IR Spectrum (quid film) 4000 100 8282& 80 60 40 20 % of base peak 3000 43 40 13C NMR Spectrum (500 MHz, CDCI, solution) 80 DEPT CH CH CH proton decoupled 200 ¹H NMR Spectrum 2000 V (cm'¹) M** 122/124 120 160 m/e 1600 160 1200 120 800 Mass Spectrum C3H,Br 280 solvent 80 200 240 Problem 15 No significant UV absorption above 220 nm 40 08 (ppm)

Problem 7 2249 IR Spectrum (KBr disc) 4000 3000 2000 1600 1200 800 v (cm') 100 Mass Spectrum 80 53 60 No significant UV 40 M+' = 80 absorption above 220 nm 40 20 C4HẠN2 160 m/e 40 80 120 200 240 280 T 13C NMR Spectrum (100.0 MHz, CDCI, solution) DEPT CHat CH, сн+ proton decoupled solvent 200 160 120 80 40 8 (ppm) H NMR Spectrum (400 MHz, CDCI, solution) TMS 10 1 8 (ppm) 9 7 6. 4 % of base peak 5

m 00 trum solutic 4000 88892 IR Spectrum (liquid fem) 100 80 60 40 20 % of base peak m 1600 v (cm¹) 68 M 147/149 40 80 120 160 m/e 13C NMR Spectrum (100 MHz. CDC, solution) 10 3000 54 DEPT CHY CH1 CHA proton decoupled 200 ¹H NMR Spectrum (200 MHz. CDCI, solution) 108 2249 2000 160 expansion 34 30 26 9 8 7 1200 800 Mass Spectrum C₂H6NBr 200 240 280 120 22 ppm 6 5 solvent 1 80 4 Problem 19 No significant UV absorption above 220 nm 40 3 0 125 8 (ppm) TMS 1 0 8 (ppm) 2 1

What is the IR and HNMRAndCNMR and mass

A student performed a series of reactions and obtained the spectral data provided. The reaction sequence is shown below.. What are the structures for A, B, C, and D? Compound B NMR (relative integrated areas below peaks) CH;CH,O°N 1. BHTHF N-bromosuccnimide A CH;CH,OH B 2. H,O,/OH- D hv reflux Compound A NMR (relative integrated areas below peaks) PPM 5 Compound B IR INFRARED SPECTRUM PPM 5 1 6 0.8 Compound A IR INFRARED SPECTRUM 0.6 0.8 0.4 0.4 0.2- 3000 2000 Wavenumber (cm-1) 1000 The MS of compound B shows an M+ peak at 198 and an M+2 peak at 200 with a relative abundance of 1:0.97 2000 Wavenumber (cm-1) 3000 1000 Transmitance Relative Transmittance

Identify the peaks and structure.

опанит 1715 1600 IR Spectrum 100 4000 (liquid film) 43 80 75 60 M 40 20 % of base peak 10 3000 40 C 13C NMR Spectrum (20.0 MHz, CDCI solution) proton decoupled 9 80 200 ¹H NMR Spectrum (100 MHz, CDCI, solution) 101 8 2000 v (cm¹) M** 132 120 160 m/e 160 7 6 1200 120 Mass Spectrum 200 240 280 800 C-H 5 C6H1203 solvent L 80 4 -CH3 No significant UV absorption above 220 nm 3 H-C-H u -CH3 40 2 59 TMS 0 1 8 (ppm) TMS 0 8 (ppm)

100 80 60 20 % of base peak 30 40 80 V (cm¹) M**#103 120 160 m/e 200 Mass Spectrum C4H9NO₂ 240 280 21 No significa absorption ab

13C NMR is less sensitive than 'H NMR because of the greater mass of carbon. True False

Unknowns for 1H NMR Final Report 10) Chemical Formula: C₁₂H1s (hard to see but, all peaks that integrate to 1H are doublet of doublets) IR: peak at 1650cm-1 2H 10 2H 1H u 7 1H 11) Chemical Formula: C₁0H12O2 IR: strong peak 1720cm-¹ 6 1H 1H 1H 8 12) Chemical Formula: C₂H₂00 IR: strong broad 3300cm-1 5 2H 2H 1H 3 4 PPM 6 PPM -3 septet 1H PPM 9H 6H 18H 0