Answers to the Exercises "SN/E Competition"
With sodium cyanide, an reaction would most likely occur. Due to the stabilization through three alkyl substituents, the tert-butyl carbenium ion is easily produced. Consequently, the reaction depicts a unimolecular mechanism with an intermediate carbenium ion. The cyanide anion is a good nucleophile. In addition, cyanide is merely a weak base. Consequently, an E2 elimination through the abstraction of the β proton by a strong base in the early phase of the reaction can virtually never take place.