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Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry

Determine the correct decreasing order of the relative rate of reaction for the following compounds with aqueous EtOH / AgNO ₃ . (I) (II) (III)

Options

  1. AIII > II > I
  2. BI > II > III
  3. CIII > I > II
  4. DI > III > II

Correct answer

A. III > II > I

Step-by-step solution

The reaction of halides with aqueous EtOH / AgNO ₃ proceeds via an S _ N 1 mechanism, where the rate-determining step is the formation of a carbocation. The rate of reaction depends on the stability of the carbocation and the leaving group ability. Compound (I) is a vinylic chloride. The cleavage of the C-Cl bond produces a vinylic carbocation, which is highly unstable. Hence, it is the least reactive. Compound (II) is an allylic chloride. It forms a secondary allylic carbocation, which is stabilized by resonance w

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