Advanced Organic Chemistry Practice Problems 2021 [verified] ⭐ Extended

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The thermodynamic enolate is actually the less substituted enolate (the one at the $\alpha$ carbon not in the ring) because the ring has significant angle strain when forced to adopt a planar enolate geometry. The kinetic enolate is the more substituted (exocyclic) one because LDA plucks the most accessible proton.