(a) Draw a stepwise mechanism for the reaction of ethyl 2,4-hexadienoate with diethyl

Chapter 24, Problem 24.59

(choose chapter or problem)

(a) Draw a stepwise mechanism for the reaction of ethyl 2,4-hexadienoate with diethyl oxalate in the presence of base. (b) How does your mechanism explain why a new carboncarbon bond forms on C6? (c) Why is this reaction an example of a crossed Claisen reaction? + + O CO2Et ethyl 2,4-hexadienoate (CO2Et)2 diethyl oxalate EtOH CO2Et EtO2C EtOH NaOEt

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