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Question

Which of the following is/are ambident nucleophiles?


A

CN

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B

NO2

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C

PCl5

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D

SnCl4

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Solution

The correct options are
A

CN


B

NO2


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.

Examples:OH,OR,CN,NH2,H (hydride ion), HSO3,COO

RCC,CH(COOEt)2,CH3,COCH2, H2..O:, ..ROH..

R..O..R,R..S..H,R..NH2, ..NH3

R MgX, RLi, LiAlH4

(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..N,O..N=O,OOSOOH


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