Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes
Identify the correct order of reactivity of the following compounds towards the S_N1 reaction: (i) (ii) (iii)
Options
- A(i) > (iii) > (ii)
- B(iii) > (i) > (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 the S_N1 reaction depends directly on the stability of the carbocation intermediate formed after the departure of the leaving group (halide ion). Let us analyze the carbocations formed from the given compounds: 1. Compound (i) is cyclopropylmethyl chloride. Upon losing the chloride ion, it forms the cyclopropylmethyl carbocation. This carbocation is exceptionally stable due to the delocalization of the positive charge with the -electrons of the adjacent cyclopropane ring (oft