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11. The following molecule has a chemical formula of C3H15N30. Using a correlation table like the one on Page 574 of your textbook, cross out functional groups that are not present, circle functional groups that are present, and leave alone any functional groups that are uncertain. (6 pts) mm Key Peaks 3468 cm! 3067 cm 2990 cm 2825 cm 1693 cm 1639 cm 2000 1300 100 Figure 1: IR spectrum retrieved from SDBS database. Alcohol (C-0) Alkene (C=C) Amine (N-H) Aldehyde (C=0) Alkyne (C=C) Aromatic Ring (C=C) Alkane (C-H) Amide (C=0) Ketone (C=0) Alkene/Aromatic Ring (C-H)

12. The following molecule has a chemical formula of C4H₂O₂. Circle the only correct molecular structure to the provided NMR spectrum. (3 pts) Key Peaks 4.12 ppm (q, 2H) 2.04 ppm (s, 3H) 1.26 ppm (t, 3H) 11 10 9 8 7 6 2 1 0 HSP-03-534 Figure 2: NMR spectrum retrieved from SDBS database. OH 13. Use proper arrow pushing to show the two-step formation of the marked molecular fragment in the mass spectrum for acetone below. (4 pts) MS-IW-7880 SDBS NO. 319 acetone C3H60 (Mass of molecular ion: 58) 100 35 40 55 60 m/z Relative Intensity 80- 60- 40- 20- MS-14-7980 of 10 15 20 Source Temperature: 220 °C Sample Temperature: 150 °C Reservoir, 75 eV 25 30 5 ppm 4 45 3 50 H