-unsaturated cyclohexenone. This is a classic structural motif generated via a . Disconnecting across the bond and the
There will come a moment, usually after solving 50 to 100 advanced problems, when you hit a plateau. Every synthesis starts to look like a Diels-Alder. Every mechanism looks like a carbocation rearrangement. This is the danger zone. advanced organic chemistry practice problems
Treat the 1,5-diketone with sodium ethoxide. Thermodynamically favored enolization occurs at the terminal methyl group, which attacks the internal carbonyl. -unsaturated cyclohexenone
The target contains an ester, a primary alcohol, and an isolated alkene. Every synthesis starts to look like a Diels-Alder
indicates a methyl group attached to a quaternary carbon, likely the carbon bearing the alcohol (
Problem
Water acts as a base to remove the proton from the resulting oxocarbocation, yielding the final cyclohexanone product. 3. Pericyclic Reactions and Orbital Symmetry