NEST2026ChemistryGeneral Organic Chemistry
The compound that produces aromatic species upon deprotonation of the indicated hydrogen is:
Correct answer
1
Step-by-step solution
For a species to be aromatic, it must be cyclic, planar, completely conjugated, and contain (4n+2) electrons (Huckel's rule). Deprotonation involves the removal of H⁺ to form a carbanion. In compound (1), deprotonation forms a carbanion that can delocalize to form an enolate, but the ring contains an sp³ hybridized carbon, so it lacks complete conjugation. It is non-aromatic. In compound (2), deprotonation yields the 5-methylcyclopentadienyl anion. The ring is cyclic, planar, completely conjugated, and possesses 6