Chapter 18, Problem 18.38P

Draw the products of each reaction.

a. e. i.

b. f. j.

c. g.

d. h.

Interpretation Introduction

(a)

Interpretation: The products of given reaction 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 18.38P

The products of given reaction are shown below:

Explanation of Solution

An aromatic compound undergoes sulphonation on reaction with ${\text{SO}}_3$ in the presence of ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$. This reagent generates sulphonium ion ${}^{+}{\text{SO}}_{\text{3}}\text{H}$ which acts as electrophile. The $\text{CN}$ group is electron withdrawing group and the position of incoming electrophile is meta-position. Therefore, the products of given reaction are,

Figure 1

Conclusion

The products of given reaction are shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: The products of given reaction 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 18.38P

The products of given reaction are shown below:

Explanation of Solution

An aromatic compound undergoes nitration on reaction with ${\text{HNO}}_3$ in the presence of ${\text{H}}_2{\text{SO}}_4$. The $\text{OH}$ group and ${\text{NO}}_{\text{2}}$ group are an electron donating and electron withdrawing group, respectively. The position of incoming nitro group is determined by $\text{OH}$ group as its $+\text{R}$ effect is more than the $-\text{R}$ effect of ${\text{NO}}_{\text{2}}$ group. Therefore, the products of given reaction are,

Figure 2

Conclusion

The products of given reaction are shown in Figure 2.

Interpretation Introduction

(c)

Interpretation: The products of given reaction 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 18.38P

The products of given reaction are shown below:

Explanation of Solution

An aromatic compound undergoes sulphonation on reaction with ${\text{SO}}_3$ in the presence of ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$. This reagent generates sulphonium ion ${}^{+}{\text{SO}}_{\text{3}}\text{H}$ which acts as electrophile. The $\text{OH}$ group is electron donating group and strongly activating while methyl group is weakly activating. The position of incoming electrophile is ortho/paraposition. Therefore, the products of given reaction are,

Figure 3

Conclusion

The products of given reaction are shown in Figure 3.

Interpretation Introduction

(d)

Interpretation: The products of given reaction 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 18.38P

The products of given reaction are shown below:

Explanation of Solution

An aromatic compound undergoes Friedel-Craft alkylation on reaction with $\text{RCl}$ in the presence of ${\text{AlCl}}_{\text{3}}$. The $\text{Cl}$ group and $\text{OC}\left(\text{O}\right)\text{R}$ group is ortho-para directive. However, the position of incoming alkyl group is determined by $\text{OC}\left(\text{O}\right)\text{R}$ group as its $+\text{R}$ effect is more than the $+\text{R}$ effect of $\text{Cl}$ group. Therefore, the products of given reaction are,

Figure 4

Conclusion

The products of given reaction are shown in Figure 4.

Interpretation Introduction

(e)

Interpretation: The products of given reaction 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 18.38P

The products of given reaction are shown below:

Explanation of Solution

An aromatic compound undergoes bromination on reaction with ${\text{Br}}_2$ in the presence of ${\text{FeBr}}_{\text{3}}$. The $\text{CHO}$ group and ${\text{CH}}_3$ group is meta and ortho-para directive, respectively. Therefore, the products of given reaction are,

Figure 5

Conclusion

The products of given reaction are shown in Figure 5.

Interpretation Introduction

(f)

Interpretation: The products of given reaction 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 18.38P

The products of given reaction are shown below:

Explanation of Solution

An aromatic compound undergoes Friedel-Craft acylation on reaction with $\text{RCOCl}$ in the presence of ${\text{AlCl}}_{\text{3}}$. The ${\text{NHCOCH}}_{\text{3}}$ group is ortho-para directive and ${\text{OCOCH}}_{\text{3}}$ is meta directing. However, the position of incoming acyl group is determined by ${\text{NHCOCH}}_{\text{3}}$ group as its $+\text{R}$ effect and $-\text{R}$ effect of ${\text{OCOCH}}_{\text{3}}$ group. Therefore, the product of given reaction is,

Figure 6

Conclusion

The products of given reaction are shown in Figure 6.

Interpretation Introduction

(g)

Interpretation: The products of given reaction 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 18.38P

The products of given reaction are shown below:

Explanation of Solution

An aromatic compound undergoes nitration on reaction with ${\text{HNO}}_3$ in the presence of ${\text{H}}_2{\text{SO}}_4$. The ${\text{NO}}_{\text{2}}$ group is an electron withdrawing group. The position of incoming nitro group is determined by the $-\text{R}$ effect of ${\text{NO}}_{\text{2}}$ group. Therefore, the product of given reaction is,

Figure 7

Conclusion

The products of given reaction are shown in Figure 7.

Interpretation Introduction

(h)

Interpretation: The products of given reaction 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 18.38P

The products of given reaction are shown below:

Explanation of Solution

An aromatic compound undergoes chlorination on reaction with ${\text{Cl}}_2$ in the presence of ${\text{FeCl}}_3$. The $-{\text{OCH}}_3$ group and $-\text{C}\left(\text{O}\right){\text{OCH}}_3$ group is ortho-para and meta directive, respectively. Therefore, the products of given reaction are,

Figure 8

Conclusion

The products of given reaction are shown in Figure 8.

Interpretation Introduction

(i)

Interpretation: The products of given reaction 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 18.38P

The products of given reaction are shown below:

Explanation of Solution

An aromatic compound undergoes sulfonation on reaction with ${\text{SO}}_3$ in the presence of ${\text{H}}_2{\text{SO}}_4$. The $-{\text{OCH}}_3$ group and $-\text{Br}$ group are ortho-para directive. The $+\text{R}$ effect of $-{\text{OCH}}_3$ group is more than the $+\text{R}$ effect of $-\text{Br}$ group. Therefore, the products of given reaction are,

Figure 9

Conclusion

The products of given reaction are shown in Figure 9.

Interpretation Introduction

(j)

Interpretation: The products of given reaction 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 18.38P

The products of given reaction are shown below:

Explanation of Solution

In the given reaction, ${}^{-}{\text{SCH}}_{\text{2}}{\text{CH}}_{\text{3}}$ acts like a nucleophile. It attacks on the electron deficient carbon atom on benzene ring and undergo nucleophilic aromatic substitution reaction by addition-elimination. Therefore, the products of given reaction are,

Figure 10

Conclusion

The products of given reaction are shown in Figure 10.