[mohit.shurtugal]

My teacher says that phenyl carbocation will not show resonance...why is that so?

i thought of hybridization and that maybe the sp carbon wouldn't survive in the ring

[NahiEw]

There are no electrons that can accommodate for the positive charge on the carbon. If you think the double bond could donate its electrons to the positive charge, then think about what happens to aromaticity (it would be lost essentially).

Also, the hybridization for that carbon is not sp, it's sp2 still. It's just that one of the sp2 orbitals is empty (or you can say the positive charge is there).

[mohit.shurtugal]

Am still confused.
I came across this in the "Haloarenes" chapter
While speaking of the factors which affect the chemical reactions of halo arenes, they mention the instability of the phenylic carbocation.
to quote-"in halo arenes the phenyl carbocation formed as a result of self ionization is not stabilized by resonance"

in chlorobenzene the carbons are sp2 hybridized. thden on losing the halide as cl- how does it remain sp2? and why is resonance hindered