Fundamentals of Organic ChemistryChemistryAldehydes and Ketones
What is the major product obtained when cyclohexanone is treated with an aqueous Na ₂ CO ₃ solution?
Correct answer
2
Step-by-step solution
Cyclohexanone contains -hydrogens. When treated with a mild base like aqueous Na ₂ CO ₃ , it undergoes an aldol addition reaction. The base abstracts an -hydrogen from one molecule of cyclohexanone to form a nucleophilic enolate ion. This enolate ion then attacks the electrophilic carbonyl carbon of a second cyclohexanone molecule. Subsequent protonation from water yields a -hydroxy ketone. Specifically, the -carbon of the first cyclohexanone ring becomes bonded to the former carbonyl carbon of the second ring, whi