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The Hydrolysis of Tert-Butyl Chloride Proceeds More Rapidly in a Solvent

Question 125

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The hydrolysis of tert-butyl chloride proceeds more rapidly in a solvent mixture which is 70% water/30% acetone than in one which is 30% water/70% acetone.Why?


A) The transition state in the carbocation formation step is better stabilized in the more polar solvent mixture.
B) The reaction proceeds by an SN2 mechanism wherein the rate is increased by increasing the concentration of the nucleophile water.
C) The reaction proceeds by an SN1 mechanism wherein the rate is increased by increasing the concentration of the nucleophile water.
D) The solvent which contains a greater percentage of water is less polar,and this destabilizes the tert-butyl chloride.
E) none of the above

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