What are Ambidentate Nucleophiles ?
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An ambident nucleophile is an anionic nucleophile whose negative charge is delocalized by resonance over two unlike atoms or over two like but non-equivalent atoms. The most common ambident nucleophiles are enolate ions. For example, the resonance forms of acetone enolate are shown below.
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The nucleophiles that can attack through two different sites are known as ambident nucleophiles.
For example, cyanide ion is an ambident nucleophile. It can attack through either C atom or N atom to form alkyl cyanide or alkyl isocyanide
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