Question

Cyanide anion has two atoms that have lone pair of electrons. Either could act as nucleophile in the reaction. Yet in the vast majority of the cases, carbon acts as nucleophile and forms a bond to the substrate why?

• A. Nitrogen is strongly solvated in hydroxylic sovents. It will be less reactive
• B. Carbon is more reactive in polar aprotic solvents, normally used for these $S_{N}2$ reaction
• C. Carbon site is more nucleophilic than Nitrogen site
• D. The lone pair of electrons on C is in sp hybrid orbital

Answer 1

The correct option is C Carbon site is more nucleophilic than Nitrogen site


Both carbon and nitrogen are capable of donating electron pair but C site is more nucleophilic than N site and readily available to attack the alkylhalide​.