Wednesday, July 10, 2019

organic chemistry - Which of the following is the more stable carbocation?


Which of the following is the more stable carbocation?


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I thought the 1st carbocation would be the more stable one as the pi-electron density of phenyl group can overlap with the vacant orbital on the sp-hybrid carbocation (1st one). But my tutor pointed out that the vacant orbital on carbon can never be parallel to the p-orbitals of the phenyl group carbons and overlap cannot occur. So only negative inductive effect of phenyl group has to be considered, and so the 2nd one will be more stable.


Please explain. Please also mention about some sources where I can read about these type of carbocations.




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