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
- Ai > iii > ii
- Bii > iii > i
- Ci > ii > iii
- Diii > ii > i
Correct answer
D. iii > ii > i
Step-by-step solution
The given compounds undergo E 2 elimination with alcoholic KOH to form a double bond at the bridgehead position. According to Bredt's rule, the formation of a double bond at a bridgehead carbon is highly restricted in small bicyclic systems due to severe angle strain. The stability of a bridgehead alkene increases as the size of the rings in the bicyclic system increases. Larger rings provide greater flexibility, which better accommodates the planar geometry of the double bond and reduces the overall strain. The gi