Friday 12 August 2016

organic chemistry - Is the t-butyl carbocation more stable than the benzyl carbocation?


Various authors have different views regarding stability order of the benzyl and t-butyl carbocations.


$$\ce{PhCH2+ ; (CH3)3C+}$$



In my opinion, resonance effect dominates, so the benzylic carbocation should be more stable. But in the other case, both the inductive and hyperconjugation effects are present, which stabilize the intermediate carbocation.


What should is the correct stability order? Especially when you consider them in SN1 reactions, and what their effect on their rate is.




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