Ambident nucleophiles are nucleophiles having two nucleophilic sites. Thus, ambident nucleophiles have two sites through which they can attack. For example, nitrite ion is an ambident nucleophile.
Nitrite ions can attack through oxygen resulting in the formation of alkyl nitrites. Also, it can attack through nitrogen resulting in the formation of nitroalkanes.
A compound (A) with molecular formula $C_4H_9I$ which is a primary alkyl halide, reacts with alcoholic KOH to give compound (B). Compound (B) reacts with HI to give (C) which is an isomer of (A). When (A) reacts with Na metal in the presence of dry ether, it gives a compound (D), C8H18, which is different from the compound formed when n-butyl iodide reacts with sodium. Write the structures of A, (B), (C) and (D) when (A) reacts with alcoholic KOH.
