Editing Nucleophilic addition (section)

== Addition to carbon–carbon double bonds ==
When a [[nucleophile]] X<sup>−</sup> adds to an [[alkenes|alkene]], the driving force is the transfer of negative charge from X to the electron-poor [[Saturated and unsaturated compounds|unsaturated]] -C=C- system.  This occurs through the formation of a [[covalent bond]] between X and one carbon atom, concomitant with the transfer of electron density from the [[pi bond]] onto the other carbon atom (step 1).<ref name=March />  During a [[One-pot synthesis|telescoped second reaction]] or [[Workup (chemistry)|workup]] (step 2), the resulting negatively charged [[carbanion]] combines with an [[Electrophile|electrophilic]] Y to form the second covalent bond.{{cn|date=March 2024}}

:[[Image:NucleophilicAdditionGeneral.svg|300px|Nucleophilic addition to an alkene]]

Unsubstituted and unstrained alkenes are typically insufficiently polar to admit nucleophilic addition, but a few exceptions are known. 

The strain energy in [[fullerene]]s weakens their [[double bond|double-bonds]]; addition thereto is the [[Bingel reaction]].

Bonds adjacent to an [[Electron-withdrawing group|electron-withdrawing]] substituent (e.g. a [[carbonyl group]], [[nitrile]], or [[fluoride]]) readily admit nucleophilic addition.  In this process, [[conjugate addition reaction|conjugate addition]], the nucleophile X adds [[Locant|β]] to the substituent, because then said substituent [[Inductive effect|inductively]] stabilizes the product's negative charge.  [[Aromaticity|Aromatic]] substituents, although typically [[Electrophile|electrophilic]], can also sometimes stabilize negative charge; for example, [[styrene]] reacts in [[toluene]] with [[sodium]] to give 1,3-diphenylpropane:<ref>''Sodium-catalyzed Side Chain Aralkylation of Alkylbenzenes with Styrene'' Herman Pines, Dieter Wunderlich J. Am. Chem. Soc.; 1958; 80(22)6001–6004. {{doi|10.1021/ja01555a029}}</ref>