Identify the correct decreasing order of the rate of solvolysis for the following compounds: (i) (ii) (iii)

Step-by-step solution

The rate of solvolysis depends on the stability of the carbocation intermediate and the presence of neighboring group participation (anchimeric assistance). In compound (ii), the cyclopropane ring is anti to the leaving tosylate (-OTs) group. The -electrons of the cyclopropane ring are perfectly aligned to provide strong anchimeric assistance via backside attack as the -OTs group departs. This leads to the formation of a highly stabilized non-classical carbocation, making the rate of solvolysis exceptionally fast.