Chapter 17, Problem 17.50SP

(a)

Interpretation Introduction

To determine: The major product that is formed by reaction of benzene with $tert-\text{butyl}\text{bromide}$ in the presence of ${\text{AlCl}}_3$.

Interpretation: The major product that is formed by reaction of benzene with $tert-\text{butyl}\text{bromide}$ in the presence of ${\text{AlCl}}_3$ is to be predicted.

Concept introduction: Friedel-Crafts alkylation permits the synthesis of alkylated products by the reaction of arenes with alkyl chlorides in the presence of aluminium chloride (Lewis acid). This alkylation reaction comes under the category of electrophilic aromatic substitution.

Answer to Problem 17.50SP

The major product that is formed by reaction of benzene with $tert-\text{butyl}\text{bromide}$ in the presence of ${\text{AlCl}}_3$ is shown as follows.

Explanation of Solution

The major product that is formed by reaction of benzene with $tert-\text{butyl}\text{bromide}$ in the presence of ${\text{AlCl}}_3$ is shown in Figure $1$.

Figure $1$

In the above reaction, benzene reacts with $tert-\text{butyl}\text{bromide}$ in the presence of ${\text{AlCl}}_3$ (Lewis acid) that forms $tert-\text{butyl}\text{benzene}$ as a desired product.

(b)

Interpretation Introduction

To determine: The major product that is formed by reaction of benzene with $1-\text{chlorobutane}$ in the presence of ${\text{AlCl}}_3$.

Interpretation: The major product that is formed by reaction of benzene with $1-\text{chlorobutane}$ in the presence of ${\text{AlCl}}_3$ is to be predicted.

Concept introduction: Friedel-Crafts alkylation permits the synthesis of alkylated products by the reaction of arenes with alkyl chlorides in the presence of aluminium chloride (Lewis acid). This alkylation reaction comes under the category of electrophilic aromatic substitution.

Answer to Problem 17.50SP

The major product that is formed by reaction of benzene with $1-\text{chlorobutane}$ in the presence of ${\text{AlCl}}_3$ is shown as follows.

Explanation of Solution

The major product that is formed by reaction of benzene with $1-\text{chlorobutane}$ in the presence of ${\text{AlCl}}_3$ is shown in Figure $2$.

Figure $2$

In the above reaction, benzene reacts with $1-\text{chlorobutane}$ in the presence of ${\text{AlCl}}_3$ (Lewis acid) that forms $2-\text{phenylbutane}$ as a desired product.

(c)

Interpretation Introduction

To determine: The major product that is formed by reaction of benzene with isobutyl alcohol in the presence of ${\text{BF}}_3$.

Interpretation: The major product that is formed by reaction of benzene with isobutyl alcohol in the presence of ${\text{BF}}_3$ is to be predicted.

Concept introduction: Friedel-Crafts alkylation permits the synthesis of alkylated products by the reaction of arenes with alcohol in the presence of ${\text{BF}}_{\text{3}}$ (Lewis acid). In this alkylation carbocation is generated that rearranges itself to get stability. This alkylation reaction comes under the category of electrophilic aromatic substitution.

Answer to Problem 17.50SP

The major product that is formed by reaction of benzene with isobutyl alcohol in the presence of ${\text{BF}}_3$ is shown as follows.

Explanation of Solution

The major product that is formed by reaction of benzene with isobutyl alcohol in the presence of ${\text{BF}}_3$ is shown in Figure $3$.

Figure $3$

In the above reaction, the primary carbocation that is generated by the protonation of isobutyl alcohol by ${\text{BF}}_3$ (Lewis acid) rearranges itself by hydride shift to get the stability as tertiary carbocation which behaves as an electrophile.

In the second step, this electrophilic carbocation reacts with benzene in the presence of ${\text{AlCl}}_3$ to form the desired products that is $tert-\text{butylbenzene}$ as shown in Figure $3$.

(d)

Interpretation Introduction

To determine: The major product that is formed by reaction of benzene with bromine in the presence of a nail.

Interpretation: The major product that is formed by reaction of benzene with bromine in the presence of a nail is to be predicted.

Concept introduction: The reaction that includes the addition of one or more bromine atoms in a compound is known as bromination reaction. Bromination reaction is a type of halogenation reaction.

Answer to Problem 17.50SP

The major product that is formed by reaction of benzene with bromine in the presence of a nail is shown as follows.

Explanation of Solution

The major product that is formed by reaction of benzene with bromine in the presence of a nail is shown in Figure $4$.

