necessary Chemistry Alkene and Alkyne enhancement Reactions Carbocation & Markovnikov's preeminence

Resonance Stabilization

Neighboring double bonds are far better stabilizers, due to the fact that they deserve to donate electron by resonance.

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Hence, the triphenylmethyl cation, #("C"_6"H"_5)_3"C"^"+"# is stable due to the fact that it has many resonance structures.

However, the resonance overlap of the π orbitals is no perfect because steric hindrance forces the ion to have a propeller shape.

(Adapted native


More stable is the tricyclopropylmethyl cation.


The bent bonds the the cyclopropane ring can overlap v the empty #"p"# orbital there is no steric hindrance.

(Adapted indigenous Wikipedia)

Arenium ions

Nothing beats the security of fragrant cations favor cyclopropenium and also cycloheptatrienylium (tropylium) cations.

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(Adapted from

The many stable carbocation

Add the conjugation through cyclopropyl rings, and also the many stable carbocation all set to date is most likely the tricyclopropylcyclopropenium cation.


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