Acid-Base Reaction to Form Enolate Very strong base is required for complete reaction. CH3 CH3 HC HC H3CN-H n-BuLi Lithium HC-CH3 HC ~CH3 diisopropylamide O Li" LDA (-C3H)2N-H pK=19 pK2=40 Chapter 22 Chapter 22 10 Acid-Base Reaction to Form Enolate Very strong base is required for complete reaction. Lithium diisopropylamide N H HC CH3 H3C HC CH3 H3C n-BuLi N HC CH3 H3C HC CH3 H3C Li + _ O H H O - Li + H LDA + C3H7 ) (i- 2N H pKa = 19 pKa = 40 =>