In a carbocation rearrangement, if the migrating tendency and the stability of the resultant carbocation directly oppose each other, which factor generally dictates the major product if the resulting

Question

In a carbocation rearrangement, if the migrating tendency and the stability of the resultant carbocation directly oppose each other, which factor generally dictates the major product if the resulting carbocation is highly stabilized by the resonance of a lone pair?

Prashant Kotian · Accepted Answer

Correct answer: C. According to advanced mechanistic principles, if both potential shifting pathways result in carbocations that are highly stabilized (e.g., by back-bonding from an oxygen or nitrogen lone pair, such as in the Pinacol rearrangement), the subtle difference in thermodynamic stability matters less. In such cases, the reaction is kinetically controlled, and the major product is determined by the inherent migratory aptitude of the groups.

💡 Solution & Explanation

Practice 22,000+ questions like this