[Diana.1993]

Hey, today I synthesised cyclopropane cyanide from 4-chlorobutyronitrile with t-BuOK and tomorrow im supposed to synthesise the cyclopropane carboxylic acid(from the cyclopropane cyanide from today  with Naoh)

I understand that the t-BuOK Will deprotonate the chlorobutyronitrile and form a carbanion with a negative chargé on the carbon adjacent to the cl.

The carbanion formed is reactive and Will cyclize to give us the cyclopropane.. but what i dont understand is mechanism-wise how the cyclization occurs.. and in what way Does the leaving group leave (cl-)

I would be grateful if anyone could help xx

[Dan]

I understand that the t-BuOK Will deprotonate the chlorobutyronitrile and form a carbanion with a negative chargé on the carbon adjacent to the cl.

Are you sure about that? Which is the most acidic H in 4-chlorobutyronitrile?