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Question

Which among the following species is an ambident nucleophile?


A

CH3CΘH2

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B

CH2=CH2

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C

θCN

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D

¨NH3

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Solution

The correct option is

C

θCN

Ambident nucleophiles are nucleophiles having two nucleophilic sites. Thus, ambident nucleophiles have two sites through which they can attack.

For example, cyanide ion is an ambident nucleophile. It can attack through either the C atom or N atom to form alkyl cyanide or alkyl isocyanide.

Both carbon and nitrogen can donate electron pairs in cyanide ion.


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