Formation of Alcohols From Primary Amines

$$\text{R--NH}_2 + \text{HNO}_2 \ (\text{NaNO}_2 + \text{HCl}) \to \text{R--OH} + \text{N}_2\uparrow + \text{H}_2\text{O}$$

Concept: Primary aliphatic amines react with nitrous acid ($$\text{HNO}_2$$, generated in situ using $$\text{NaNO}_2$$ and dilute $$\text{HCl}$$) to form highly unstable aliphatic diazonium salts. These instantly decompose to yield nitrogen gas, a carbocation intermediate, and a mixture of alcohol products upon reaction with water.