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Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry

Choose the correct order of stability for the following carbocations: (I) (II) (III) (IV)

Options

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

Correct answer

C. I > II > IV > III

Step-by-step solution

The stability of the given benzyl carbocations is determined by the electron-donating effects of the - CH ₃ and - CD ₃ groups. The - CH ₃ group has a stronger hyperconjugation ( + H ) effect than - CD ₃ because the C - H bond is weaker than the C - D bond. However, the - CD ₃ group has a stronger inductive ( + I ) effect than - CH ₃ . For para-substituted carbocations (I and II), both + H and + I effects operate. Since the + H effect dominates over the + I effect, the stronger + H of - CH ₃ makes (I) more stable th

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