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Example · Example 35

Q.Aniline is treated with NaNO2\text{NaNO}_2 and dilute HCl\text{HCl} at 00–5∘C5^\circ\text{C} (diazotization). Write the equation for the formation of benzenediazonium chloride and explain why the low temperature is essential.

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NaNO2\text{NaNO}_2 and HCl\text{HCl} generate nitrous acid in situ, which diazotizes aniline's free −NH2-\text{NH}_2 group to the diazonium salt: C6H5NH2+NaNO2+2HCl→0–5∘CC6H5N2+ Cl−+NaCl+2H2O\text{C}_6\text{H}_5\text{NH}_2 + \text{NaNO}_2 + 2\text{HCl} \xrightarrow{0\text{–}5^\circ\text{C}} \text{C}_6\text{H}_5\text{N}_2^+\ \text{Cl}^- + \text{NaCl} + 2\text{H}_2\text{O}. Even though the aromatic diazonium ion is stabilised relative to an aliphatic one by resonance delocalisation of its charge into the ring, it is still a comparatively reactive species that decomposes (largely by hydrolysis to phenol, with loss of N2\text{N}_2) if the temperature …

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