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 intermediate carbocation and the stabilization of the transition state during its formation. In compound (iii), the chlorine atom is at the bridgehead position. Solvolysis would require the formation of a carbocation at the bridgehead carbon. According to Bredt's rule, a bridgehead carbocation in a small bicyclic system is highly unstable because it cannot achieve the required planar sp^2 geometry due to severe angle strain. Therefore, compound (iii) will have