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Chapter 6: Problem 145

Identify the reactions in which both the nitrogen atoms of benzene diazonium chloride are retained in the product. (a) Reduction with zinc and hydrochloric acid (b) Reduction with \(\mathrm{SnCl}\), and hydrochloric acid (c) Reduction with sodium sulphite (d) Coupling reaction

Short Answer

Expert verified
The reactions that retain both nitrogen atoms of benzene diazonium chloride in the product are (c) reduction with sodium sulfite and (d) coupling reaction.

Step by step solution

01

Write the structure of benzene diazonium chloride

The structure of benzene diazonium chloride is given by: \[C_6H_5N_2Cl\] Now, we will consider each reaction one by one to check if both nitrogen atoms are retained in the product or not.
02

Reduction with zinc and hydrochloric acid

The reaction of benzene diazonium chloride with zinc and hydrochloric acid is given by: \[C_6H_5N_2Cl + Zn + 2HCl \rightarrow C_6H_5NH_2 + ZnCl_2 + N_2\] In this reaction, \(N_2\) is released as a product, indicating that both nitrogen atoms are not retained in the product.
03

Reduction with \(\mathrm{SnCl}\) and hydrochloric acid

The reaction of benzene diazonium chloride with \(\mathrm{SnCl}\) and hydrochloric acid is given by: \[C_6H_5N_2Cl + SnCl_2 + 3HCl \rightarrow C_6H_5Cl + SnCl_4 + 2NH_4Cl\] In this reaction, two nitrogen atoms are transferred to form ammonium chloride (\(NH_4Cl\)). Thus, in this reaction, both nitrogen atoms are not retained in the product.
04

Reduction with sodium sulfite

The reaction of benzene diazonium chloride with sodium sulfite is given by: \[C_6H_5N_2Cl + Na_2SO_3 \rightarrow C_6H_5N=N-SO_3Na + NaCl\] In this reaction, both nitrogen atoms are retained in the product as a part of the azo group (\(N=N\)). So, this reaction retains both nitrogen atoms in the product.
05

Coupling reaction

In a coupling reaction, the benzene diazonium chloride reacts with nucleophiles such as phenols or anilines. The general reaction is given by: \[C_6H_5N_2Cl + Nucleophile \rightarrow C_6H_5N=N-Nucleophile + HCl\] In coupling reactions, both nitrogen atoms are retained in the product as part of the azo group (\(N=N\)). So, coupling reactions retain both nitrogen atoms in the product. From the analysis of all four reactions, only (c) reduction with sodium sulfite and (d) coupling reaction retain both nitrogen atoms in their respective products.

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