Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes
Identify the correct order of reactivity of the following compounds towards an E 2 elimination reaction using alcoholic KOH : (i) (ii) (iii)
Options
- A(i) > (ii) > (iii)
- B(iii) > (i) > (ii)
- C(ii) > (i) > (iii)
- D(i) > (iii) > (ii)
Correct answer
C. (ii) > (i) > (iii)
Step-by-step solution
For an E 2 elimination reaction to occur in a cyclohexane ring, the leaving group and the -hydrogen must be in an anti-periplanar arrangement, which means both must occupy axial positions. Let's analyze the given structures: The chlorine atom is located at C ₁ and is pointing 'down'. For it to be axial, the ring must adopt a chair conformation where the 'down' position at C ₁ is axial. The adjacent carbons are C ₂ and C ₆ . At C ₆ , there are two methyl groups and no -hydrogens, so elimination cannot occur towards