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Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry

Arrange the following carbocations in decreasing order of their stability: (i) (ii) (iii) (iv)

Options

  1. A(i) > (ii) > (iv) > (iii)
  2. B(iii) > (iv) > (i) > (ii)
  3. C(ii) > (iii) > (i) > (iv)
  4. D(iii) > (iv) > (ii) > (i)

Correct answer

D. (iii) > (iv) > (ii) > (i)

Step-by-step solution

The stability of carbocations is determined by the +I effect, hyperconjugation (number of -hydrogens), and the hybridization of the carbon bearing the positive charge. Carbocation (i) is a vinylic carbocation where the positive charge is present on an sp -hybridized carbon. Due to the high s -character ( 50 % ) and higher electronegativity of the sp carbon, it is highly unstable and the least stable among the given options. Carbocation (ii) is a primary ( 1^ ) carbocation (cyclohexylmethyl cation). It is stabilized

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