Chapter 16, Problem 37P

Interpretation Introduction

(a)

Interpretation: The products formed by the treatment of A and B with reagent ${\text{Br}}_{\text{2}}\text{,}{\text{FeBr}}_{\text{3}}$ 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 37P

The products formed by the treatment of A and B with reagent ${\text{Br}}_{\text{2}}\text{,}{\text{FeBr}}_{\text{3}}$ are shown below.

Explanation of Solution

In the given ball and stick model of A and B, black balls represent carbon atoms, white balls represent hydrogen atoms, red balls represent oxygen atoms, blue ball represents nitrogen atom and brown ball represents bromine atom. Therefore, the structure of A and B is,

Figure 1

Reagent ${\text{Br}}_{\text{2}}\text{,}{\text{FeBr}}_{\text{3}}$ is used for the bromination of aromatic compounds. The $-\text{OCH}{\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}$ and $-\text{NHC}\left(\text{O}\right){\text{CH}}_{\text{3}}$ groups are electron releasing groups whereas $-\text{CHO}$ and $-\text{Br}$ groups are electron withdrawing groups. The electron withdrawing group directs the incoming electrophile to meta position whereas electron releasing group directs incoming electrophile to ortho and para position.

Hence, the products obtained from the treatment of A and B with reagent ${\text{Br}}_{\text{2}}\text{,}{\text{FeBr}}_{\text{3}}$ are,

Figure 2

Conclusion

The products formed by the treatment of A and B with reagent ${\text{Br}}_{\text{2}}\text{,}{\text{FeBr}}_{\text{3}}$ are shown in Figure 2.

Interpretation Introduction

(b)

Interpretation: The products formed by the treatment of A and B with reagent ${\text{HNO}}_3\text{,}{\text{H}}_2{\text{SO}}_4$ 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 37P

The products formed by the treatment of A and B with reagent ${\text{HNO}}_3\text{,}{\text{H}}_2{\text{SO}}_4$ are shown below.

Explanation of Solution

The structure of A and B is shown in Figure 1.

Reagent ${\text{HNO}}_3\text{,}{\text{H}}_2{\text{SO}}_4$ is used for the nitration of aromatic compounds. The $-\text{OCH}{\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}$ and $-\text{NHC}\left(\text{O}\right){\text{CH}}_{\text{3}}$ groups are electron releasing groups whereas $-\text{CHO}$ and $-\text{Br}$ groups are electron withdrawing groups. The electron withdrawing group directs the incoming electrophile to meta position whereas electron releasing group directs incoming electrophile to ortho and para position.

Hence, the products obtained from the treatment of A and B with reagent ${\text{HNO}}_3\text{,}{\text{H}}_2{\text{SO}}_4$ are,

Figure 3

Conclusion

The products formed by the treatment of A and B with reagent ${\text{HNO}}_3\text{,}{\text{H}}_2{\text{SO}}_4$ are shown in Figure 3.

Interpretation Introduction

(c)

Interpretation: The products formed by the treatment of A and B with reagent ${\text{CH}}_3{\text{CH}}_2\text{COCl,}{\text{AlCl}}_{\text{3}}$ 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 37P

The products formed by the treatment of A and B with reagent ${\text{CH}}_3{\text{CH}}_2\text{COCl,}{\text{AlCl}}_{\text{3}}$ are shown below.

Explanation of Solution

The structure of A and B is shown in Figure 1.

Reagent ${\text{CH}}_3{\text{CH}}_2\text{COCl,}{\text{AlCl}}_{\text{3}}$ is used for the Friedel-Craft acylation of aromatic compounds. The $-\text{OCH}{\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}$ and $-\text{NHC}\left(\text{O}\right){\text{CH}}_{\text{3}}$ groups are electron releasing groups whereas $-\text{CHO}$ and $-\text{Br}$ groups are electron withdrawing groups. The electron withdrawing group directs the incoming electrophile to meta position whereas electron releasing group directs incoming electrophile to ortho and para position.

Hence, the products obtained from the treatment of A and B with reagent ${\text{CH}}_3{\text{CH}}_2\text{COCl,}{\text{AlCl}}_{\text{3}}$ are,

Figure 4

Conclusion

The products formed by the treatment of A and B with reagent ${\text{CH}}_3{\text{CH}}_2\text{COCl,}{\text{AlCl}}_{\text{3}}$ are shown in Figure 4.