Nitrous acid (HNO2 or HONO) reacts with aliphatic amines in a fashion that provides a useful

test for distinguishing primary, secondary and tertiary amines.

In each of the following reactions, the amine would be acidified with hydrochloric acid and a
solution of sodium or potassium nitrite added.
The acid and the nitrite form nitrous acid which then reacts with the amine.

Procedure

1. Prepare sodium nitrite solution.

 Take a small quantity of sodium nitrite in test tube. Add small quantity of distilled
water then the shake test tube to dissolve sodium nitrite in water to get sodium nitrite
solution.
 Cool the sodium nitrite solution in ice bath.
2. Take small quantities of primary, secondary, and tertiary amines in test tubes A, B, and
C respectively
3. Dissolve the given organic compound in concentrated hydrochloric acid.
4. Cool the solution in ice bath.
5. To the cooled solution, add sodium nitrite solution and mix well.

Results
 Primary aliphatic amines react with nitrous acid to give nitrogen gas, which is seen as
bubbles.

 Secondary amines react with nitrous acid to form a yellow oily nitrosamine.
-No gas was evolved

 Tertiary amines react with nitrous acid to form soluble nitrite salts.
-No gas was evolved and no yellow liquid

Reference
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/
Supplemental_Modules_(Organic_Chemistry)/Amines/Reactivity_of_Amines/
Reaction_of_Amines_with_Nitrous_Acid
https://byjus.com/chemistry/test-for-amino-groups/
https://www.chemguide.co.uk/organicprops/amines/nitrousacid.html