Question

Ketone 1 gives two different bicyclic products depending on the base used: when treated with potassium tert-butoxide at room temperature, it produces ketone 2, while when treated with LDA at low temperatures and then heated, it produces ketone 3. Write arrow-pushing mechanisms for the formation of both 2 and 3 and explain why the reaction conditions favor each product.

1. KOtBu, tBuOH 1. LDA 2. H2O 2. H2O Br

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