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 alkoxides . Deprotonation gives a nucleophilic enolate , which can further react, ., 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 (., alkyl halide ), and is subsequently decarboxylated. Another variation is the Fráter–Seebach alkylation .