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JEE Advanced levelSingle correct optionDifficulty 3 of 3o4089

When 2-bromobutane reacts with 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

  1. Awater converts the E2 mechanism into E1, which always gives substitution only
  2. Bwater drives the equilibrium to the left to give less ethoxide, and solvated hydroxide acts less as a base, so SN2 competes better
  3. Cwater is a polar aprotic solvent, which favours elimination less than SN2
  4. 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 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.
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