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Question:
Write two examples for ambident nucleophiles.
Answer:

Following are the examples of ambident nucleophiles.

1. The resonance forms of acetone enolate.

 

ambidentnucleophile1.png

 The hybrid of the two figures shown above is as follows -

ambidentnucleophile2.png

 

2. The resonance hybrid of thiocyanate ion, SCN−.

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Both the S and the C atoms can act as nucleophiles.

So, the SN2 reaction of an alkyl halide with SCN often leads to a mixture of an alkyl thiocyanate and an alkyl isothiocyanate.

 

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