A student found an old bottle labeled "thymol" on the stockroom shelf. After noticing a pleasant odor, she obtained the following mass, IR, and NMR spectra. The NMR peak at d4.8 disappears on shaking with D2O. Propose a structure for thymol, and show how your structure is consistent with the spectra. Propose a fragmentation to explain the MS peak at m/z 135, and show why the resulting ion is relatively stable.
