Chapter 25, Problem 25.29P

Interpretation Introduction

(a)

Interpretation: The product formed by the treatment of given compound with ${\text{NaNO}}_{\text{2}}$ and $\text{HCl}$ is to be drawn.

Concept introduction: Primary and secondary amines on reaction with ${\text{NaNO}}_{\text{2}}$ in the presence of $\text{HCl}$ yield different products. Diazonium salt is formed by the reaction of primary amine with ${\text{NaNO}}_{\text{2}}+\text{HCl}$ whereas N-nitrosamine is formed by the reaction of secondary amine with ${\text{NaNO}}_{\text{2}}+\text{HCl}$.

Answer to Problem 25.29P

The product formed by the treatment of given compound with ${\text{NaNO}}_{\text{2}}$ and $\text{HCl}$ is shown below.

Explanation of Solution

Primary and secondary amines on reaction with ${\text{NaNO}}_{\text{2}}$ in the presence of $\text{HCl}$ yield different products. Diazonium salt is formed by the reaction of primary amine with ${\text{NaNO}}_{\text{2}}+\text{HCl}$ whereas N-nitrosamine is formed by the reaction of secondary amine with ${\text{NaNO}}_{\text{2}}+\text{HCl}$.

In the given compound, nitrogen atom is substituted by two hydrogen atoms and one phenyl group. Hence, it is a primary amine. Therefore, the product formed by the reaction of given compound with ${\text{NaNO}}_{\text{2}}$ and $\text{HCl}$ is aryl diazonium salt as shown in Figure 1.

Figure 1

Conclusion

The product formed by the treatment of given compound with ${\text{NaNO}}_{\text{2}}$ and $\text{HCl}$ is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: The product formed by the treatment of given compound with ${\text{NaNO}}_{\text{2}}$ and $\text{HCl}$ is to be drawn.

Concept introduction: Primary and secondary amines on reaction with ${\text{NaNO}}_{\text{2}}$ in the presence of $\text{HCl}$ yield different products. Diazonium salt is formed by the reaction of primary amine with ${\text{NaNO}}_{\text{2}}+\text{HCl}$ whereas N-nitrosamine is formed by the reaction of secondary amine with ${\text{NaNO}}_{\text{2}}+\text{HCl}$.

Answer to Problem 25.29P

The product formed by the treatment of given compound with ${\text{NaNO}}_{\text{2}}$ and $\text{HCl}$ is shown below.

Explanation of Solution

Primary and secondary amines on reaction with ${\text{NaNO}}_{\text{2}}$ in the presence of $\text{HCl}$ yield different products. Diazonium salt is formed by the reaction of primary amine with ${\text{NaNO}}_{\text{2}}+\text{HCl}$ whereas N-nitrosamine is formed by the reaction of secondary amine with ${\text{NaNO}}_{\text{2}}+\text{HCl}$.

In the given compound, nitrogen atom is substituted by one hydrogen atom and two alkyl groups. Hence, it is a secondary amine. Therefore, the product formed by the reaction of given compound with ${\text{NaNO}}_{\text{2}}$ and $\text{HCl}$ is N-nitrosamine as shown in Figure 2.

Figure 2

Conclusion

The product formed by the treatment of given compound with ${\text{NaNO}}_{\text{2}}$ and $\text{HCl}$ is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation: The product formed by the treatment of given compound with ${\text{NaNO}}_{\text{2}}$ and $\text{HCl}$ is to be drawn.

Concept introduction: Primary and secondary amines on reaction with ${\text{NaNO}}_{\text{2}}$ in the presence of $\text{HCl}$ yield different products. Diazonium salt is formed by the reaction of primary amine with ${\text{NaNO}}_{\text{2}}+\text{HCl}$ whereas N-nitrosamine is formed by the reaction of secondary amine with ${\text{NaNO}}_{\text{2}}+\text{HCl}$.

Answer to Problem 25.29P

The product formed by the treatment of given compound with ${\text{NaNO}}_{\text{2}}$ and $\text{HCl}$ is shown below.

Explanation of Solution

Primary and secondary amines on reaction with ${\text{NaNO}}_{\text{2}}$ in the presence of $\text{HCl}$ yield different products. Diazonium salt is formed by the reaction of primary amine with ${\text{NaNO}}_{\text{2}}+\text{HCl}$ whereas N-nitrosamine is formed by the reaction of secondary amine with ${\text{NaNO}}_{\text{2}}+\text{HCl}$.

In the given compound, nitrogen atom is substituted by one hydrogen atom and two alkyl groups. Hence, it is a secondary amine. Therefore, the product formed by the reaction of given compound with ${\text{NaNO}}_{\text{2}}$ and $\text{HCl}$ is N-nitrosamine as shown in Figure 3.

Figure 3

Conclusion

The product formed by the treatment of given compound with ${\text{NaNO}}_{\text{2}}$ and $\text{HCl}$ is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation: The product formed by the treatment of given compound with ${\text{NaNO}}_{\text{2}}$ and $\text{HCl}$ is to be drawn.

Concept introduction: Primary and secondary amines on reaction with ${\text{NaNO}}_{\text{2}}$ in the presence of $\text{HCl}$ yield different products. Diazonium salt is formed by the reaction of primary amine with ${\text{NaNO}}_{\text{2}}+\text{HCl}$ whereas N-nitrosamine is formed by the reaction of secondary amine with ${\text{NaNO}}_{\text{2}}+\text{HCl}$.

Answer to Problem 25.29P

The product formed by the treatment of given compound with ${\text{NaNO}}_{\text{2}}$ and $\text{HCl}$ is shown below.

Explanation of Solution

Primary and secondary amines on reaction with ${\text{NaNO}}_{\text{2}}$ in the presence of $\text{HCl}$ yield different products. Diazonium salt is formed by the reaction of primary amine with ${\text{NaNO}}_{\text{2}}+\text{HCl}$ whereas N-nitrosamine is formed by the reaction of secondary amine with ${\text{NaNO}}_{\text{2}}+\text{HCl}$.

In the given compound, nitrogen atom is substituted by two hydrogen atoms and one alkyl group. Hence, it is a primary amine. Therefore, the product formed by the reaction of given compound with ${\text{NaNO}}_{\text{2}}$ and $\text{HCl}$ is alkyl diazonium salt as shown in Figure 4.

Figure 4

Conclusion

The product formed by the treatment of given compound with ${\text{NaNO}}_{\text{2}}$ and $\text{HCl}$ is shown in Figure 4.