Chapter 18, Problem 18.66P

Synthesize each compound from toluene $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{CH}}_{\text{3}}\right)$ and any other organic or inorganic reagents.

a. ${\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{CH}}_{\text{2}}{\text{OC(CH}}_{\text{3}}{\text{)}}_{\text{3}}$

b. ${\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{CHO}$ d. f.

c. e. g.

Interpretation Introduction

(a)

Interpretation: The synthesis of given compound from toluene 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 18.66P

The synthesis of given compound from toluene by the use of organic and inorganic reagent is shown below:

Explanation of Solution

The synthesis of given compound from toluene by the use of organic and inorganic reagent is shown below.

Figure 1

The first step of the synthesis is monobromination of methyl group of toluene in presence of light. The product obtained is treated with tertiary butanol to form desired ether.

Conclusion

The synthesis of given compound from toluene by the use of organic and inorganic reagent is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: The synthesis of given compound from toluene 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 18.66P

The synthesis of given compound from toluene by the use of organic and inorganic reagent is shown below:

Explanation of Solution

The synthesis of given compound from toluene by the use of organic and inorganic reagent is shown in Figure 1.

Figure 2

Toluene undergoes Etard’s reaction using inorganic reagent ${\text{CrO}}_{\text{2}}{\text{Cl}}_{\text{2}}$, to form benzaldehyde.

Conclusion

The synthesis of given compound from toluene by the use of organic and inorganic reagent is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation: The synthesis of given compound from toluene 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 18.66P

The synthesis of given compound from toluene by the use of organic and inorganic reagent is shown below:

Explanation of Solution

The synthesis of given compound from toluene by the use of organic and inorganic reagent is shown below.

Figure 3

Toluene undergoes chlorination on ortho and para position, but for the synthesis ortho product is required. This ortho product is oxidized using potassium permanganate to form the desired product.

Conclusion

The synthesis of given compound from toluene by the use of organic and inorganic reagent is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation: The synthesis of given compound from toluene 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 18.66P

The synthesis of given compound from toluene by the use of organic and inorganic reagent is shown below:

Explanation of Solution

The synthesis of given compound from toluene by the use of organic and inorganic reagent is shown below.

Figure 4

Toluene undergoes nitration on ortho and para position, but for the synthesis para product is required. This product again undergoes nitration on the meta position to nitro product. This product is oxidized using potassium permanganate to form the desired product.

Conclusion

The synthesis of given compound from toluene by the use of organic and inorganic reagent is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation: The synthesis of given compound from toluene 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 18.66P

The synthesis of given compound from toluene by the use of organic and inorganic reagent is shown below:

Explanation of Solution

The synthesis of given compound from toluene by the use of organic and inorganic reagent is shown below.

Figure 5

The first step of the synthesis is bromination of toluene which is followed by Friedel-Craft acylation. The product obtained by the Friedel-Craft acylation undergoes bromination at allylic carbon atom and on further reaction with strong base bromine group is replaced by hydroxyl group. This leads to the formation of desired product.

Conclusion

The synthesis of given compound from toluene by the use of organic and 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 18.66P

The synthesis of given compound from toluene by the use of organic and inorganic reagent is shown below:

Explanation of Solution

The synthesis of given compound from toluene by the use of organic and inorganic reagent is shown below.

Figure 6

The first step of the synthesis is Friedel-Craft acylation of toluene which is followed by nitration reaction. The product obtained by nitration undergoes reduction in presence of $\text{Sn,}\text{HCl}$. The nitro group changes to ${\text{NH}}_{\text{2}}$ on reduction. At last, Clemmenson reduction takes place which leads to the formation of desired product.

Conclusion

The synthesis of given compound from toluene by the use of organic and 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 18.66P

The synthesis of given compound from toluene by the use of organic and inorganic reagent is shown below:

Explanation of Solution

The synthesis of given compound from toluene by the use of organic and inorganic reagent is shown below.

Figure 7

The first step of the synthesis is Friedel-Craft acylation of toluene which is followed by chlorination. The product obtained by chlorination undergoes bromination at allylic carbon atom and on further reaction with strong base bromine group is replaced by hydroxyl group. The $\text{OH}$ group is converted to $\text{CHO}$ on reaction with Pyridinium chlorochromate (PCC). This leads to the formation of desired product.

Conclusion

The synthesis of given compound from toluene by the use of organic and inorganic reagent is shown in Figure 7.