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Reaction with Diazonium Salts

Compound [A...

Question

Compound $[A]$ is an aromatic amine which react with $N a N O_{2} + H C l$ at $273 - 278 K$ and form compound $[B]$ . Compound $[B]$ react with $H B F_{4}$ and the obtain product on further heating, in the presence of $N a N O_{2}$ and confirm compound $[C]$ . Compound $[C]$ reduced in the presence of $S n / H C l$ to re-formed compound $[A]$ . Write general name of $^{'} A^{'},^{'} B^{'}$ and $^{'} C^{'}$ and write equation of all reaction involved?

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Solution

Diazotization of aniline with $N a N O_{2}$ / HCl at 273-278K gives benzene diazonium chloride. Balz-Schiemann reaction then replaces diazo group with $- F$ by treatment with $H B_{4}$ to obtain fluorobenzene. F atom is then replaced with nitro group by heating with $N a N O_{2}$ . Reduction with Sn/HCl converts nitrobenzene to aniline.

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