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Magazine Chapter 22: Q39P (page 1179)
Propose mechanisms for the two Dieckmann condensations just shown.
Short Answer
Step by step solution
Mechanism of formation of methyl 2-oxocyclohexanecarboxlate by ethoxide ion
Internal 鈥淐laisen condensation or Claisen cyclization鈥欌�� of a diester to form a ring with the elimination of an alkoxide ion is known as Dieckmann condensation or a Dieckmann cyclization.
Diethyl adipate reacts with base ethoxide ion, which abstract alpha-hydrogen from it, forming resonance stabilizedenolate.
The enolate acts as a nucleophile and attacks the second carbonyl carbon of the same diethyl adipate molecule to form the 5-membered ring. Finally, the removal of ethoxide ion form the desired product ethyl 2-oxocyclohexanecarboxlate.
Formation of ethyl 2-oxocyclohexanecarboxlate
Mechanism of formation of methyl 2-oxocyclohexanecarboxlate by methoxide ion
Dimethyl heptanedioate reacts with base methoxide ion, which abstract alpha-hydrogen from it, forming a resonance stabilized enolate.
The enolate attacks the second carbonyl carbon of the same molecule Dimethyl heptanedioate to form the 5-membered ring. Finally, the removal of methoxide ion forms the desired product ethyl 2-oxocyclohexanecarboxlate.
Formation of ethyl 2-oxocyclohexanecarboxlate
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