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Question

The stability order of the following carbocations is :

A
(i)>(ii)>(iii)
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B
(iii)>(i)>(ii)
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C
(ii)>(i)>(iii)
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D
(i)>(iii)>(ii)
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Solution

The correct option is C (ii)>(i)>(iii)
In structure (i):
There is no resonance taking place, it is only stabilized by hyperconjugation due to presence of α-hydrogens.
In structure (ii) :
Even though it has less α-hydrogens than structure (i), this structure is stabilized by resonance. So, it is more stable than structure (ii) because resonance effect is more dominating than hyperconjugation.
In structure (iii) :
This structure is planar, is cyclic, has conjugation and has 4 π e thus making it anti aromatic. Since anti-aromatic structures are the least stable. So, correct order of stability is : (ii)>(i)>(iii)

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