Why Are Vinylic Carbocations Unstable

Finally vinylic carbocations in which the positive charge resides on a double bonded carbon are very unstable and thus unlikely to form as intermediates in any reaction. Hence the vinylic cation is less stable than a typical alkyl cation. In fact in these carbocation species the heteroatoms actually destabilize the positive charge because they are electron withdrawing by induction.

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