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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3g2160

Which statements about alcohol acidity are correct?

  1. AIn the gas phase, tert-butyl alcohol is more acidic than methanol because the larger alkyl groups stabilise the alkoxide by polarisation.
  2. BIn water, methanol is more acidic than tert-butyl alcohol because the bulky alkoxide is less well solvated.
  3. CThe reversal of order between gas phase and water arises because the effect of alkyl groups disappears in water.
  4. DIn the gas phase, water is more acidic than methanol.

Answer: A, B

A and B are true: polarisability dominates in the gas phase and solvation of the small alkoxide dominates in water. C is false: the inductive effect does not vanish, solvation simply becomes the deciding factor. D is false: in the gas phase water is the least acidic of the series, the order being tert-butyl isopropyl ethyl methyl water.
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