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Question

Compound [A] is an aromatic amine which react with NaNO2+HCl at 273278 K and form compound [B]. Compound [B] react with HBF4 and the obtain product on further heating, in the presence of NaNO2 and confirm compound [C]. Compound [C] reduced in the presence of Sn/HCl 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 NaNO2 / HCl at 273-278K gives benzene diazonium chloride. Balz-Schiemann reaction then replaces diazo group with F by treatment with HB4 to obtain fluorobenzene. F atom is then replaced with nitro group by heating with NaNO2. Reduction with Sn/HCl converts nitrobenzene to aniline.
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