Figure $4$

In the above reaction, bromination of benzene ring occurs to form bromobenzene as the desired product.

(e)

Interpretation Introduction

To determine: The major product that is formed by reaction of benzene with isobutylene in the presence of $\text{HF}$.

Interpretation: The major product that is formed by reaction of benzene with isobutylene in the presence of $\text{HF}$ is to be predicted.

Concept introduction: Friedel-Crafts alkylation permits the synthesis of alkylated products by the reaction of arenes with alkene in the presence of $\text{HF}$ (Lewis acid). In this alkylation carbocation is generated that rearranges itself to get stability. This alkylation reaction comes under the category of electrophilic aromatic substitution.

Answer to Problem 17.50SP

The major product that is formed by reaction of benzene with isobutylene in the presence of $\text{HF}$ is shown as follows.

Explanation of Solution

The major product that is formed by reaction of benzene with isobutylene in the presence of $\text{HF}$ is shown in Figure $5$.

Figure $5$

In the above reaction, benzene reacts with isobutylene in the presence of $\text{HF}$ to form $tert-\text{butylbenzene}$ as the desired product.

(f)

Interpretation Introduction

To determine: The major product that is formed by reaction of benzene with fuming sulphuric acid.

Interpretation: The major product that is formed by reaction of benzene with fuming sulphuric acid is to be predicted.

Concept introduction: The process of attaching ${\text{SO}}_{\text{3}}\text{H}$ group with an aromatic or alkyl compound in the presence of fuming sulphuric acid is known as sulfonation of that compound.

Answer to Problem 17.50SP

The major product that is formed by reaction of benzene with fuming sulphuric acid is shown as follows.

Explanation of Solution

The major product that is formed by reaction of benzene with fuming sulphuric acid is shown in Figure $6$.

Figure $6$

In the above reaction, benzene reacts with fuming sulphuric acid to form as the desired sulfonated product.

(g)

Interpretation Introduction

To determine: The major product that is formed by reaction of benzene with $1-\text{chloro}-2,2-\text{dimethylpropane}$ in the presence of ${\text{AlCl}}_3$.

Interpretation: The major product that is formed by reaction of benzene with $1-\text{chloro}-2,2-\text{dimethylpropane}$ in the presence of ${\text{AlCl}}_3$ is to be predicted.

Concept introduction: Friedel-Crafts alkylation permits the synthesis of alkylated products by the reaction of arenes with alkyl chlorides in the presence of aluminium chloride (Lewis acid). This alkylation reaction comes under the category of electrophilic aromatic substitution.

Answer to Problem 17.50SP

The major product that is formed by reaction of benzene with $1-\text{chloro}-2,2-\text{dimethylpropane}$ in the presence of ${\text{AlCl}}_3$ is shown as follows.

Explanation of Solution

The major product that is formed by reaction of benzene with $1-\text{chloro}-2,2-\text{dimethylpropane}$ in the presence of ${\text{AlCl}}_3$ is shown in Figure $7$.

Figure $7$

In the above reaction, benzene reacts with $1-\text{chloro}-2,2-\text{dimethylpropane}$ in the presence of ${\text{AlCl}}_3$ (Lewis acid) that forms the desired product.

(h)

Interpretation Introduction

To determine: The major product that is formed by reaction of benzene with benzoyl chloride in the presence of ${\text{AlCl}}_3$.

Interpretation: The major product that is formed by reaction of benzene with benzoyl chloride in the presence of ${\text{AlCl}}_3$ is to be predicted.

Concept introduction: Friedel-Crafts alkylation permits the synthesis of alkylated products by the reaction of arenes with alkyl chlorides in the presence of aluminium chloride (Lewis acid). This alkylation reaction comes under the category of electrophilic aromatic substitution.

Answer to Problem 17.50SP

The major product that is formed by reaction of benzene with benzoyl chloride in the presence of ${\text{AlCl}}_3$ is shown as follows.

Explanation of Solution

The major product that is formed by reaction of benzene with benzoyl chloride in the presence of ${\text{AlCl}}_3$ is shown in Figure $8$.

Figure $8$

In the above reaction, benzene reacts with benzoyl chloride in the presence of ${\text{AlCl}}_3$ (Lewis acid) that forms diphenyl ketone as the desired product.

(i)

Interpretation Introduction

To determine: The major product that is formed by reaction of benzene with iodine molecule in the presence of ${\text{HNO}}_{\text{3}}$.

