Chapter 18, Problem 18.37P

Interpretation Introduction

(a)

Interpretation: The products formed by the treatment of given compound with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{COCl,}{\text{AlCl}}_3$ are 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 18.37P

The products formed by the treatment of given compound with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{COCl,}{\text{AlCl}}_3$ are shown below:

Explanation of Solution

An aromatic compound undergoes Friedel-Craft acylation on reaction with $\text{ROCl}$ in the presence of ${\text{AlCl}}_{\text{3}}$. The nature of substituent present on the aromatic compound determines the position of acyl group on it. The electron withdrawing group directs an incoming electrophile to meta position whereas the electron donating group directs it to ortho and para position.

In the given compound, benzene ring is attached to an electron releasing group, thus the acyl group will go to ortho and para position as shown in Figure 1.

Figure 1

Conclusion

The products formed by the treatment of given compound with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{COCl,}{\text{AlCl}}_3$ are shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: The products formed by the treatment of given compound with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{COCl,}{\text{AlCl}}_3$ are 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 18.37P

The products formed by the treatment of given compound with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{COCl,}{\text{AlCl}}_3$ are shown below:

Explanation of Solution

An aromatic compound undergoes Friedel-Craft acylation on reaction with $\text{ROCl}$ in the presence of ${\text{AlCl}}_{\text{3}}$. The nature of substituent present on the aromatic compound determines the position of acyl group on it. The electron withdrawing group directs an incoming electrophile to meta position whereas the electron donating group directs it to ortho and para position.

In the given compound, benzene ring is attached to an electron withdrawing group, thus the acyl group will go to meta position as shown in Figure 2.

Figure 2

Conclusion

The products formed by the treatment of given compound with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{COCl,}{\text{AlCl}}_3$ are shown in Figure 2.

Interpretation Introduction

(c)

Interpretation: The products formed by the treatment of given compound with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{COCl,}{\text{AlCl}}_3$ are 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 18.37P

No product will form by the treatment of given compound with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{COCl,}{\text{AlCl}}_3$.

Explanation of Solution

An aromatic compound undergoes Friedel-Craft acylation on reaction with $\text{ROCl}$ in the presence of ${\text{AlCl}}_{\text{3}}$. The nature of substituent present on the aromatic compound determines the position of acyl group on it. The electron withdrawing group directs an incoming electrophile to meta position whereas the electron donating group directs it to ortho and para position.

In the given compound, benzene ring is attached to a strong electron releasing group. However, the Friedel-Craft acylation reaction does not occur in the presence of strong activating groups. Therefore, no product will form by the treatment of given compound with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{COCl,}{\text{AlCl}}_3$.

Conclusion

No product will form by the treatment of given compound with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{COCl,}{\text{AlCl}}_3$.

Interpretation Introduction

(d)

Interpretation: The products formed by the treatment of given compound with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{COCl,}{\text{AlCl}}_3$ are 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 18.37P

The products formed by the treatment of given compound with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{COCl,}{\text{AlCl}}_3$ are shown below:

Explanation of Solution

An aromatic compound undergoes Friedel-Craft acylation on reaction with $\text{ROCl}$ in the presence of ${\text{AlCl}}_{\text{3}}$. The nature of substituent present on the aromatic compound determines the position of acyl group on it. The electron withdrawing group directs an incoming electrophile to meta position whereas the electron donating group directs it to ortho and para position.

In the given compound, benzene ring is attached to an electron withdrawing group bromine which deactivates the benzene ring and it donates electrons through resonance effect. The ortho position is an electron deficient position than para position due to negative inductive effect, thus the acyl group will go to para position as shown in Figure 4.

Figure 4

Conclusion

The products formed by the treatment of given compound with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{COCl,}{\text{AlCl}}_3$ are shown in Figure 4.

Interpretation Introduction

(e)

Interpretation: The products formed by the treatment of given compound with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{COCl,}{\text{AlCl}}_3$ are 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 18.37P

The products formed by the treatment of given compound with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{COCl,}{\text{AlCl}}_3$ are shown below:

Explanation of Solution

An aromatic compound undergoes Friedel-Craft acylation on reaction with $\text{ROCl}$ in the presence of ${\text{AlCl}}_{\text{3}}$. The nature of substituent present on the aromatic compound determines the position of acyl group on it. The electron withdrawing group directs an incoming electrophile to meta position whereas the electron donating group directs it to ortho and para position.

In the given compound, benzene ring is attached to an electron releasing group, thus the acyl group will go to ortho and para position as shown in Figure 2.

Figure 5

Conclusion

The products formed by the treatment of given compound with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{COCl,}{\text{AlCl}}_3$ are shown in Figure 5.