What happens when benzene diazonium chloride is treated with potassium...
By treating diazonium salts with cuprous cyanide or KCN and copper powder it forms aryl nitrile. Illustrative is the preparation of benzonitrile using the reagent cuprous cyanide: C
H
N
+ CuCN → C
H
CN + Cu+ + N
.
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Reaction Overview
When benzene diazonium chloride (C6H5N2Cl) is treated with potassium cyanide (KCN) in the presence of copper powder (Cu), a significant reaction occurs that leads to the formation of benzonitrile (C6H5CN). This reaction is a classic example of nucleophilic substitution.
Mechanism of Reaction
- Formation of Benzene Diazonium Ion: Benzene diazonium chloride is generated from an aromatic amine and nitrous acid. This ion is highly reactive and can undergo various transformations.
- Nucleophilic Attack: In the presence of KCN, the cyanide ion (CN-) acts as a nucleophile. It attacks the positively charged nitrogen in the diazonium ion, resulting in the displacement of the nitrogen gas (N2), which is a stable and inert product.
- Formation of Benzonitrile: The final product of this reaction is benzonitrile, where the cyanide group replaces the diazonium moiety on the benzene ring. The overall reaction can be summarized as:
Benzene Diazonium Ion + CN- → Benzonitrile + N2
Significance of Copper Powder
- Copper's Role: Copper powder acts as a catalyst in this reaction, facilitating the transformation of the diazonium ion and ensuring the reaction proceeds smoothly.
Conclusion
The treatment of benzene diazonium chloride with potassium cyanide in the presence of copper powder ultimately produces benzonitrile, making option 'D' the correct answer. This reaction showcases the utility of diazonium salts in organic synthesis, particularly in forming nitriles from aromatic compounds.