Question

Which compounds give carbylamine reaction?

Answer 1

Carbylamine reaction:

• “The carbylamine reaction is the synthesis of an isocyanide by the reaction of a primary amine, chloroform, and base”.
• When aliphatic or aromatic primary amines are heated along with chloroform and alcoholic potassium hydroxide, a carbylamine is formed and the reaction is known as a carbylamine reaction.
• The chemical reaction can be depicted as:

$$\begin{gathered} \mathrm{R}-{\mathrm{NH}}_2+{\mathrm{CHCl}}_3+3\mathrm{KOH}(\mathrm{alc}.)\stackrel{∆}{\to }\mathrm{R}-\mathrm{NC}+3\mathrm{KCl}+{\mathrm{H}}_2\mathrm{O} \\ \mathrm{Primary}\mathrm{amine}\mathrm{Carbylamine} \end{gathered}$$

Example of Carbylamine reaction:

• When methamine is heated with alcoholic potassium hydroxide and chloroform, methylcarbylamine is formed along with by-products.
• The chemical reaction can be depicted as:
• $$\begin{gathered} {\mathrm{CH}}_3{\mathrm{NH}}_2+{\mathrm{CHCl}}_3+3\mathrm{KOH}(\mathrm{alc}.)\stackrel{∆}{\to }{\mathrm{CH}}_3-\mathrm{NC}+3\mathrm{KCl}+{\mathrm{H}}_2\mathrm{O} \\ \mathrm{Methamine}\mathrm{Methyl}\mathrm{carbylamine} \end{gathered}$$

The compound which gives carbylamine reaction:

• Primary amines will give carbylamine reaction.