Question:medium

Which of the following is an ambident nucleophile?

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Other common ambident nucleophiles to remember for exams are $NO_2^-$ (Nitrito/Nitro) and $SCN^-$ (Thiocyanato/Isothiocyanato).
Updated On: Jun 26, 2026
  • $OH^-$
  • $NH_2^-$
  • $I^-$
  • $CH_3O^-$
  • $CN^-$
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The Correct Option is

Solution and Explanation

Step 1: Understanding the Concept:
An ambident nucleophile is a species that possesses two or more nucleophilic centers (atoms with lone pairs) through which it can attack a substrate.
Step 2: Key Formula or Approach:
Identify atoms with lone pairs in each ion. If there are two different types of atoms that can donate electrons, it's ambident.
Step 3: Detailed Explanation:
Cyanide ion (\( CN^- \)) has lone pairs on both the Carbon and Nitrogen atoms.
- If it attacks through Carbon, it forms a Cyanide (\( R-CN \)).
- If it attacks through Nitrogen, it forms an Isocyanide (\( R-NC \)).
Other common examples include \( NO_2^- \) and \( SCN^- \).
OH{-}, I{-}, and Alkoxides have only one effective nucleophilic center.
Step 4: Final Answer:
CN{-} is the ambident nucleophile.
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