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Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry

Identify the correct order of relative stability for the following carbocations: (I) (II) (III)

Options

  1. AI > III > II
  2. BI > II > III
  3. CIII > II > I
  4. DII > III > I

Correct answer

C. III > II > I

Step-by-step solution

Carbocation (I) is a vinylic carbocation ( CH₂=C^+-CH₃ ). The positive charge is present on an sp -hybridized carbon atom. Since sp -hybridized carbons are more electronegative, they do not readily accommodate a positive charge, making this carbocation highly unstable. Carbocation (II) is a secondary alkyl carbocation (isopropyl cation, CH₃-CH^+-CH₃ ). It is stabilized by hyperconjugation from six -hydrogens and the +I effect of two methyl groups. Carbocation (III) is a secondary benzylic carbocation (1-phenylethyl

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