Which of the following is/are ambident nucleophiles?

$^{-} C \equiv N$

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$N O_{2}^{-}$

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$P C l_{5}$

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$S n C l_{4}$

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Solution

The correct options are
A
$^{-} C \equiv N$

B
$N O_{2}^{-}$

Nucleophilic reagent or nucleophile: Negatively charged species or a neutral molecule with lone pair of electron, i.e., with electron-rich centre. They act as Lewis base.

$E x a m p l e s :$ $⊖ O H, ⊖ O R, ⊖ C N, ⊖ N H_{2}, ⊖ H (h y d r i d e i o n), H S_{3}, C O ⊖ O$

$R - C \equiv ⊖ C, ⊖ C H (C O O E t)_{2}, C H_{3}, ⊖ C O C H_{2}, H_{2} . . O :, . . R O H . .$

$R - . . O . . - R, R - . . S . . - H, R - . . N H_{2}, . . N H_{3}$

$* R M g X, * R L i, L i A l_{4}$

(Star indicates the atom that donates electron to the substrate.)

And what do you mean by ambident nucleophiles?
Ambident nucleophile: Species having two nucleophilic centres, of which ,one is neutral (complete octet and has at least one lone pair of electorns) and the other is charged (negative charge).

$⊖ C \equiv . . N, ⊖ O - . . N = O, ⊖ O - O ↑ S ↓ O - O H$

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