5) 1Η NMR 1H NMR Spectrum (400 MHz, CDCI, solution) expansions expansion 5.0 4.8 ppm 1.6 1.4 ppm Exchanges with D20 7.5

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5) 1Η NMR 1H NMR Spectrum (400 MHz, CDCI, solution) expansions expansion 5.0 4.8 ppm 1.6 1.4 ppm Exchanges with D20 7.5 7.3 ppm TMS 1 1 1 1 10 9 8 7 6 5 4 3 2 1 0 8 (ppm) a) What does "exchanges with D20" mean and what does it tell you about the proton that corresponds to this signal? Is this consistent with any other information you have about the structure? b) Use a ruler to measure the height of the integration lines on the spectrum and calculate the relative intensities (how many protons does each signal correspond to) of each signal. Check using the molecular formula that you have accounted for all protons in the molecule. c) What do the chemical shifts of the various signals tell you about the protons that correspond to each signal? d) Use the multiplicity of the signals in the spectrum to formulate fragments of the molecule that are consistent with these splitting patterns.