction between given compound and general electrophile ${\text{E}}^{+}$ is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: The given compound reacts faster than, slower than, or at equal rate to benzene in electrophilic aromatic substitution is to be predicted and the major product(s) formed by the reaction between given compound and general electrophile ${\text{E}}^{+}$ is to be drawn.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron deficient chemical species that contains positive charge are known as electrophile. In electrophilic aromatic substitution reaction, electrophile takes the position of hydrogen atom by attacking the electron rich carbon atom of benzene.

Answer to Problem 18.49P

The given compound reacts slower in electrophilic substitution reaction than benzene ring. The major product formed by the reaction between given compound and general electrophile ${\text{E}}^{+}$ is shown below:

Explanation of Solution

The electron donating groups or activating groups make benzene ring more electron rich, as a result the compound reacts faster in electrophilic substitution reaction than benzene ring. On the other hand, the electron withdrawing groups or deactivating groups make benzene ring less electron rich; as a result the compound reacts slower in electrophilic substitution reaction than benzene ring.

In the given compound, benzene ring is attached to $-\stackrel{+}{\text{N}}\text{H}{\left({\text{CH}}_3\right)}_{\text{2}}$ group, which is a strong electron withdrawing group. Therefore, the given compound reacts slower in electrophilic substitution reaction than benzene ring.

The activating groups are ortho, para directing whereas the deactivating groups are meta directing. The major product formed by the reaction between given compound and general electrophile ${\text{E}}^{+}$ is shown in Figure 2.

Figure 2

Conclusion

The given compound reacts slower in electrophilic substitution reaction than benzene ring. The major product formed by the reaction between given compound and general electrophile ${\text{E}}^{+}$ is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation: The given compound reacts faster than, slower than, or at equal rate to benzene in electrophilic aromatic substitution is to be predicted and the major product(s) formed by the reaction between given compound and general electrophile ${\text{E}}^{+}$ is to be drawn.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron deficient chemical species that contains positive charge are known as electrophile. In electrophilic aromatic substitution reaction, electrophile takes the position of hydrogen atom by attacking the electron rich carbon atom of benzene.

Answer to Problem 18.49P

The given compound reacts slower in electrophilic substitution reaction than benzene ring. The major product formed by the reaction between given compound and general electrophile ${\text{E}}^{+}$ is shown below:

Explanation of Solution

The electron donating groups or activating groups make benzene ring more electron rich, as a result the compound reacts faster in electrophilic substitution reaction than benzene ring. On the other hand, the electron withdrawing groups or deactivating groups make benzene ring less electron rich; as a result the compound reacts slower in electrophilic substitution reaction than benzene ring.

In the given compound, benzene ring is attached to $-{\text{NO}}_{\text{2}}$ and $-\stackrel{+}{\text{N}}{\left({\text{CH}}_{\text{3}}\right)}_{\text{3}}$ groups. Both of these groups are strong electron withdrawing group. Therefore, the given compound reacts slower in electrophilic substitution reaction than benzene ring.

The activating groups are ortho, para directing whereas the deactivating groups are meta directing. The major product formed by the reaction between given compound and general electrophile ${\text{E}}^{+}$ is shown in Figure 3.

Figure 3

Conclusion

The given compound reacts slower in electrophilic substitution reaction than benzene ring. The major product formed by the reaction between given compound and general electrophile ${\text{E}}^{+}$ is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation: The given compound reacts faster than, slower than, or at equal rate to benzene in electrophilic aromatic substitution is to be predicted and the major product(s) formed by the reaction between given compound and general electrophile ${\text{E}}^{+}$ is to be drawn.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron deficient chemical species that contains positive charge are known as electrophile. In electrophilic aromatic substitution reaction, electrophile takes the position of hydrogen atom by attacking the electron rich carbon atom of benzene.

Answer to Problem 18.49P

The given compound reacts at a similar rate to benzene in electrophilic substitution reaction. The major product formed by the reaction between given compound and general electrophile ${\text{E}}^{+}$ is shown below:

Explanation of Solution

The electron donating groups or activating groups make benzene ring more electron rich, as a result the compound reacts faster in electrophilic substitution reaction than benzene ring. On the other hand, the electron withdrawing groups or deactivating groups make benzene ring less electron rich; as a result the compound reacts slower in electrophilic substitution reaction than benzene ring.

In the given compound, benzene ring is attached to $-{\text{NR}}_{\text{2}}$ and $-{\text{NO}}_{\text{2}}$ groups. The $-{\text{NO}}_{\text{2}}$ group is a strong electron withdrawing group and $-{\text{NR}}_{\text{2}}$ group is a strong electron donating group. Therefore, the given compound reacts at a similar rate to benzene in electrophilic substitution reaction.

The activating groups are ortho, para directing whereas the deactivating groups are meta directing. The major product formed by the reaction between given compound and general electrophile ${\text{E}}^{+}$ is shown in Figure 4.

Figure 4

Conclusion

The given compound reacts at a similar rate to benzene in electrophilic substitution reaction. The major product formed by the reaction between given compound and general electrophile ${\text{E}}^{+}$ is shown in Figure 4.