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
- A(i) > (iii) > (ii)
- B(iii) > (i) > (ii)
- C(ii) > (iii) > (i)
- 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