JEE Advanced levelOne or more correct optionsDifficulty 3 of 3g2130
Ethyl acetoacetate has pKa=10.7. For which bases is the conversion of ethyl acetoacetate into its enolate essentially complete (take logK≥4)? (pKa of conjugate acids: ethanol 15.9, water 15.7, HX2COX3 6.4, HCOX3X− 10.3.)
ANaOCX2HX5
BNaOH
CNaHCOX3
DNaX2COX3
Answer: A, B
logK: NaOEt=15.9−10.7=5.2; NaOH=15.7−10.7=5.0; NaHCOX3=6.4−10.7=−4.3; NaX2COX3 (carbonate, conjugate acid HCOX3X−) =10.3−10.7=−0.4. Only the first two exceed 4.