100 80 60 20 d) C3H7NO2 IR Spectrum 1553 1387 (liquid film) سلا 4000 3000 2000 1600 1200 800 V (cm³) % of base peak 411 43 M+*=89 (<1%) Mass Spectrum C3H7NO2 40 80 120 160 m/e 200 240 280 13C NMR Spectrum (50.0 MHz, CDCI, solution) DEPT CH₂ CH, CH↑ proton decoupled solvent L L 200 160 120 80 40 0 8 (ppm) 1H NMR Spectrum (200 MHz, CDCI, solution) T expansion 4.0 3.0 2.0 1.0 ppm 10 9 8 7 6 5 4 3 2 1 TMS 0 $ (ppm)

4000 IR Spectrum quid film) 100 80 60 40 YI 2248 41 10 3000 43 40 proton decoupled "C NMR Spectrum (150 MHz CDC, solution) 68 DEPT CH, CH, 1 CHT 9 200 ¹H NMR Spectrum (600 MHz, CDC, solution) M83 (<1%) 80 120 2000 v (cm) 8 m/e 160 160 2.3 L 7 1600 2.2 200 ryper 1200 6 ▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬ 120 Mass Spectrum 240 21 2.0 expansions (not to scale) 800 I CsH₂N 280 5 expansion 80 4 270 255 256 255 expansion No significant UV absorption above 220 nm 27.0 245 250 255 1.0 3 40 L 2 0 8 (ppm) 1 1 TMS L 1 0 8 (ppm) 10 ¹H-¹C me-HSQC Spectrum (600 MHz, CDC, solution) Black cross-peaks CH and CH Red cross-peaks CH₂ ppm 20 ¹H-"C HMBC Spectrum (600 MHz, CDC), solution) -22 -24 -26 -28 116 118 120 122 124 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8 0.6 ppm ppm 20 22 -24 26 28 -116 118 -120 122 -124 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8 0.6 ppm IR: List bands and possible/probable structural units responsible Band (cm³) Possible…

IR Spectrum (liquid film) 184 4000 100 80 60 40 20 40 13C NMR Spectrum (50.0 MHz, CDCI, solution) proton decoupled 200 ¹H NMR Spectrum (600 MHz, CDCI, solution) 1 10 9 8 3000 % of base peak 80 128 my 2000 V (cm¹) 119 M+* 134 120 160 m/e expansion 124 ppm 160 1600 I 7 200 I 6 120 ppm 1200 800 Mass Spectrum C10 H14 280 solvent 80 240 I 5 7.4 1 4 expansion 3 Problem 95 UV Spectrum max 262 nm (log10 € 2.5) solvent: ethanol -CH3 C 40 7.2 2 1 0 8 (ppm) TMS 1 I 1 0 8 (ppm) 201

Myriam 1718 1. 4000 3000 1600 1200 800 V (cm¹) 100 Mass Spectrum 43 119 80 60 JIK M+* 40 176 20 161 C12 H16 O 40 80 200 280 120 160 m/e 13C NMR Spectrum (50.0 MHz, CDCI, solution) expansion 188 IR Spectrum (liquid film) % of base peak DEPT CH₂ CH₂ CH proton decoupled L 200 ¹H NMR Spectrum (200 MHz, CDCI, solution) J 1 9 10 I 8 2000 160 the 1 7 6 240 120 130 130 125 ppm 125 ppm L 5 expansion 1 80 1 4 solvent Problem 99 UV Spectrum max 262 nm (log₁0 € 2.5) solvent methanol 40 t I 3 1 2 4 08 (ppm) TMS 1 0 8 (ppm) 1 1 205