Which of the following alkyl halides would afford the indicated product upon reaction with sodium ethoxide?

Question

Quizplus · Accepted Answer

The given reaction is a Williamson ether synthesis, in which an alkyl halide reacts with a strong base to form an ether. This reaction proceeds through an S_N2 mechanism, and therefore requires a primary or methyl alkyl halide. Option A is a tertiary alkyl halide, so it will not undergo an S_N2 reaction. Option C is a secondary alkyl halide, which may undergo an S_N2 reaction, but the resulting ether will have a different structure than the one indicated in the question. Option D is also a secondary alkyl halide, and the indicated product cannot be formed from it. Option B, on the other hand, is a primary alkyl halide, and can undergo an S_N2 reaction with sodium ethoxide to form the desired ether.

Which of the Following Alkyl Halides Would Afford the Indicated