The addition of diethyl malonate to benzaldehyde in the presence of the basic amine piperidine gives the unsaturated diester, diethyl 2-benzylidenemalonate. This is an example of the Knoevenagel reaction, a synthetically useful carbonyl condensation reaction, which is related to the aldol condensation.
(a) What is the nucleophile in the Knoevenagel reaction?
(b) The unsaturated diester A in part (c) was prepared by a Knoevenagel reaction and used to synthesize the anticonvulsant drug gabapentin. From which two reactants is the diester synthesized?
(c) Fill in the missing reagents in the reaction scheme.
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