Past exam of the chemistry course of the year 1 of the natural sciences course of the University of Cambridge / 2022 / Paper 1 / 1 / c / ii / Solution

The $1621\mathrm{c}{\mathrm{m}}^{-1}$ absorption is predominantly the carbon–carbon double-bond stretching vibration of the electron-rich vinyl ether. resonance donation from an oxygen lone pair changes both its frequency and its electric dipole moment variation during stretching. There is no carbonyl in the assigned structure, consistent with the absence of a carbon-13 NMR signal in the usual ketone or acyl chloride region.