Home > Community > Is the SN1 reaction faster with an axial or equatorial leaving group?
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+ Cyclohexane
+ Chemistry
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Jumana Hasina

Is the SN1 reaction faster with an axial or equatorial leaving group?

Chris James  Follow

Conformations

In compund 2, both substituents can be placed in equatorial positions, whereas in 1 the $\ce{Cl}$ group is forced into an axial position since the bulky t-butyl group has to be placed equatorial. This makes compound 1 more unstable (higher energy), leading to a faster rate of formation of the carbocation.

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Entrepreneurial Mindset  Follow
Just to add: an alternative way of looking at it is that, with compound More
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Hong Zhuang  Follow
I think its highly unlikely that the cyclohexane will adopt a non-chair conformation. The chlorine will just be stuck in an axial position.More
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Jason Shearin  Follow
, upon leaving of the $\ce{Cl-}$, there is relief of 1,3-diaxial interactions. But it is really just a different way of describing the same thing.More
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