Is $\ce{CF_3+}$ more stable than $\ce{CH_3+}$?
In $\ce{CF_3+}$, there is $\ce{C-F}$ back bonding that increases stability of the carbocations. But -I effect of $\ce{F}$ dominates +R effect and this decreases the carbocation stability. How can I compare these two competing effects to find the more stable carbocation?
Also, is $\ce{CF_3+}$ more stable than $\ce{CH3-CH+-CH_3}$ and tert-butyl carbocation?
Answer
$\ce{CF3+}$ is more stable than $\ce{CH3+}$. The comparison between -I and +R effect is made while talking about activation or deactivation of halogens when substituted on benzene. Fluorine always stabilises a carbocation to a large extent because of a very good overlap of $\ce{2p -~2p}$ orbitals.
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