Q14 of 46 Page 1

Define ambident nucleophile with an example.

It is an anionic molecule in which the negative charge is in delocalization with two unlike atoms. For example, the enolate ion,


The negative charge is between a carbon atom and an oxygen atom. Another example can be considered as an the cyanide ion



When in acidic conditions, the negative charge is balanced by H+ ion and thus the attacking atom is nitrogen, while in basic or neutral medium the attacking site is carbon atoms. Thus it can also be stated that, ‘ambident nucleophiles have two active sites for reaction’.


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