Let be the internal vinylic proton, the terminal proton trans to , the terminal proton cis to , the oxygen-bound methylene and the chlorine-bound methylene. The assignments areFor the doublet of doublets, pairing corresponding lines gives Hz and Hz. The larger value identifies trans vinylic coupling; the smaller identifies cis vinylic coupling. The resonance confirms the large splitting, approximately Hz, and has a small geminal coupling to .
The small spacings are not perfectly reciprocal if treated as exact First-order NMR multiplets: the lines imply Hz, whereas the lines imply Hz and Hz. Thus report Hz, Hz and – Hz, rather than asserting incompatible exact constants. Printed precision and departures from a simple first-order pattern limit this line-picking estimate; a full spin-system fit would be needed for refined values. Splittings alone do not establish the signs of these couplings.
The two methylene groups split one another into approximate NMR triplets, with Hz; the oxygen-bound triplet gives approximately the same value from its rounded line labels. The three vinylic protons plus two methylenes give the required seven-proton integral. The terminal vinylic protons are diastereotopic, because replacing one or the other creates different alkene geometries.
