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Compound A, C8H10O, has the IR and 1H NMR spectra shown. Propose a structure consistent with the observed spectra, and label each peak in the NMR spectrum. Note that the absorption at 5.5 d disappears when D2O is added.

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Amarildo KociajLv10
9 Jan 2021
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Related questions


(a) An optically inactive compound A (C6H10O4) can be resolved into enantiomers and has the following NMR spectra: 13C NMR: ? 13.5, ? 41.2, ? 177.9 1H NMR: ? 1.13 (6H, d, J = 7 Hz); ? 2.65 (2H, quintet, J = 7 Hz); ? 9.9 (2H, broad s, disappears after D2O shake) Draw either enantiomer, including wedge/dash bonds.(b) Give the structure for an isomer of compound A that has a melting point that is appreciably different from that of A yet NMR spectra that are almost identical to those of A. Include wedge/dash bonds.


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