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- NMR data Summary NMR solvent: DMSO-d6 'H NMR: Splitting (Multiplicity) Integration Chemical Shift 9.67 singlet 1H singlet doublet 9.17 7.37 6.72 2.00 1H 2H doublet singlet 2H 3H 1"C NMR: Chemical Shift 167.8 153.3 131.1 121.1 115.1 23.8 15N NMR: Chemical Shift 132.3 Instructions: Step 0: Look at the structure of Tylenol. Determine integration, and splitting you are expecting in the 'H NMR. Step 1: Look at the integration and splitting of the signals in the H NMR spectrum - assign the chemical shift of the protons of the methyl group; make a note which signals in the 'H NMR are due aromatic protons, NH and/or OH. Step 2: Look at the 'HSN HSQC spectrum - Use this spectrum to assign the chemical shifts of the NH proton and the OH proton. Step 3: Look at the 'H1SN HMBC spectrum - Use this spectrum to assign the chemical shifts of the aromatic protons in the 'H NMR. Step 4: Look at the 13C NMR spectrum - Make a note which carbon atoms are aromatic and/or alkyl. Assign the chemical shift of…Interpret the NMR spectrum 11 1 10 51 9 8 00 4 7 6 5 ppm 4 C,H,O,N M. Wt = 139 3 N 1 0NMR data Summary NMR solvent: DMSO-d6 'H NMR: Splitting (Multiplicity) Chemical Shift Integration 9.67 9.17 7.37 6.72 2.00 singlet singlet doublet doublet singlet 1H 1H 2H 2H 3H 13C NMR: Chemical Shift 167.8 153.3 131.1 121.1 115.1 23.8 15N NMR: Chemical Shift 132.3 Using the NMR spectra and the chemical shifts values from the previous page, assign the chemical shifts of the hydrogen atoms by writing the 'H NMR chemical shifts values into the boxes. н H но -CH3 -N. H, >H-O - H H Using the NMR spectra and the chemical shifts values from the previous page, assign the chemical shifts of the carbon atoms by writing the 13C NMR chemical shifts values into the boxes. CH3 -N. H. H-O4
- Analyze the H-NMR and C-NMR data below 10 9 8 7 H-NMR 6 200 180 160 140 120 C-NMR ppm 100 80 ppm 3 2 60 40 20 0 Assign. AQU C Shift (ppm) 7.804 7.607 2.577 Ppm Int. 196.90 199 135.86 274 131.89 1000 129.83 995 128.28 284 26.50 363A 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 TransmittanceIdentify the structure of the molecule most consistent with the molecular formula CgH8O₂ with 13C NMR delta peak values at 41.8, 123.7, 129.2, 132.3, 139.6, 141.5, 144.7, and 190.8. ol ol A. B. HO C. D. of OH
- 1. Given the IR and MS spectra, identify the following unknown with molecular formula (C5H10). 0.9 0.75 0.6 0.45 3089 2975 3000. 1648 2000. WAVENUMBER (cm-1) 885 1000. 100.- 80. 60.- 40.- 20. 0. 0. 15 15. d. Propose a structure consistent with this information. 29 c. To what do MS fragments at m/z = 70, 55, and 29 correspond? 30. m/z a. Calculate the hydrogen deficiency index for the molecule (show your work). 45. b. To what do the IR absorptions at 3089, 2975, 1648, and 885 cm³¹ correspond? 60. 70 75.From the spectra, determine the structure of the molecule.Remember to ignore the triad in the 13 C NMR spectrum at 77 ppm thatcomes from the NMR solventAnalyze this NMR and determine the unknown compound. Molecular weight= 120.15 Element Composition %C-79.97 %H-6.71 %O-13.32
- 7.) From the following sets of data, please propose a reasonable structure for the unknown organic compound. This molecule is entirely composed of C, H, and N only. Please show all of your work and feel free to write on the spectra any clues as to the structure. 4000 3000 2000 1000 S DO Infrared spectrum of unknown. KBr salt plate sample. 100 MS-NU-6396 80 60 40 20 - 10 20 30 40 50 60 70 80 90 100 110 m/z Mass spectrum of unknown. Molecular ion = 83.1 Relative IntensityA compound has the molecular formula: C4H8O2 and gives the following H-1 NMR spectrum. Give the functional groups responsible for the signals, which integrate as 2H, 3H and 3H (downfield to upfield). nmrsim presentation 1 1 C: Bruker TopSpin3.5p17\examdata elle 3.0000 SODEŹ quartet is CH₂, singlet is CH3 and triplet is OCH3. quartet is CH3, singlet is OCH₂ and triplet is OCH3 quartet is CH₂, singlet is OCH3 and triplet is CH3. quartet is OCH₂, singlet is CH3 and triplet is CH3. quartet is OCH₂, singlet is CH₂ and triplet is CH3. POSE (ppm) 10 [rel]Question 5 Analyse the 'H NMR spectrum of benzocaine below and complete the table of 'H NMR spectroscopic data. (Redraw the table in your answer book and complete) Atom # SH Integration Multiplicity 1 2 3 4 5 6 7 8 9 10 11 12 Sy 18.5 10.0 9.5 9.0 8.5 (2) 8.0 CHCI 7.5 7.0 Benzocaine/CDC13 (4) (2) 6.5 6.0 $.5 5.0 4.5 pom 4.0 3.5 3.0 2.5 H₂O 2.0 (3) 1.5 1.0 0.5 TMS 0.0 -0.5