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

Correct answer

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

Step-by-step solution

The stability of a carbocation is determined by the electron-donating or electron-withdrawing nature of the substituents attached to the benzene ring. All the given structures are para-substituted benzyl cations. The substituents are -OCH₃ , -OH , -NH₂ , and -Cl . The -NH₂ group in (iii) has a very strong +M effect because nitrogen is less electronegative than oxygen, making its lone pair more available for delocalization. This provides the maximum stability to the carbocation. Both -OH in (ii) and -OCH₃ in (i) gro

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