NMR Experiment A Spectroscopy I 1H NMR Guidelines and Tips 1. 1H NMR peaks should be labeled using letters (a, b, c, etc.), starting with the peak that is the most downfield (highest ppm). 2. When labeling peaks, don’t mistake residual solvent peaks or the TMS peak for a signal (peak) from the sample. a. 1H NMR: singlet at 7.26 ppm due to residual CHCl3 from CDCl3 (solvent); singlet at 0 ppm due to TMS. 3. Chemical shifts (δ) should be reported as the center of the peak set. For peaks with odd multiplicities (triplet, quintet, etc.), the chemical shift is that of the middle peak. For peaks with even multiplicities (doublet, quartet, etc.), the chemical shift is reported as the average of the two central most peaks. 4. The peak labels in the expanded regions are in hertz (Hz) for assigning coupling constants. a. The coupling constant (J) for a given multiplet is equal to the distance, in Hz, between adjacent peaks. 5. Integral values are proportional to the number of hydrogens represented by a given peak. 6. Use the following abbreviations for peak multiplicities. For our purposes, a multiplet (m) is a peak that cannot be assigned a simple, first-order splitting pattern (i.e., not a singlet, doublet, triplet, etc.) singlet (s) quartet (q) octet (oct) doublet (d) quintet (quint) nonet (non) triplet (t) sextet (sext) multiplet (m) 7. Degrees of unsaturation (DOU) is calculated as: where C is the number of carbons, H the number of hydrogens, N the number of nitrogens and X the number of halogens. 8. Work your way through the following problems and record your answers in the answer pack. DOU2C 2  H N X21. For each of the following compounds, give the number of signals (resonances) that you would expect to find in the 1H NMR spectrum. a. b. 2. For each of the following compounds, give the multiplicity (s, d, t, etc.) and the number of protons (relative integrations) for each type of proton indicated. Be sure to give the integration value for the entire set of protons that are of the type indicated. 3. Give the chemical shifts, multiplicities and coupling constants for each of the peaks in the 1H NMR spectrum shown below (taken on a 300 MHz spectrometer). 4. Use the information from question #3 to assign the chemical shift of each peak to the appropriate set of protons in the following molecule. OOHHOOOabcdNHOefghiOOClac ebd5. Complete the spectroscopy data table in the answer pack using the 1H NMR spectrum (shown below) for the following compound. 6. Complete the spectroscopy data table in the answer pack using the 1H NMR spectrum (shown below) for the following compound. NO21H NMR, 300 MHz NCCN 1H NMR, 300 MHz7. Complete the spectroscopy data table in the answer pack using the 1H NMR spectrum (shown below) for the following compound. 8 Complete the spectroscopy data table in the answer pack using the 1H NMR spectrum (shown below) for the following compound. OO1H NMR, 300 MHz OOO 1H NMR, 300 MHz9. Complete the spectroscopy data table in the answer pack using the 1H NMR spectrum (shown below) for the following compound. OHOBr1H NMR, 300