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Nucleophiles

A nucleophile is an electron pair donor. It has a lone pair of electrons that it can donate to form a new dative covalent bond.Nucleophiles are electron-rich. They are either negatively charged ions, such as OH- and CN-, or neutral molecules with a lone pair, such as NH3 and H2O.Nucleophiles attack atoms that are electron deficient, such as positive ions or the δ+ carbon in a polar bond.For example, the δ+ carbon in the C-X bond of a halogenoalkane is attacked in nucleophilic substitution, and the δ+ carbon in the C=O group of a carbonyl compound is attacked in nucleophilic addition.

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Specification: OCR Chemistry A (H432), A-level, 4.2.2 Haloalkanes. Topic: Reactions and Reactive Species.

Key terms in this lesson

nucleophilic substitution
A reaction mechanism in which a nucleophile donates a lone pair of electrons to an electron-deficient carbon atom, displacing a leaving group.
nucleophilic addition
A reaction mechanism in which a nucleophile donates a lone pair of electrons to the electron-deficient carbon atom of a pi bond, without any group being displaced.

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