Fundamentals of Organic ChemistryChemistryAldehydes and Ketones
Identify the major product formed in the following reaction:
Correct answer
3
Step-by-step solution
Cyclopentadiene has highly acidic methylene protons because the removal of a proton yields the cyclopentadienyl anion, which is aromatic ( 6 electrons). The base, sodium ethoxide ( C ₂ H ₅ ONa ), abstracts a proton from cyclopentadiene to form the cyclopentadienyl anion. This nucleophilic anion attacks the electrophilic carbonyl carbon of acetone ( CH ₃ COCH ₃ ) in a nucleophilic addition reaction, forming an alkoxide intermediate. Protonation by ethanol yields the corresponding alcohol. Since the reaction mixture