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Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes

Identify the correct reactivity order for the E ₂ elimination reaction with alcoholic KOH for the following compounds: (i) (ii) (iii)

Options

  1. Aii > i > iii
  2. Bi > ii > iii
  3. Ci > iii > ii
  4. Diii > i > ii

Correct answer

A. ii > i > iii

Step-by-step solution

The rate of an E₂ elimination reaction is heavily influenced by the stability of the alkene product formed, as the transition state has partial double-bond character. A more stable product lowers the activation energy, leading to a faster reaction. Let us analyze the product formed by the elimination of HCl for each compound: For compound (i), the elimination of HCl yields cyclooctatetraene. Cyclooctatetraene is a non-aromatic compound because it adopts a non-planar, tub-like conformation to avoid anti-aromatic des

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