Tuesday, July 23, 2019

organic chemistry - Stabilisation of carbocations through hyperconjugation


Our teachers told us that greater the number of alpha H, greater is the stability of carbocation.


But consider this:


$\ce{CH3CH2+}$ and. $\ce{CH3CH2CH2+}$


The first one has 3 alpha H while the second one has 2. So first one is more stable, as our teachers say. But even C-C sigma bond can participate in hyperconjugation, isn't it?


Going with that, second one has equal no bond resonating structures and even higher inductive effect of ethyl group. So second one should be more stable (without overruling the dominance of hyperconjugation).




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