Identify the major product formed in the following reaction sequence.

Step-by-step solution

The reaction of fluorenone with diazomethane ( CH ₂ N ₂ ) results in a ring expansion. The methylene group inserts adjacent to the carbonyl group, expanding the central five-membered ring to a six-membered ring to form phenanthren-9(10H)-one. Phenanthren-9(10H)-one rapidly tautomerizes to its highly stable, fully aromatic enol form, 9-phenanthrol. Treatment with sodium hydride ( NaH ) deprotonates the hydroxyl group of 9-phenanthrol, forming a phenoxide anion. Subsequent reaction with methyl iodide ( MeI ) leads to