Aniline in a set of reactions yielded a product D.

The structure of the product D would be:

Question

Which of the following reactions will not give a primary amine?

Answer 1

Let's analyze the sequence of reactions starting from aniline (C_6H_5NH_2).
The first reaction involves NaNO₂/HCl, which converts aniline to a diazonium salt. This step is represented as follows:
C_6H_5NH_2 + NaNO_2 + HCl \rightarrow C_6H_5N_2^+Cl^− + H_2O + NaCl
The product formed is benzene diazonium chloride.
The second reaction with CuCN converts the diazonium salt into cyanobenzene (C_6H_5CN):
C_6H_5N_2^+Cl^− + CuCN \rightarrow C_6H_5CN + N_2 + CuCl
The next step involves the reduction of the cyano group using H₂/Ni to form benzylamine (C_6H_5CH_2NH_2):
C_6H_5CN + 2H_2 \rightarrow C_6H_5CH_2NH_2
However, in this series of reactions, this is incorrect according to the provided image.
The final step involves reacting the product with HNO₂ to replace the amino group with a hydroxyl group, forming benzyl alcohol (C_6H_5CH_2OH):
C_6H_5CH_2NH_2 + HNO_2 \rightarrow C_6H_5CH_2OH + N_2 + H_2O

The series of reactions thus results in the formation of benzyl alcohol. Therefore, the structure of product D is C₆H₅CH₂OH.

Other options represent different chemical structures that are not formed in this specific series of reactions.

Answer 2

Let's analyze the sequence of reactions starting from aniline (C_6H_5NH_2).
The first reaction involves NaNO₂/HCl, which converts aniline to a diazonium salt. This step is represented as follows:
C_6H_5NH_2 + NaNO_2 + HCl \rightarrow C_6H_5N_2^+Cl^− + H_2O + NaCl
The product formed is benzene diazonium chloride.
The second reaction with CuCN converts the diazonium salt into cyanobenzene (C_6H_5CN):
C_6H_5N_2^+Cl^− + CuCN \rightarrow C_6H_5CN + N_2 + CuCl
The next step involves the reduction of the cyano group using H₂/Ni to form benzylamine (C_6H_5CH_2NH_2):
C_6H_5CN + 2H_2 \rightarrow C_6H_5CH_2NH_2
However, in this series of reactions, this is incorrect according to the provided image.
The final step involves reacting the product with HNO₂ to replace the amino group with a hydroxyl group, forming benzyl alcohol (C_6H_5CH_2OH):
C_6H_5CH_2NH_2 + HNO_2 \rightarrow C_6H_5CH_2OH + N_2 + H_2O

The series of reactions thus results in the formation of benzyl alcohol. Therefore, the structure of product D is C₆H₅CH₂OH.

Other options represent different chemical structures that are not formed in this specific series of reactions.

The Correct Option is D