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What are ambident nucleophiles? Explain ...

What are ambident nucleophiles? Explain with an example.

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Nucleophiles which can attack through two different sites are called ambident nucleophiles. For example, cyanide ion is a resonance hybrid of the following two structures :
`overset(-):C-=N:harr:C=overset(..)Noverset(-):`
It can attack through carbon to from cyanide and through N to form is ) cyanide.
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