Why is the alkyl halide below not capable of undergoing an E2 reaction upon treatment with sodium ethoxide? A)Br^- is too poor a leaving group. B)The substrate is too hindered. C)Too much angle strain would be present in the alkene product. D)Sodium ethoxide is a poor base to use in E2 reactions. E)The C-H and C-Br bonds which need to break cannot achieve an anti-periplanar orientation.

Question

Quizplus · Accepted Answer

In E2 reactions, the leaving group and the proton that is removed must be anti-periplanar to each other. In the given substrate, the C-H and C-Br bonds cannot achieve an anti-periplanar orientation due to steric hindrance caused by the bulky tert-butyl group. Therefore, the substrate is not capable of undergoing an E2 reaction upon treatment with sodium ethoxide.

Why Is the Alkyl Halide Below Not Capable of Undergoing