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Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes

Identify the correct order of reactivity of the following compounds towards E ₂ elimination with alcoholic KOH . (i) (ii) (iii)

Options

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

Correct answer

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

Step-by-step solution

For an E ₂ elimination to occur in cyclohexane derivatives, the leaving group ( Cl ) and the -hydrogen must be in an anti-periplanar geometry, which requires both to occupy axial positions in the chair conformation. Compound (i): cis-1-chloro-2-methylcyclohexane The substituents are cis ( Cl is down, Me is down). In the most stable chair conformation, the bulkier methyl group occupies the equatorial position (down), forcing the chlorine atom into the axial position (down). In this major conformation, the -hydrogen

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