Chapter 25, Problem 25.61P

Interpretation Introduction

(a)

Interpretation:

The product formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with the given reagent is to be drawn.

Concept introduction:

Synthesis is one of the major areas in the field of organic chemistry. It can be a simple one-step reaction or it may involve many steps.

The inorganic reagents do not contain a carbon atom. These reagents generally contain inorganic molecules, but sometimes small organic molecule also acts as an inorganic reagent. The reagents are additional chemical substances that are used to perform various chemical reactions like reduction, oxidation, base, catalysis, and the addition of functional groups.

Answer to Problem 25.61P

The product formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with $\text{HCl}$ is,

Explanation of Solution

The given reagent is $\text{HCl}$. The reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with $\text{HCl}$ is shown below.

Figure 1

The nitrogen atom of p-methylaniline is basic in nature. It abstracts proton from $\text{HCl}$ to form the final product salt.

Conclusion

The product formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with $\text{HCl}$ is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation:

The product formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with the given reagent is to be drawn.

Concept introduction:

Synthesis is one of the major areas in the field of organic chemistry. It can be a simple one-step reaction or it may involve many steps.

The inorganic reagents do not contain a carbon atom. These reagents generally contain inorganic molecules, but sometimes small organic molecule also acts as an inorganic reagent. The reagents are additional chemical substances that are used to perform various chemical reactions like reduction, oxidation, base, catalysis, and the addition of functional groups.

Answer to Problem 25.61P

The products formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\text{CH}}_{\text{3}}\text{COCl}$ are,

Explanation of Solution

The given reagent is ${\text{CH}}_{\text{3}}\text{COCl}$. The reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\text{CH}}_{\text{3}}\text{COCl}$ is shown below.

Figure 2

In the above reaction, acetyl chloride dissociates to form ${\text{CH}}_{\text{3}}{\text{CO}}^{+}$ and ${\text{Cl}}^{-}$. The carbocation, ${\text{CH}}_{\text{3}}{\text{CO}}^{+}$ attacks at the nitrogen atom of p-methylaniline to form the final product.

Conclusion

The products formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\text{CH}}_{\text{3}}\text{COCl}$ are shown in Figure 2.

Interpretation Introduction

(c)

Interpretation:

The product formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with the given reagent is to be drawn.

Concept introduction:

Synthesis is one of the major areas in the field of organic chemistry. It can be a simple one-step reaction or it may involve many steps.

The inorganic reagents do not contain a carbon atom. These reagents generally contain inorganic molecules, but sometimes small organic molecule also acts as an inorganic reagent. The reagents are additional chemical substances that are used to perform various chemical reactions like reduction, oxidation, base, catalysis, and the addition of functional groups.

Answer to Problem 25.61P

The products formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\left({\text{CH}}_{\text{3}}\text{CO}\right)}_{\text{2}}\text{O}$ are,

Explanation of Solution

The given reagent is ${\left({\text{CH}}_{\text{3}}\text{CO}\right)}_{\text{2}}\text{O}$. The reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\left({\text{CH}}_{\text{3}}\text{CO}\right)}_{\text{2}}\text{O}$ is shown below.

Figure 3

In the above reaction, the nucleophilic nitrogen atom attacks at the electrophilic carbonyl carbon atom of acetic anhydride to form the final product amide.

Conclusion

The products formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\left({\text{CH}}_{\text{3}}\text{CO}\right)}_{\text{2}}\text{O}$ are shown in Figure 3.

Interpretation Introduction

(d)

Interpretation:

The product formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with the given reagent is to be drawn.

Concept introduction:

Synthesis is one of the major areas in the field of organic chemistry. It can be a simple one-step reaction or it may involve many steps.

The inorganic reagents do not contain a carbon atom. These reagents generally contain inorganic molecules, but sometimes small organic molecule also acts as an inorganic reagent. The reagents are additional chemical substances that are used to perform various chemical reactions like reduction, oxidation, base, catalysis, and the addition of functional groups.

