Treatment of ethyl isobutyrate with ethoxide in ethanol

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1. Treatment of ethyl isobutyrate with ethoxide in ethanol, followed by mild acidic workup, leads to recovery of starting material rather than a Claisen Condensation product. Please explain this observation, using structures rather than words as much as possible.

2. The Wieland-Miescher ketone is an important starting point for the synthesis of biologically active steroid derivatives. It is prepared via a reaction called the Robinson Annulation (which tends to show up on the MCAT). Please provide a detailed arrow-pushing mechanism for this reaction.

Reference no: EM13171158

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