Question

3. (10 pts) Propofol is a drug that is used for the induction of anesthesia. It is the drug that ultimately killed the singer Michael Jackson. It has the chemical formula of C12H180. It turns out that Propofol and one of its structural isomers have 13C NMR spectra that show only 6 absorbances, with two below 358 and four between 100 and 1508. Both isomers show a strong absorbance in the IR (thin film/DCM) centered around 3450 cm '; the peak has slight broadening (not from the presence of water in the sample). One of the compounds more readily dissolves to give a positive Ferric Chloride test. The other, less soluble compound, needs to be dissolved in a quantity of DCM before it gives a + test. Based on this information, draw possible structures for Propofol and its isomer that are consistent with this spectral and qual analysis data and be sure to number one set (#1 thru 6) of the unique carbons in each structure.

Answer 1

SATURDAY 23 TODAY 12 Higo Double leond equivalent: - 12 - 18.+ 1 12-9+1 2 Structure has ring + double bond = 4 in number IR peak at 3450 cmt confirms about OH group 24 com bond gives positive feric cloride test, this means there is phenolic group. 3 ol OH + felly Peco Ph]z + 3 Ha (Greenpopt)

12 carbon atoms are 25 there but only 6 BC, peaks indicate simmetry in structure. So possible structures are CH3 TUESDAY OH Both structure have & - carbon atom. 8 types of