Question

What is an ambident nucleophile? Give one example.

Hint:

Other examples of ambident nucleophiles include \( NO_2^- \) and enolate ions.

Answer 1

Step 1: Ambident nucleophiles have two nucleophilic sites, and can attack through either site.
Step 2: For example, the cyanide ion (\( CN^- \)) can attack through carbon to form alkyl cyanides, or through nitrogen to form isocyanides.
\[ R{-}Br + CN^- \longrightarrow R{-}CN \quad \text{or} \quad R{-}NC \] Step 3: The actual product depends on the conditions of the reaction and the nature of the substrate.