Answer to Problem 25.61P

The product formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with excess ${\text{CH}}_{\text{3}}\text{I}$ is,

Explanation of Solution

The given reagent is excess ${\text{CH}}_{\text{3}}\text{I}$. The reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with excess ${\text{CH}}_{\text{3}}\text{I}$ is shown below.

Figure 4

In the above reaction, p-methylaniline recats with excess of methyl iodide to form $\text{N, N, N-Trimethyl}$ substituted final product.

Conclusion

The product formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with excess ${\text{CH}}_{\text{3}}\text{I}$ is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation:

The product formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with the given reagent is to be drawn.

Concept introduction:

Synthesis is one of the major areas in the field of organic chemistry. It can be a simple one-step reaction or it may involve many steps.

The inorganic reagents do not contain a carbon atom. These reagents generally contain inorganic molecules, but sometimes small organic molecule also acts as an inorganic reagent. The reagents are additional chemical substances that are used to perform various chemical reactions like reduction, oxidation, base, catalysis, and the addition of functional groups.

Answer to Problem 25.61P

The products formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}=\text{O}$ are,

Explanation of Solution

The given reagent is ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}=\text{O}$. The reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}=\text{O}$ is shown below.

Figure 5

In the above reaction, p-methylaniline reacts with acetone to form the final product.

Conclusion

The products formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}=\text{O}$ are shown in Figure 5.

Interpretation Introduction

(f)

Interpretation:

The product formed by the reaction of p-methylaniline $\left(P{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with the given reagent is to be drawn.

Concept introduction:

Synthesis is one of the major areas in the field of organic chemistry. It can be a simple one-step reaction or it may involve many steps.

The inorganic reagents do not contain a carbon atom. These reagents generally contain inorganic molecules, but sometimes small organic molecule also acts as an inorganic reagent. The reagents are additional chemical substances that are used to perform various chemical reactions like reduction, oxidation, base, catalysis, and the addition of functional groups.

Answer to Problem 25.61P

The product formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\text{CH}}_3{\text{COCl, AlCl}}_3$ is,

Explanation of Solution

The given reagent is ${\text{CH}}_3{\text{COCl, AlCl}}_3$. The reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\text{CH}}_3{\text{COCl, AlCl}}_3$ is shown below.

Figure 6

In the above reaction, acetyl chloride dissociates to form ${\text{CH}}_{\text{3}}{\text{CO}}^{+}$ and ${\text{Cl}}^{-}$. The carbocation, ${\text{CH}}_{\text{3}}{\text{CO}}^{+}$ attacks at the ortho position of p-methylaniline to form the final product.

Conclusion

The product formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\text{CH}}_3{\text{COCl, AlCl}}_3$ is shown in Figure 6.

Interpretation Introduction

(g)

Interpretation:

The product formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with the given reagent is to be drawn.

Concept introduction:

Synthesis is one of the major areas in the field of organic chemistry. It can be a simple one-step reaction or it may involve many steps.

The inorganic reagents do not contain a carbon atom. These reagents generally contain inorganic molecules, but sometimes small organic molecule also acts as an inorganic reagent. The reagents are additional chemical substances that are used to perform various chemical reactions like reduction, oxidation, base, catalysis, and the addition of functional groups.

Answer to Problem 25.61P

The product formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\text{CH}}_{\text{3}}\text{COOH}$ is,

Explanation of Solution

The given reagent is ${\text{CH}}_{\text{3}}\text{COOH}$. The reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\text{CH}}_{\text{3}}\text{COOH}$ is shown below.

Figure 7

The nitrogen atom of p-methylaniline is basic in nature. It abstracts proton from ${\text{CH}}_{\text{3}}\text{COOH}$ to form the final product salt.

Conclusion

The product formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\text{CH}}_{\text{3}}\text{COOH}$ is shown in Figure 7.

Interpretation Introduction

(h)

Interpretation:

The product formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with the given reagent is to be drawn.

Concept introduction:

Synthesis is one of the major areas in the field of organic chemistry. It can be a simple one-step reaction or it may involve many steps.

