I have a difficult question in my problem sheet that I cannot solve. I have been asked to explain the following observation:
I have a number of issues with this:
1) The fast reaction must be a syn-elimination. How can syn E2 elimination occur? If an E2 elimination is stereospecific because it must go through an anti-periplanar transition state surely syn-peri-planar elimination cannot happen.
2) How does the slow reaction even happen? The H and the Cl are never going to be in the same plane (syn or anti).
As a side question: does the boat conformation (which the bicyclic molecule must adopt) have equatorial and axial sites like the chair conformation does?