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Exercise · Q6

Q.An unknown nitro compound, on reduction with Sn/HCl\text{Sn}/\text{HCl}, gives a primary aromatic amine that forms a stable diazonium salt at 00–5∘C5^\circ\text{C}. What was the starting nitro compound, and what general class of reaction converted it to the amine?

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✓ Free question

Only a primary AROMATIC amine forms a diazonium salt stable enough to exist at 00–5∘C5^\circ\text{C} (Section 25.9/25.14) -- an aliphatic primary amine's diazonium salt decomposes instantly even in the cold. So the amine formed on reduction must have been aromatic, meaning the nitro compound reduced was an aromatic nitro compound -- nitrobenzene, reduced by a full reducing system such as Sn/HCl\text{Sn}/\text{HCl}, Fe/HCl\text{Fe}/\text{HCl} or catalytic hydrogenation, to give aniline.

✓Final answer

Nitrobenzene, reduced to aniline by a complete metal-acid or catalytic reduction.

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