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  4. Which carbocation is most stable?

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Q. Which carbocation is most stable?

JIPMERJIPMER 2005Organic Chemistry – Some Basic Principles and Techniques

Solution:

A phenyl group, in which there is a flow of electron due to resonance of the benzene ring, generally causes $-I$ effect, but truely speaking it can act as both electron donating as well as electron withdrawing groups, depending upon the nature of group with which it is attached. In $C _{6} H _{5} CH _{2}^{+}$, phenyl group is attached to electron deficient group, hence it will donate electron due to resonance in benzene ring and thus stabilise the cation.