An $E2$$\mathrm{E2}$ (or $E1cb$$\mathrm{E1cb}$) mechanism requires antiperiplanar configuration. In case of restricted rotations, like in cycles, where rotation is not possible to achieve the antiperiplanar configuration, elimination occurs to favour the Hofmann product instead of the Zaitsev, if antiperiplanar configuration is possible at the less substituted β C. In menthyl chloride,
In menthyl chloride, antiperiplanar configuration is only seen with the red $\ce{H}$, so 2 menthene is the only product, although it is not the most substituted. In
againIn the molecule above, due to restricted rotation, the leaving group $\ce{Cl}$ and the base attacking the $\ce{H}$ will be on the same side. So will elimination be possible in this case?