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Nucleophilic addition
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===Addition to carbonyl groups=== With a carbonyl compound as an electrophile, the nucleophile can be:<ref name=March /> * [[water]] in [[Hydration reaction|hydration]] to a [[geminal]] [[diol]] (hydrate) * an [[Alcohol (chemistry)|alcohol]] in [[acetalisation]] to an [[acetal]] * a [[hydride]] in [[reducing agent|reduction]] to an [[Alcohol (chemistry)|alcohol]] * an [[amine]] with formaldehyde and a carbonyl compound in the [[Mannich reaction]] * an [[enolate ion]] in an [[aldol reaction]] or [[Baylis–Hillman reaction]] * an [[organometallic]] [[nucleophile]] in the [[Grignard reaction]] or the related [[Barbier reaction]] or a [[Reformatskii reaction]] * [[ylide]]s such as a [[Wittig reagent]] or the [[Corey–Chaykovsky reagent]] or α-silyl carbanions in the [[Peterson olefination]] * a phosphonate carbanion in the [[Horner–Wadsworth–Emmons reaction]] * a pyridine zwitterion in the [[Hammick reaction]] * an [[acetylide]] in [[alkynylation]] reactions. * a [[cyanide ion]] in [[cyanohydrin reaction]]s In many nucleophilic reactions, addition to the carbonyl group is very important. In some cases, the C=O [[double bond]] is [[Organic redox reaction|reduced]] to a C-O [[single bond]] when the nucleophile bonds with carbon. For example, in the cyanohydrin reaction a cyanide ion forms a [[Carbon–carbon bond|C-C bond]] by breaking the carbonyl's double bond to form a [[cyanohydrin]].
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