JEE Main · 2021 · 17 Mar 2021 · Shift 2 · General Organic Chemistry

An ambident nucleophile has two different donor atoms through which it can attack. The cyanide ion is a resonance hybrid carrying a lone pair on carbon and on nitrogen, so the ionic potassium salt gives attack through carbon to form a nitrile while the largely covalent silver salt gives attack through nitrogen to form an isocyanide. The nitrite ion has donor sites at nitrogen and at oxygen in the same way, giving a nitroalkane with the silver salt and an alkyl nitrite with the potassium salt. A carboxylate has two equivalent oxygens and no second kind of donor atom, and iodide has a single donor atom, so neither is ambident. The ambident pairs are $AgCN/KCN$ and $\mathrm{AgN}{\mathrm{O}}_2/KN{\mathrm{O}}_2$.