MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms IV: Elimination / E1cB mechanism
JEE Advanced levelSingle correct optionDifficulty 3 of 3o4147

For the base-induced loss of water from , the ease of E1cB elimination follows the acidity of the alpha C-H of (typical pKa values: ketone about 19, ester about 25, amide about 30, alkane about 50). The decreasing order of ease of elimination for (a) , (b) , (c) , (d) is

  1. Ab > a > c > d
  2. Ba > c > b > d
  3. Cd > c > b > a
  4. 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.
Practice Organic Reaction Mechanisms IV: Elimination More on E1cB mechanism

More questions on E1cB mechanism