Which of the following substrates will undergo maximum racemization upon solvolysis under identical conditions?

Step-by-step solution

Solvolysis reactions proceed via an S_ N 1 mechanism, which involves the formation of a carbocation intermediate. The extent of racemization in an S_ N 1 reaction is directly proportional to the stability of the intermediate carbocation. A highly stable carbocation has a longer lifetime, allowing the leaving group to diffuse away completely. The resulting free, planar carbocation can be attacked by a nucleophile from either face with equal probability, leading to maximum racemization. Evaluating the stability of th