aliphatic primary amines reaction with nitrous acid mechanism
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Nitrous acid ( HNO2 or HONO ) reacts with aliphatic amines in a fashion that provides a useful test for distinguishing primary, secondary and tertiary amines.
1°-Amines + HONO (cold acidic solution) → Nitrogen Gas Evolution from a Clear Solution
2°-Amines + HONO (cold acidic solution) → An Insoluble Oil (N-Nitrosamine)
3°-Amines + HONO (cold acidic solution) → A Clear Solution (Ammonium Salt Formation)
Nitrous acid is a Brønsted acid of moderate strength (pKa = 3.3).
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❥The reaction of aliphatic primary amines with nitrous acid gives aromatic diazonium salts which decompose to form a mixture of compounds containing alkyl chlorides, alkenes and alcohols. Usually, alcohols are the major products.
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