JEE Advanced levelSingle correct optionDifficulty 3 of 3o4147
For the base-induced loss of water from HOCHX2CHX2Y, the ease of E1cB elimination follows the acidity of the alpha C-H of CHX3Y (typical pKa values: ketone about 19, ester about 25, amide about 30, alkane about 50). The decreasing order of ease of elimination for Y= (a) COCHX3, (b) COOCX2HX5, (c) CONHX2, (d) CHX3 is
Ab > a > c > d
Ba > c > b > d
Cd > c > b > a
Da > b > c > d
Answer: D
The E1cB rate depends on how easily the beta carbon loses a proton to form the carbanion, so the order follows acidity of the C-H: ketone (pKa about 19) > ester (about 25) > amide (about 30) > alkyl (about 50). The order is a > b > c > d.