Editing Ester (section)

===Other ester reactivities===
Esters react with nucleophiles at the carbonyl carbon.<ref>{{March6th|page=1453}}</ref> The carbonyl is weakly electrophilic but is attacked by strong nucleophiles (amines, alkoxides, hydride sources, organolithium compounds, etc.). The C–H bonds adjacent to the carbonyl are weakly acidic but undergo deprotonation with strong bases. This process is the one that usually initiates condensation reactions. The carbonyl oxygen in esters is weakly basic, less so than the carbonyl oxygen in amides due to resonance donation of an electron pair from nitrogen in amides, but forms [[adduct]]s.

As for [[aldehydes]], the hydrogen atoms on the carbon adjacent ("α to") the carboxyl group in esters are sufficiently acidic to undergo deprotonation, which in turn leads to a variety of useful reactions. Deprotonation requires relatively strong bases, such as [[alkoxide]]s. Deprotonation gives a nucleophilic [[enolate]], which can further react, e.g., the [[Claisen condensation]] and its intramolecular equivalent, the [[Dieckmann condensation]]. This conversion is exploited in the [[malonic ester synthesis]], wherein the diester of [[malonic acid]] reacts with an electrophile (e.g., [[alkyl halide]]), and is subsequently decarboxylated. Another variation is the [[Fráter–Seebach alkylation]].