Interpretation: The major product that is formed by reaction of benzene with iodine molecule in the presence of ${\text{HNO}}_{\text{3}}$ is to be predicted.

Concept introduction: The reaction that includes the addition of one or more than one halogen atoms in a compound is known as halogenation reaction.

Answer to Problem 17.50SP

The major product that is formed by reaction of benzene with iodine molecule in the presence of ${\text{HNO}}_{\text{3}}$ is shown as follows.

Explanation of Solution

The major product that is formed by reaction of benzene with iodine molecule in the presence of ${\text{HNO}}_{\text{3}}$ is shown in Figure $9$.

Figure $9$

In the above halogenations reaction, benzene reacts with iodine molecule in the presence of ${\text{HNO}}_{\text{3}}$ that forms iodobenzene as the desired product.

(j)

Interpretation Introduction

To determine: The major product that is formed by reaction of benzene with nitric acid and sulphuric acid.

Interpretation: The major product that is formed by reaction of benzene with nitric acid and sulphuric acid is to be predicted.

Concept introduction: The reaction that involves the addition of a nitro group on an alkyl or an aromatic compound in the presence of concentrated nitric acid and sulphuric acid is known as nitration reaction.

Answer to Problem 17.50SP

The major product that is formed by reaction of benzene with nitric acid and sulphuric acid is shown as follows.

Explanation of Solution

The major product that is formed by reaction of benzene benzene with nitric acid and sulphuric acid is shown in Figure $10$.

Figure $10$

In the above nitration reaction, benzene reacts with concentrated nitric acid and sulphuric acid that forms nitrobenzene as the desired product.

(k)

Interpretation Introduction

To determine: The major product that is formed by reaction of benzene with carbon monoxide in the presence of $\text{HCl}$ and ${\text{AlCl}}_{\text{3}}/\text{CuCl}$.

Interpretation: The major product that is formed by reaction of benzene with carbon monoxide in the presence of $\text{HCl}$ and ${\text{AlCl}}_{\text{3}}/\text{CuCl}$ is to be predicted.

Concept introduction: The synthesis in which aromatic compounds reacts with carbon monoxide, and $\text{HCl}$ in the presence of ${\text{AlCl}}_3$ (Lewis acid) to form an aromatic aldehyde compound is known as Gatterman-Koch synthesis.

Answer to Problem 17.50SP

The major product that is formed by reaction of benzene with carbon monoxide in the presence of $\text{HCl}$ and ${\text{AlCl}}_{\text{3}}/\text{CuCl}$ is shown as follows.

Explanation of Solution

The major product that is formed by reaction of benzene with carbon monoxide in the presence of $\text{HCl}$ and ${\text{AlCl}}_{\text{3}}/\text{CuCl}$ is shown in Figure $11$.

Figure $11$

In the above reaction, benzene reacts with benzoyl carbon monoxide in the presence of $\text{HCl}$ and ${\text{AlCl}}_{\text{3}}/\text{CuCl}$ that forms benzaldehyde as the desired product.

(l)

Interpretation Introduction

To determine: The major product that is formed by reaction of benzene with ${\text{CH}}_{\text{2}}{\left(\text{COCl}\right)}_{\text{2}}$ in the presence of ${\text{AlCl}}_3$.

Interpretation: The major product that is formed by reaction of benzene with ${\text{CH}}_{\text{2}}{\left(\text{COCl}\right)}_{\text{2}}$ in the presence of ${\text{AlCl}}_3$ is to be predicted.

Concept introduction: Friedel-Crafts acylation permits the synthesis of acylated products by the reaction of arenes with acyl chlorides in the presence of ${\text{AlCl}}_3$ (Lewis acid). This acylation reaction comes under the category of electrophilic aromatic substitution.

Answer to Problem 17.50SP

The major product that is formed by reaction of benzene with ${\text{CH}}_{\text{2}}{\left(\text{COCl}\right)}_{\text{2}}$ in the presence of ${\text{AlCl}}_3$ is shown as follows.

Explanation of Solution

The major product that is formed by reaction benzene with ${\text{CH}}_{\text{2}}{\left(\text{COCl}\right)}_{\text{2}}$ in the presence of ${\text{AlCl}}_3$ is shown in Figure $12$.

Figure $12$

In the above reaction, benzene reacts with ${\text{CH}}_{\text{2}}{\left(\text{COCl}\right)}_{\text{2}}$ in the presence of ${\text{AlCl}}_3$ (Lewis acid) that forms ketonic compound as the desired product.