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During qualitative organic analysis, an unknown amine is treated with a cold mixture of and (LibermaAmines Chemistry Question

Question

During qualitative organic analysis, an unknown amine is treated with a cold mixture of $NaNO_2$ and $HCl$ (Libermann's nitroso reaction). A distinct, heavy yellow oily liquid rapidly separates from the aqueous phase. What is the structural classification of this amine?

Answer: B

💡 Solution & Explanation

Both aliphatic and aromatic secondary ($2^\circ$) amines lack the necessary hydrogen atoms to form diazonium species. Instead, they react cleanly with nitrous acid to form extremely characteristic, water-insoluble N-nitrosamines ($R_2N-N=O$), which physically present as distinct yellow oily liquids.

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