4) The hydrolysisof tert-butyl chloride proceeds more rapidly in a solventmixtur

Question

4) The hydrolysisof tert-butylchloride proceeds more rapidly in a solventmixture which is 70% water/30%

acetone than in one which is 30% water/70%acetone. Why?

A) The solvent which contains a greaterpercentage of water is less polar, and this destabilizesthe tert-butyl

chloride.

B) The reaction proceeds by an SN2 mechanismwherein the rate is increased by increasing theconcentration

of the nucleophile water.

C) The transition state in the carbocationformation step is better stabilized in the more polar solventmixture.

0) The reaction proceeds by an SNI mechanism wherein the rate isincreased by increasing the concentration

of the nucleophilewater.

E) none of theabove

Explanation / Answer

3y halides undergo Sn1 via asolvolysis, and is dependent only on [alkyl halide]. The key tothis reaction is stabilization of thecarbocation. C) The transition state in the carbocation formation step is betterstabilized in the more polar solvent mixture. (technically itshould say intermediate rather than transitionstate)

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