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Aliphatic primary amines reaction with nitrous acid mechanism

Answer»

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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