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Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry

Arrange the following radicals in decreasing order of their relative stability: (I) CH ₃ CH = CH - C H ₂ (II) C H = CHCH ₃ (III) CH ₃ C HCH ₃

Options

  1. A(III) > (I) > (II)
  2. B(II) > (III) > (I)
  3. C(I) > (II) > (III)
  4. D(I) > (III) > (II)

Correct answer

D. (I) > (III) > (II)

Step-by-step solution

Radical (I) is an allylic radical, which is highly stabilized by resonance. Radical (III) is a secondary alkyl radical, which is stabilized by hyperconjugation from six -hydrogen atoms. Radical (II) is a vinylic radical, where the unpaired electron is present in an sp^2 hybridized orbital. It is highly unstable due to the higher electronegativity of the sp^2 carbon. Therefore, the decreasing order of stability is (I) > (III) > (II). Answer: (I) > (III) > (II)

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