Why is the alkyl halide shown below not capab | vedclass

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Question

(D) For an $E2$ reaction to occur,the leaving group $(Br^-)$ and the $\beta$-hydrogen must be in an anti-periplanar orientation ($180^\circ$ dihedral

Vedclass · Accepted Answer

The $C-H$ and $C-Br$ bonds which need to break cannot achieve an anti-periplanar orientation.

Vedclass · Answer

(D) For an $E2$ reaction to occur,the leaving group $(Br^-)$ and the $\beta$-hydrogen must be in an anti-periplanar orientation ($180^\circ$ dihedral angle).In the provided molecule,the bromine atom is in an axial position (if we consider the chair conformation). However,the adjacent $\beta$-hydrogens are not anti-periplanar to the bromine atom due to the specific stereochemistry of the methyl groups.Specifically,the $C-H$ bonds at the $\beta$-carbons are not oriented anti to the $C-Br$ bond,preventing the necessary orbital overlap for the concerted $E2$ mechanism.

Why is the alkyl halide shown below not capable of undergoing an $E2$ reaction upon treatment with sodium ethoxide?

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