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- When the 1HNMR spectrum of an alcohol is run in dimethylsulfoxide (DMSO) solvent rather than in chloroform, exchange of the Ο-H proton is slow and spin-spin splitting is seen between the Ο-H proton and C-H protons on the adjacent carbon. What spin multiplicities would you expect for the hydroxyl protons in the following alcohols? (a) 2-Methyl-2-propanol (b) Cyclohexanol (c) Ethanol (d) 2-Propanol (e) Cholesterol (f) 1-MethylcyclohexanolFor the following 9 compounds (most of which were the ones used in this lab), tell me what peaks you would expect to see in the 'H-NMR spectrum of those compounds. I have provided table for you to fill out with approximate chemical shift (ppm units), peak multiplicity_(singlet, doublet, etc.) and integration of the signal (how many protons would give that signal). No IR data is required. In addition, tell me the number of 13C-NMR signals you would expect to see [specific 13C shifts are not required] PredictThe compound whose IR spectrum is shown below has the following functional group: 4000 3500 2500 WAVENUMBER [cm-1] 3000 2000 1500 1000 500 primary amine O ester O ketone O alcohol O alkyne TRANSMITTANCE [%] 08 09
- 2. READ THE DIRECTIONS TO EACH QUESTION CAREFULLY - not following the directions means you get the question wrong! 3. FORMAT YOUR ANSWERS AS DIRECTED - formatting your answers incorrect means you get the question wrong! 4. Below are the IR regions and NMR chemical shifts table for use with the spectroscopy problems: 'H NMR 12 11 R 20 ΟΞΟ 10 OH R 0=C H 9 8 7 ppm 6 OH H C=C-H 5 NH H-C-X H-C-O -OH X = F, Cl, Br (i.e. electronegative atom) 3 -NH 2 H-C-N H-C-S HC- 1 -CH3 -CH₂- CEC-H H-C-C=O -CH H-C-C=C 0 4000 DID small range range of values broad peak =C-H ⇓ 3250- 3300 N-H broad with spikes -3300 -O-H broad-3300 -3400 3500 -O-H -CEN N-H CO I, I =C H 2730- 2820 道 H 3000- 2 peaks 3100 -C-H 2850- 2960 0 -C-O-H broad-3000 3000 usually strong -CEN B 2200 -CICH 3 2200 2500 wavenumber, cm-¹ 2000 C C HC N 1680 OR 1730 200 C. H 1600- 1660 0.585 1710 C. NA₂ 1650 3 1600 O 1500 *** 1000Signal b in the spectrum for 2-ethoxyethyl acetate ( comes from the Hs connected to: O C4 C1 C3 O C2 O C5 PPM G11C2 CA C5How many non-equivalent proton signals are expected in chloroethene (shown)? CI H H H
- Assign the peaks in the spectrum to the functional groups in n-butyl acetate. Microns (µm) 2.5 3.0 3.5 4.0 5.0 6.0 8 10 15 20 100 a 2787 cm-1 1083 cm-1 2965 cm- 1742 cm 1246 cm-1 4000 3500 3000 2500 2000 1500 1000 500 Wavenumber (cm1) C=O peak =| С-Н рeak C-O peak Submit Transmittance (%)Select the functional group represented in the following IR spectrum. LOD TRANSMITTANCEI D 4000 O aldehyde carboxylic acid ketone O alcohol ester 3000 2000 HAVENUMBERI-I 1500 1000 500Into how many peaks will each of the circled protons be split? (Assume complete resolution of all NMR peaks is possible) CI CH3 H H₂C OH H H 1 Br H Multiple Choice 11 1=2; 11= 6; 111=4 1=2, 11=7; 11=4 1=2, 11 = 7, 11=3 1= 3,11 = 7, 111=4 III -CH3 H *** Next
- For the following 9 compounds (most of which were the ones used in this lab), tell me what peaks you would expect to see in the 'H-NMR spectrum of those compounds. I have provided table for you to fill out with approximate chemical shift (ppm units), peak multiplicity_(singlet, doublet, etc.) and integration of the signal (how many protons would give that signal). No IR data is required. In addition, tell me the number of 13C-NMR signals you would expect to see [specific 13C shifts are not required] PredictWhich of the following is the best prediction of the chemical shifts for the signals in the H NMR spectrum for the following compound? O O A B. C. D. 1=0.9 ppm, 11-2.7 ppm, Ill-1.2 ppm, IV-0.9 ppm 1-1.1 ppm, 11-3.2 ppm, Il-1.4 ppm, IV-0.9 ppm 1-0.9 ppm, 11-1.7 ppm, Il-1.2 ppm, IV 1.1 ppm 1-0.9 ppm, 11-1.9 ppm, III-3.4 ppm, IV-0.9 ppm IV 1024 xAssign all of the signals in the ¹H NMR spectrum for propyl acetate. Fill in the table below with the 'H NMR data. Number each proton (or set of protons) to match the corresponding peak in the NMR. Integration Splitting Propyl acetate structure with protons labeled Signal - Chemical shift (ppm) 1 2 3 4 11 propyl acetate 10 9 8 7 6 5 ppm 2H, triplet 4 3 3H, singlet 3H, triplet 2H, sextet 2 1 Figure 3.7 ¹H NMR spectrum for propyl acetate. 0