Question

ORGANIC CHEMISTRY - H-NMR & C-NMR QUESTION

Propose a structure consistent with a compound with the molecular formula C8H14O by using the H-NMR, C-NMR and DEPT spectra provided (see image). Please note that in the H-NMR, the signal located at the chemical shift of 3.65 ppm disappears when 1 drop of D2O is added. And the triplet at 3.70 ppm and the 3 upfield signals have J = 7.0 Hz. The smallest coupling constant for the middle multiplets between 2.5 to 2.0 ppm is J = 1.5 Hz.

Please quickly explain (in point form) some of the logic used to obtain the structure.

Thanks =)

'H NMR and "C NMR/DEPT spectra of CsHisO: PPM CsHisO DEPT 90 only) CDO 82 80 78 ppm 8S 80 75 70 65 60 55 50 40 35 30 25 20 15 10 ppm proton decoupled 13C NMR