Question

For the following questions, provide the following information. (1) Ifa molecular formula is provided, indicate the units of unsaturation in this molecule. (2) Label any important relevant peaks in the IR spectrum by indicating which type of bond it corresponds to (3) If the integration is not provided in the 'H NMR spectrum, determine the integration for each signal in th spectrum (4) Examine the mass spectrum carefully. If I have placed an asterisk above a peak, propose a valid structure this ion. (5) Label the 'H NMR and C NMR according to what type of Hor Cit corresponds to (6) Finally, propose a structure for the molecule corresponding to the spectra information provided for each these questions. Show all of your work for partial credit. The correct structural assignment is worth 1 to 1.5 pts, while (1) throu (5) is worth 1.5 to 2 points. Question number 10 is an unknown which I will give you. When I give you this sample, along with molecular formula, you will obtain an IR, a 'H NMR, and a '°C spectrum for this sample. With thu data, you will provide the following: 1. Units of unsaturation. (Show your work for partial credit.) 2. Label all relevant peaks in the IR. 3. Label all possible peaks in the 'H NMR spectrum. 4. Label all possible peaks in the '°C NMR spectrum. 5. Provide the identity of this compound. Feel free to use additional sheets of paper while working through this handout and turn these in in organized and legible form) to show your work for partial credit.

Answer 1

- 2 TMt 150 Moleular formula Cg Hooz 1. Unit of unsahurahon. U= 2C+2+ N -H-X - 18+2+0-10-0 - 5 10=5| Five degree of unschunction 12. IR Data u 1670 cmnl carbonyl frequency (Ketone conjugated) is 3000 Cmt c=c="H streaching frequency 3. 'H AMR Data a> 2.5d singlet 34 ie ~ CH₂ by 3.9 d singlet 34 ie O- CH3 c) 7.0 r doublet 2H je Aromatic proton. Td) 8.0 d doublet 2H ie Aromatic proton. 4. 13 CMR Data It shows seven sets of Carbon > 22 ppm., 54 ppm 112 , 130, 160 195, 132_

1 . All above date probable structure is 'H NMR ay CH3 + 2.5.5 singlet 17.0.8 doublets TH A 7.0 r doublet W 8.0 r doublett R 8.0 r doublet OCHZ 3.9 d singlet