Question

In carbylamine reaction, primary amines react with alkaline $CHC{l}_3$ and the final product is a carbylamine. From start to finish, how many instances of dehydrochlorination takes place?

Answer 1

Lets take an example of aniline.
First dehydrohalogenation appears in formation of dichlorocarbene and twice it occurs in formation of isocyanide.
So a total of three instances of dehydrohalogenation takes place.