Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes
Identify the correct reactivity order for the E 2 elimination reaction of the following compounds with alcoholic KOH : (i) (ii) (iii)
Options
- A(iii) > (i) > (ii)
- B(i) > (iii) > (ii)
- C(i) > (ii) > (iii)
- D(ii) > (iii) > (i)
Correct answer
C. (i) > (ii) > (iii)
Step-by-step solution
The reactivity of alkyl halides towards E2 elimination with a strong base like alcoholic KOH depends primarily on the stability of the developing alkene character in the transition state. A more stable alkene product corresponds to a lower activation energy and a faster reaction rate. Compound (i), 1-chloro-1-phenylpropane, is a secondary alkyl halide. Elimination of HCl yields 1-phenylpropene. This is a disubstituted alkene that is highly stabilized by extended conjugation with the phenyl ring and hyperconjugation