Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes
Identify the correct order of reactivity for the following compounds towards an S _ N 1 reaction: (i) (ii) (iii)
Options
- A(i) > (ii) > (iii)
- B(i) > (iii) > (ii)
- C(iii) > (i) > (ii)
- D(ii) > (iii) > (i)
Correct answer
B. (i) > (iii) > (ii)
Step-by-step solution
The reactivity of a compound towards an S _ N 1 reaction depends on the stability of the intermediate carbocation formed after the departure of the leaving group (chloride ion). In compound (i), the departure of the chloride ion forms a carbocation that is highly stabilized by the para-cyclopropyl group. The cyclopropyl ring adopts a bisected conformation, allowing for strong - conjugation (overlap of Walsh orbitals with the empty p-orbital of the carbocation). This provides exceptional stability, making it the mos