Chapter 18, Problem 18.22P

Draw the products formed when each compound is treated with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$.

a. b. c. d.

Interpretation Introduction

(a)

Interpretation: The products formed by the treatment of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_4$ 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 18.22P

The products formed by the treatment of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_4$ are drawn below.

Explanation of Solution

The aromatic compound on reaction with ${\text{HNO}}_{\text{3}}$ in presence of ${\text{H}}_{\text{2}}{\text{SO}}_4$ undergoes nitration reaction. The electron withdrawing groups present on a benzene ring direct ${\text{NO}}_{\text{2}}$ group to meta position whereas electron donating groups direct it to ortho and para position.

The structure of given compound shows that benzene ring is substituted by $-{\text{OCH}}_3$ and ${\text{CH}}_{\text{3}}\text{OC}\left(\text{O}\right)-$ groups. The $-{\text{OCH}}_3$ and ${\text{CH}}_{\text{3}}\text{OC}\left(\text{O}\right)-$ groups are electron releasing and electron withdrawing, respectively. The nitration of given compound takes place ortho to $-{\text{OCH}}_3$ group and meta to ${\text{CH}}_{\text{3}}\text{OC}\left(\text{O}\right)-$ group. The product formed by the treatment of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_4$ is shown in Figure 1.

Figure 1

Conclusion

The products formed by the treatment of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_4$ are shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: The products formed by the treatment of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_4$ 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 18.22P

The products formed by the treatment of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_4$ are drawn below.

Explanation of Solution

The aromatic compound on reaction with ${\text{HNO}}_{\text{3}}$ in presence of ${\text{H}}_{\text{2}}{\text{SO}}_4$ undergoes nitration reaction. The electron withdrawing groups present on a benzene ring direct ${\text{NO}}_{\text{2}}$ group to meta position whereas electron donating groups direct it to ortho and para position.

The structure of given compound shows that benzene ring is substituted by $-{\text{OCH}}_3$ and $\text{Br}-$ groups. The $-{\text{OCH}}_3$ and $\text{Br}-$ groups are electron releasing and electron withdrawing, respectively. However, $\text{Br}$ directs incoming nitro group to ortho and para position. The productd formed by the treatment of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_4$ are shown in Figure 2.

Figure 2

Conclusion

The products formed by the treatment of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_4$ are shown in Figure 2.

Interpretation Introduction

(c)

Interpretation: The products formed by the treatment of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_4$ 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 18.22P

The products formed by the treatment of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_4$ are drawn below.

Explanation of Solution

The aromatic compound on reaction with ${\text{HNO}}_{\text{3}}$ in presence of ${\text{H}}_{\text{2}}{\text{SO}}_4$ undergoes nitration reaction. The electron withdrawing groups present on a benzene ring direct ${\text{NO}}_{\text{2}}$ group to meta position whereas electron donating groups direct it to ortho and para position.

The structure of given compound shows that benzene ring is substituted by $-{\text{CH}}_3$ and $-{\text{NO}}_{\text{2}}$ groups. The $-{\text{CH}}_3$ and $-{\text{NO}}_{\text{2}}$ groups are electron releasing and electron withdrawing, respectively. The nitration of given compound takes place ortho and para to $-{\text{CH}}_3$ group and meta to $-{\text{NO}}_{\text{2}}$ group. The product formed by the treatment of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_4$ is shown in Figure 3.

Figure 3

Conclusion

The products formed by the treatment of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_4$ are shown in Figure 3.

Interpretation Introduction

(d)

Interpretation: The products formed by the treatment of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_4$ 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 18.22P

The products formed by the treatment of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_4$ are drawn below.

Explanation of Solution

The aromatic compound on reaction with ${\text{HNO}}_{\text{3}}$ in presence of ${\text{H}}_{\text{2}}{\text{SO}}_4$ undergoes nitration reaction. The electron withdrawing groups present on a benzene ring direct ${\text{NO}}_{\text{2}}$ group to meta position whereas electron donating groups direct it to ortho and para position.

The structure of given compound shows that benzene ring is substituted by $-\text{Cl}$ and $-\text{Br}$ groups. The $-\text{Cl}$ and $-\text{Br}$ groups are electron withdrawing groups. However, they directs the incoming nitro group to ortho and meta position. The products formed by the treatment of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_4$ are shown in Figure 4.

Figure 4

Conclusion

The products formed by the treatment of given compound with ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_4$ are shown in Figure 4.