Which of the following organic compounds show Carbylamine test?

A. Ethanamine

B. N-Ethylethanamine

C. N,N-Dimethylethanamine

D. Aniline

E. N-Methyl aniline

Choose the correct answer from the options given below:

A, D only

The correct answer is option 3.  A, D only.

Carbylamine reaction includes the addition of amine to the intermediate created from the dehydrohalogenation of chloroform. This intermediate is called dichlorocarbene. The carbylamine reaction is also known as Hofmann isocyanide synthesis. It is the reaction of a primary amine, chloroform and a base to synthesize isocyanides. The dichlorocarbene intermediate is very important for this conversion. The carbylamine reaction cannot be used to synthesize isocyanides from secondary or tertiary amines. In general, the carbylamine reaction can be written as –

\(R-NH_2 + CHCl_3 + 3KOH \longrightarrow \underset{Carbylamine}{RNC} + 3KCl + 3H_2O\)

A. Ethanamine: Since it is an aliphatic primary amine it will undergo carbylamine test

B. N-Ethylethanamine: It is a secondary amine and will not undergo carbylamine test.

C. N, N-Dimethylethanamine: It is a tertiary amine and will not undergo carbylamine test. 

D. Aniline: Since it is an aromatic primary amine it will undergo carbylamine test.

E. N-Methylethanamine: It is a secondary amine and will not undergo carbylamine test. 

Thus only A and D will undergo Carbylamine test.