Chapter 18, Problem 18.64P

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

a. $o-\text{butylchlorobenzene}$

b. $m-\text{bromonitrobenzene}$

c. d. e. f. g.

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 18.64P

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 first step in the synthesis is the chlorination of benzene. The next step is the Friedel-Craft acylation in which chlorobenzene reacts with butnoyl chloride. The last step is the clemmensen reduction to form the desired product.

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 18.64P

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 first step in the synthesis is the formation of nitrobenzene. The next step is the reaction of nitrobenzene with bromine in the presence of aluminum chloride to give the final product.

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 18.64P

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 step in the synthesis is the conversion of benzene into toluene. The next step is the reaction of toluene with concentrated sulfuric acid which results the addition of sulphonyl group at ortho position. The last step is the oxidation of methyl group into acid in the presence of potassium permanganate to give the final product.

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 18.64P

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 in the synthesis is the conversion of benzene into toluene. The next step is the oxidation of methyl group into acid in the presence of potassium permanganate to give benzoic acid followed by the reaction with methanol to form methyl benzoate. The reaction of nitric acid in the presence of sulphuric acid results in the formation of final product.

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 18.64P

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

The first step in the synthesis is the conversion of benzene into toluene. The next step is the reaction of toluene with bromine in the presence of aluminum chloride. The last step is the oxidation of methyl group into acid in the presence of potassium permanganate to give the final 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 18.64P

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

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 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 18.64P

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 7

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 7.