Animated Solution for Chemistry - Organic Chemistry: On heating an aliphatic primary amine with chloroform and ethanolic potassium hydroxide, the organic compound formed is

Imagine walking into a chemistry lab and being hit by an incredibly distinct, pungent, and foul odor. Chances are, someone is performing the Carbylamine reaction. This reaction is not just a chemical transformation; it is a sensory experience that chemists use as a definitive test for a specific class of compounds.

Let's break down the reactants provided in our problem. We are given an aliphatic primary amine ($R-N{H}_2$), chloroform ($CHC{l}_3$), and ethanolic potassium hydroxide ($KOH$).

When these three ingredients are mixed and heated, they set the stage for a classic named reaction. The strong base, ethanolic $KOH$, reacts with chloroform to generate a highly reactive intermediate known as dichlorocarbene ($:CC{l}_2$). This intermediate is the secret key that unlocks the rest of the reaction.

The dichlorocarbene eagerly attacks the electron-rich nitrogen atom of the primary amine. After a series of rapid steps involving the loss of protons and chloride ions, the transformation is complete.

The overall chemical equation can be written as:

Notice what happened to the amine group. The $-N{H}_2$ group has been completely transformed into an $-NC$ group.

This newly formed functional group, $-NC$, is known as an isocyanide or carbylamine. It is this exact compound that is responsible for the terrible smell we mentioned earlier!

Therefore, heating an aliphatic primary amine with chloroform and ethanolic potassium hydroxide yields an alkyl isocyanide. This makes the Carbylamine reaction an excellent qualitative test, as secondary and tertiary amines simply cannot undergo this transformation.