tert-butylaminetert-butylamine cannot be prepared

Question

Tert-butylamine

Tert-butylamine cannot be prepared by the Gabriel synthesis because it would require that the nitrogen of phthalimide be alkylated with tert-butyl bromide in an SN₂ reaction.  Tertiary alkyl halides generally do not undergo SN₂ reactions but, under basic conditions, undergo E₂ reactions instead.