Which of the following is an ambident  nucleophile?

$\mathrm{I}){\mathrm{HSO}}_3^{⊝}$     $\mathrm{II}){\mathrm{CN}}^{⊝}$      III)${\mathrm{NO}}_2^{⊝}$

An ambident nucleophile is a special type of nucleophile that has the capability to initiate nucleophilic attacks from two or more distinct positions within the same molecule or ion. This unique property allows the molecule to participate in chemical reactions through multiple reactive centers.

To analyze the given options:

• HSO₃^⊝: This species is not classified as an ambident nucleophile because it does not have two distinct nucleophilic centers for reactivity.
• CN^⊝: The cyanide ion is a classic example of an ambident nucleophile. It can attack through the carbon atom, acting as a carbon nucleophile, or through the nitrogen atom, functioning as a nitrogen nucleophile.
• NO₂^⊝: The nitrite ion is another well-known example of an ambident nucleophile. It can attack either through the oxygen atom or the nitrogen atom, depending on the reaction conditions and the electrophile involved.

In summary, an ambident nucleophile is characterized by its ability to interact with electrophiles through multiple reactive sites. In the given options, both CN^⊝ and NO₂^⊝ are examples of ambident nucleophiles because they can exhibit reactivity from different atoms within their structure.