The standard free energy of activation (DG ) for hydration of 2-methylpropene to

Chapter 4, Problem 4.70

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The standard free energy of activation (DG ) for hydration of 2-methylpropene to 2-methyl-2-propanol (Eq. 4.41, p. 173) is 91.3 kJ mol1 (21.8 kcal mol1 ). The standard free energy DG for hydration of 2-methylpropene is 25.56 kJ mol1 (21.33 kcal mol1 ). The rate of hydration of methylenecyclobutane to give an alcohol (compound X in 4.59) is 0.6 times the rate of hydration of 2-methylpropene. The equilibrium constant for the hydration of methylenecyclo butane is about 250 times greater (in favor of hydration) than the equilibrium constant for the hydration of 2-methylpro pene. Which alcohol, X or 2-methyl-2-propanol, undergoes dehydration faster, and how much faster? Explain.

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