The major product from the reaction of 2-chloro-2-methylpentane with sodium ethoxide in ethanol results from which of the following mechanistic pathways?

Question

Quizplus · Accepted Answer

The reaction of 2-chloro-2-methylpentane with sodium ethoxide in ethanol proceeds through an E2 mechanism. This is evidenced by the fact that elimination of the leaving group (chloride ion) and the proton on the adjacent carbon (beta-elimination) occur simultaneously. The relatively strong base (sodium ethoxide) and the absence of a hindered base suggest that the reaction is not likely to proceed through an E1 mechanism. Additionally, the absence of an SN1 resonance-stabilized carbocation intermediate militates against the SN1/U1 reaction pathways. Finally, the presence of a relatively strong nucleophile (ethoxide ion) and the need for a concerted mechanism argues against the Ecb pathway.

The Major Product from the Reaction of 2-Chloro-2-Methylpentane with Sodium