Abstract
Abstract The solvolysis of 2,2-dimethyl-1-(p-methoxyphenyl)propyl p-nitrobenzoate in phenol provides a novel example of the common ion salt effect (rate depression) which arises at the stage of the second ion pair intermediate (Int-2; the rear-side shielded ion pair intermediate), not the dissociated (free) carbocation intermediate as generally supposed so far. This example demonstrates that “the common ion rate depression” could not give evidence for the intermediacy of the dissociated carbocation intermediate in the SN1 solvolysis, but an indicator for the stability of solvolysis intermediates including the ion pair intermediate.
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