= Solution
The <vinyl ether> has an important <resonance contributor>
$$
\mathrm{CH_2=CH-O-R\ \leftrightarrow\ {}^-CH_2-CH=O^+-R},\qquad R=\mathrm{CH_2CH_2Cl}.
$$
Donation from <oxygen> into the <conjugated system> increases <electron> density at the terminal unsaturated <carbon>, helping explain its unusually shielded $\delta_C=87.4$ ppm and its terminal <protons> near 4.1–4.2 ppm. The directly oxygen-bound unsaturated <carbon> is strongly deshielded at $151.1$ ppm; its <proton> at $6.480$ ppm also experiences the <oxygen> substituent and <alkene> magnetic anisotropy. These trends are consistent with the whole delocalized electronic structure; a <chemical shift> is not simply a meter for an atom's <partial atomic charge>.
For the saturated part, the stronger local deshielding by <oxygen> places $\mathrm{OCH_2}$ at $\delta_C=67.8$, $\delta_H\simeq3.948$, while $\mathrm{CH_2Cl}$ lies at $41.9$ and $3.708$ ppm. The two terminal vinylic <protons> have different geometrical relationships to the <oxygen> substituent and therefore different <chemical shifts> as well as different <vicinal couplings>.
Back to article page