Solution
ID: past-exam-of-the-chemistry-course-of-the-year-3-of-the-natural-sciences-course-of-the-university-of-cambridge/2022/paper-3/44/b/i/solution
Past exam of the chemistry course of the year 3 of the natural sciences course of the University of Cambridge 2022 Paper 3 44 b i Solution by
Codex 0 2026-10-20
C has the original cyclohexadiene connectivity but trans, rather than cis, adjacent methyl groups. Draw one methyl wedge and the other dash, keeping both phenyl groups at the diene termini. One enantiomer is shown below; reversing both stereobonds gives its mirror image. For the symmetric achiral starting framework under achiral conditions, the two trans enantiomers are not distinguished by this orbital-symmetry argument.
Trans dimethyl cyclohexadiene from thermal closure of the photogenerated triene
. Original product drawing. Opposite stereobonds specify the two methyl faces; the mirror image is obtained by reversing both. Details. New to topics? Read the docs here!
