Which base would always be appropriate to deprotonate the carbon that is ? to a carbonyl carbonyl? lithium diisopropylamide sodium amide sodium ethoxide n-butyl lithium Solution Since, the hydrogen on the ? carbon is weakly acidic, so it reaquires strong base like lithium Diisopropylamide(LDA) to form stable enolate ion. Ie CH3(C=O)CH3 + LDA - - - > - CH2(C=O)CH3 (enolate ion) And this enolate form is resonance stabilzed. - ?CH2(C=O) CH3(enolate ) <-----> CH2=C(OH) CH3(enol) Note : this reaction can also be possible with sodium ethoxide also but being a weak base the deprotonatelion take place only to extent 0.1%. .