The major product which results when 2-chloro-2-methylpentane is heated in ethanol is an ether. From which mechanistic pathway does this ether arise?

Question

Quizplus · Accepted Answer

The formation of an ether from 2-chloro-2-methylpentane in ethanol likely proceeds via an S_N1 mechanism. This is because the substrate is tertiary, favoring carbocation formation, and ethanol, a polar protic solvent, stabilizes the carbocation intermediate, allowing nucleophilic attack by ethanol to form the ether.

The Major Product Which Results When 2-Chloro-2-Methylpentane Is Heated in Ethanol