The inorganic reagents do not contain a carbon atom. These reagents generally contain inorganic molecules, but sometimes small organic molecule also acts as an inorganic reagent. The reagents are additional chemical substances that are used to perform various chemical reactions like reduction, oxidation, base, catalysis, and the addition of functional groups.

Answer to Problem 25.61P

The product formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\text{NaNO}}_{\text{2}}\text{, HCl}$ is,

Explanation of Solution

The given reagent is ${\text{NaNO}}_{\text{2}}\text{, HCl}$. The reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\text{NaNO}}_{\text{2}}\text{, HCl}$ is shown below.

Figure 8

Diazonium salts are prepared by the treatment of aromatic amines with nitrous acid and additional acid. In the above reaction, p-methylaniline reacts with nitrous acid in the presence of hydrochloric acid to form the diazonium salt.

Conclusion

: The product formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\text{NaNO}}_{\text{2}}\text{, HCl}$ is shown in Figure 8.

Interpretation Introduction

(i)

Interpretation:

The product formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with the given reagent is to be drawn.

Concept introduction:

Synthesis is one of the major areas in the field of organic chemistry. It can be a simple one-step reaction or it may involve many steps.

The inorganic reagents do not contain a carbon atom. These reagents generally contain inorganic molecules, but sometimes small organic molecule also acts as an inorganic reagent. The reagents are additional chemical substances that are used to perform various chemical reactions like reduction, oxidation, base, catalysis, and the addition of functional groups.

Answer to Problem 25.61P

The product formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\text{CH}}_{\text{3}}\text{COCl}$ and ${\text{CH}}_3{\text{COCl, AlCl}}_3$ is,

Explanation of Solution

The given reagent is ${\text{CH}}_{\text{3}}\text{COCl}$ and ${\text{CH}}_3{\text{COCl, AlCl}}_3$. The reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\text{CH}}_{\text{3}}\text{COCl}$ and ${\text{CH}}_3{\text{COCl, AlCl}}_3$ is shown below.

Figure 9

In the above reaction, acetyl chloride dissociates to form ${\text{CH}}_{\text{3}}{\text{CO}}^{+}$ and ${\text{Cl}}^{-}$. The carbocation, ${\text{CH}}_{\text{3}}{\text{CO}}^{+}$ attacks at the ortho position of p-methylaniline to form the final product.

Conclusion

The product formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\text{CH}}_{\text{3}}\text{COCl}$ and ${\text{CH}}_3{\text{COCl, AlCl}}_3$ is shown in Figure 9.

Interpretation Introduction

(j)

Interpretation:

The product formed by the reaction of P-methylaniline $\left(P{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with the given reagent is to be drawn.

Concept introduction:

Synthesis is one of the major areas in the field of organic chemistry. It can be a simple one-step reaction or it may involve many steps.

The inorganic reagents do not contain a carbon atom. These reagents generally contain inorganic molecules, but sometimes small organic molecule also acts as an inorganic reagent. The reagents are additional chemical substances that are used to perform various chemical reactions like reduction, oxidation, base, catalysis, and the addition of functional groups.

Answer to Problem 25.61P

The product formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\text{CH}}_3{\text{CHO, NaBH}}_{\text{3}}\text{CN}$ is,

Explanation of Solution

The given reagent is ${\text{CH}}_3{\text{CHO, NaBH}}_{\text{3}}\text{CN}$. The reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\text{CH}}_3{\text{CHO, NaBH}}_{\text{3}}\text{CN}$ is shown below.

Figure 10

When an aldehyde or a ketone is converted to an amine, the process is known as reductive amination. The conversion takes place through the formation of an intermediate known as imine. The excess ammonia is used when a primary amine is synthesized by reductive amination. In the above reaction, p-methylaniline reacts with ${\text{CH}}_3{\text{CHO, NaBH}}_{\text{3}}\text{CN}$ to form the final product.

Conclusion

The product formed by the reaction of p-methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ with ${\text{CH}}_3{\text{CHO, NaBH}}_{\text{3}}\text{CN}$ is shown in Figure 10.