Symmetrical molecule NMR challenge

Structure elucidation of symmetrical molecules can often be accomplished using NMR with few such examples given in Fig. 1.
While symmetry dramatically simplifies the ¹H-NMR spectra of many molecules, it also introduces features that might not be trivial to inexperienced spectroscopists. As an example, ¹H-NMR spectra of both E and Z isomers of symmetrical alkenes (Fig. 1) display a single signal corresponding to both sp² protons; however, its coupling pattern depends only on the substituent group R, and not on the coupling between the sp² protons. In addition, one cannot employ NOESY experiments to distinguish between the E and Z isomers because both sp² protons are chemically equivalent. Hence, one must resort to other approaches to interpret the NMR data.