Question

Cyanide ion acts as an ambident nucleophile. From which end it acts as a stronger nucleophile in aqueous medium?

• A. It acts as a stronger nucleophile from carbon end
• B. It acts as a stronger nucleophile from nitrogen end
• C. It depends on the nature of the alkyl halide.
• D. It has same strength from both the ends

Answer 1

The correct option is A It acts as a stronger nucleophile from carbon end

Cyanide is an ambident nucleophile as it can react either through C or N. Here, $C{N}^{-}$ exist as free ions in solution and so C site is more nucleophilic than N site and available to attack the carbon to form alkyl cyanides.
$R-X+C{N}^{-}\to R-C\equiv N+X^{-}$