Chapter 18, Problem 18.16P

Interpretation Introduction

(a)

Interpretation: The products formed when given compound is treated with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ are to be drawn. Whether the reaction occurs faster or slower than a similar reaction with benzene is to be stated.

Concept introduction: Benzene undergoes electrophile substitution. The kinetics of the electrophilic substitution reaction depends upon the nature of substituent present on the benzene ring. Electron releasing groups activates the ring towards the electrophilic substitution reaction while electron withdrawing groups deactivates the ring towards the electrophilic substitution reaction.

Answer to Problem 18.16P

The product formed by the reaction of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ is,

The reaction occurs slower because benzene ring contains deactivating group.

Explanation of Solution

Electron withdrawing groups deactivates the ring towards the electrophilic substitution reaction.

The substituent present in the given compound is electron withdrawing group. Thus, it directs the electrophile to meta position and deactivates the ring towards the electrophilic substitution reaction. Hence, the given compound reacts slower than benzene. The reaction is shown below.

Figure 1

Conclusion

The product formed by the reaction of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ is shown in Figure 1. The reaction occurs slower because benzene ring contains deactivating group.

Interpretation Introduction

(b)

Interpretation: The products formed when given compound is treated with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ are to be drawn. Whether the reaction occurs faster or slower than a similar reaction with benzene is to be stated.

Concept introduction: Benzene undergoes electrophile substitution. The kinetics of the electrophilic substitution reaction depends upon the nature of substituent present on the benzene ring. Electron releasing groups activates the ring towards the electrophilic substitution reaction while electron withdrawing groups deactivates the ring towards the electrophilic substitution reaction.

Answer to Problem 18.16P

The product formed by the reaction of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ is,

The reaction occurs slower because benzene ring contains deactivating group.

Explanation of Solution

Electron withdrawing groups deactivates the ring towards the electrophilic substitution reaction.

The substituent present in the given compound is electron withdrawing group. Thus it directs the electrophile to meta position and deactivates the ring towards the electrophilic substitution reaction. Hence, the given compound reacts slower than benzene. The reaction is shown below.

Figure 2

Conclusion

The product formed by the reaction of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ is shown in Figure 2. The reaction occurs slower because benzene ring contains deactivating group.

Interpretation Introduction

(c)

Interpretation: The products formed when given compound is treated with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$. is to be drawn. The reaction occurs faster or slower than a similar reaction with benzene is to be stated.

Concept introduction: Benzene undergoes electrophile substitution. The kinetics of the electrophile substitution reaction depends upon the nature of substituent present on the benzene ring. Electron releasing groups activates the ring towards the electrophilic substitution reaction while electron withdrawing groups deactivates the ring towards the electrophilic substitution reaction.

Answer to Problem 18.16P

The product formed by the reaction of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ are,

The reaction occurs faster because benzene ring contains activating group.

Explanation of Solution

Electron releasing group directs the electrophile to ortho and para position.

The substituent present in the given compound is electron donating group. Thus, it directs the electrophile to ortho and para position and activates the ring towards the electrophilic substitution reaction. Hence, the given compound reacts faster than benzene. The reaction is shown below.

Figure 3

Conclusion

The product formed by the reaction of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ is shown in Figure 3. The reaction occurs faster because benzene ring contains activating group.

Interpretation Introduction

(d)

Interpretation: The products formed when given compound is treated with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ is to be drawn. The reaction occurs faster or slower than a similar reaction with benzene is to be stated.

Concept introduction: Benzene undergoes electrophile substitution. The kinetics of the electrophilic substitution reaction depends upon the nature of substituent present on the benzene ring. Electron releasing groups activates the ring towards the electrophilic substitution reaction while electron withdrawing groups deactivates the ring towards the electrophilic substitution reaction.

Answer to Problem 18.16P

The products formed by the reaction of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ are,

The reaction occurs slower benzene ring because benzene ring contains deactivating group.

Explanation of Solution

The substituent present in the given compound is $\text{Cl}$. It contains lone pairs which participate in resonance as it shows mesomeric effect. The chlorine is more electronegative than carbon atom. It shows negative inductive effect.

Among these two cases, mesomeric effect predominates over inductive effect. Hence, chlorine on benzene ring acts as releasing group but deactivates the benzene ring due to its $-\text{I}$ effect.

Thus, it directs the electrophile to ortho and para position and deactivates the ring towards the electrophilic substitution reaction. Hence, the given compound reacts slower than benzene. The reaction is shown below.

Figure 4

Conclusion

The product formed by the reaction of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ is shown in Figure 4. The reaction occurs slower because benzene ring contains deactivating group.

Interpretation Introduction

(e)

Interpretation: The products formed when given compound is treated with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ is to be drawn. The reaction occurs faster or slower than a similar reaction with benzene is to be stated.

Concept introduction: Benzene undergoes electrophile substitution. The kinetics of the electrophile substitution reaction depends upon the nature of substituent present on the benzene ring. Electron releasing groups activates the ring towards the electrophilic substitution reaction while electron withdrawing groups deactivates the ring towards the electrophilic substitution reaction.

Answer to Problem 18.16P

The products formed by the reaction of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ are,

The reaction occurs higher because benzene ring contains activating group.

Explanation of Solution

Electron releasing group directs the electrophile to ortho and para positions.

The substituent present in the given compound is electron withdrawing group. Thus it directs the electrophile to ortho and para positions and activates the ring towards the electrophilic substitution reaction. Hence, the given compound reacts faster than benzene. The reaction is shown below.

Figure 5

Conclusion

The product formed by the reaction of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ is shown in Figure 5. The reaction occurs faster because benzene ring contains activating group.