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 via the S_N1 mechanism depends on the stability of the intermediate carbocation formed after the departure of the leaving group (tosylate, OTs). 1. Compound (ii) forms a bridgehead carbocation in a bicyclo[3.3.1]nonane system. Because the rings are relatively large (two fused six-membered rings), the system is flexible enough to allow the bridgehead carbon to achieve a nearly planar sp^2 geometry. This makes the bicyclo[3.3.1]non-1-yl carbocation the most stable among the three, leading to th