The benzene C−H bonds are sp2 hybridized. Because the electrons are closer to the nucleus with a high s character, we must use more energy to remove them and break the bond. Because of the high bond energy of the aromatic C−H bond, the phenyl carbocation is unstable. ...

Does phenyl stabilize carbocation?

The effect of this resonance is to make the carbocation more stable when the charge and the electron deficiency are located on a carbon which is directly bonded to the phenyl group. Such a carbon is called a "benzylic" carbon. ... We've seen that benzylic carbocations are stabilized by resonance.

Why benzyl cation is more stable than phenyl cation?

Benzyl carbocation is more stable as the +ve charge on the ch2 group is resonance stabilised with the benzene ring. In phenyl carbocation, the +ve charge occurs in the ring itself and is therefore not resonance stabilized.