Chapter 18, Problem 18.63P

Synthesize each compound from benzene and any other organic or inorganic reagents.

a. c. e. g.

b. d. f. h.

Interpretation Introduction

(a)

Interpretation: The synthesis of given compound from benzene and any other organic or inorganic reagent is to be stated.

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 18.63P

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown below:

Explanation of Solution

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 1.

Figure 1

The synthesis of given compound takes place by chlorination of benzene, Friedel-Craft acylation and clemmensen reduction at last step.

Conclusion

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: The synthesis of given compound from benzene and any other organic or inorganic reagent is to be stated.

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 18.63P

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown below:

Explanation of Solution

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 2.

Figure 2

The synthesis of given compound take place in four steps: Friedel-Craft alkylation, sulfonation, chlorination and at last oxidation.

Conclusion

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation: The synthesis of given compound from benzene and any other organic or inorganic reagent is to be stated.

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 18.63P

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown below:

Explanation of Solution

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 3.

Figure 3

The first, second, third and fourth step involved in the synthesis of given compound is chlorination, Friedel-Craft acylation, Wittig reaction and nitration, respectively.

Conclusion

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation: The synthesis of given compound from benzene and any other organic or inorganic reagent is to be stated.

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 18.63P

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown below:

Explanation of Solution

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 4.

Figure 4

The first step of the synthesis is Friedel-Craft alkylation reaction. The product of this reaction undergoes nitration reaction. In next step, the ${\text{CH}}_{\text{3}}$ group on reaction with ${\text{KMnO}}_{\text{4}}$ changes to $\text{COOH}$ group and ${\text{NO}}_{\text{2}}$ group on reaction with $\text{Sn,}\text{HCl}$ changes to ${\text{NH}}_{\text{2}}$.

Conclusion

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation: The synthesis of given compound from benzene and any other organic or inorganic reagent is to be stated.

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 18.63P

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown below:

Explanation of Solution

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 5.

Figure 5

Benzene undergoes nitration on reaction with $\text{conc}\text{.}{\text{HNO}}_{\text{3}}\text{,}{\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ and leads to the formation of nitrobenzene. The nitro group changes to ${\text{NH}}_{\text{2}}$ on reaction with $\text{Sn,}\text{HCl}$. The product obtained by the bromination of aniline on Friedel-Craft acylation, followed by clemmensen reduction, leads to the formation of desired product.

Conclusion

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 5.

Interpretation Introduction

(f)

Interpretation: The synthesis of given compound from benzene and any other organic or inorganic reagent is to be stated.

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 18.63P

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown below:

Explanation of Solution

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 6.

Figure 6

Benzene on Friedel-Craft alkylation with ethylchloride gives ethylbenzene. This product undergoes bromination in presence of light. The next step involves the abstraction of bromine on reaction with tertiary butoxide. This leads to the formation of $\text{C}=\text{C}$ bond. The Friedel-Craft acylation followed by clemmensen reduction and chlorination of this product leads to the formation of given compound.

Conclusion

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 6.

Interpretation Introduction

(g)

Interpretation: The synthesis of given compound from benzene and any other organic or inorganic reagent is to be stated.

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 18.63P

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown below:

Explanation of Solution

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 7.

Figure 7

The first two steps involved in the synthesis of given compound are Friedel-Craft alkylation followed by chlorination in the presence of light. The chlorine group is replaced by hydroxyl group on reaction with $\text{KOH}$. This product undergoes reaction with ${\text{CH}}_{\text{3}}{\left({\text{CH}}_{\text{2}}\right)}_{\text{3}}\text{I}$ in presence of $\text{NaH}$, followed by Friedel-Craft acylation and bromination.

Conclusion

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 7.

Interpretation Introduction

(h)

Interpretation: The synthesis of given compound from benzene and any other organic or inorganic reagent is to be stated.

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 18.63P

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown below:

Explanation of Solution

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 8.

Figure 8

Benzene on Friedel-Craft alkylation with ethylchloride gives ethylbenzene. This product undergoes bromination in presence of light. The next step involves the abstraction of bromine on reaction with tertiary butoxide. This leads to the formation of $\text{C}=\text{C}$ bond. The product further reacts with ${\text{OsO}}_{\text{4}}$ and gives rise to diol. The Friedel-Craft acylation and nitration of this product leads to the formation of given compound.

Conclusion

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 8.