JEE Advanced levelSingle correct optionDifficulty 3 of 3o4089
When 2-bromobutane reacts with KOH in dry ethanol, the major product is but-2-ene. If the ethanol is progressively replaced by water, the proportion of butan-2-ol rises. The best explanation is
Awater converts the E2 mechanism into E1, which always gives substitution only
Bwater drives the equilibrium EtOX−+HX2OEtOH+OHX− to the left to give less ethoxide, and solvated hydroxide acts less as a base, so SN2 competes better
Cwater is a polar aprotic solvent, which favours elimination less than SN2
Dwater increases the steric hindrance at the alpha carbon of 2-bromobutane
Answer: B
In alcoholic KOH some ethoxide is present, and it is a stronger base than hydroxide. Adding water shifts EtOX−+HX2OEtOH+OHX− toward hydroxide, which is further tamed by strong hydrogen-bonding solvation. A weaker, more solvated base reduces E2 relative to SN2, so the alcohol proportion increases.