How do aliphatic primary amines react with nitrous acid?

When aliphatic primary amines react with nitrous acid (HNO₂), they undergo a complex process that converts them into nitrogen gas and a mixture of alkenes and alcohols corresponding to the alkyl group.1

This reaction proceeds through the formation of an unstable aliphatic diazonium salt, which exists only as a transient intermediate before quickly decomposing into a nitrogen molecule and a carbonium ion. Because of this rapid decomposition, the reaction is distinct from the behavior of aromatic primary amines, which can form stable diazonium salts when kept at low temperatures (typically 0 °C).21

This chemical process has historically been utilized for the analytical determination of primary amino groups in a procedure known as the Van Slyke method.1