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Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

ChapterL4: Proton (1h) Nmr Spectroscopy

Section: Chapter Questions

Problem 4CTQ

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Question

Imagine that you analyzed the original distillation mixture from Exp #3 using a Gas Chromatography instrument that is equipped with both a Flame Ionization Detector (FID) and a Mass Spectrometer (MS). Use the “GC-FID/MS Template” provided in the Experiment folder (if you cannot print it or annotate it, then you may hand-draw the template and your answers on a piece of paper). For this question, and this question only, you may very neatly hand-

draw or use ChemDraw to add structures to the spectra

i) On the “GC-FID/MS Template,” draw the FID spectrum for the Exp #5 original mixture. Assume that the compounds elute from the column at 5.13 minutes, 7.61 minutes, and 10.43 minutes. Clearly label each signal with the corresponding compound name. Signals should not be drawn as more than “30 seconds wide.” Each signal should include a retention time below the signal (as described above).

ii) On the “GC-FID/MS Template,” draw the molecular ion isotope pattern that corresponds to the compound eluting at each of the given retention times for which there is a signal in the FID spectrum. Clearly correlate the FID signal with the MS spectrum by labeling both with a specific retention time. Clearly label the X-axis at every signal location. In

each of the three mass spectra include only the molecular ion isotope pattern (no fragmentation patterns for this problem). Include isotope signals that result from any atom that has a natural abundance of 1% or greater. Signal

intensities (height) should be labeled [the absolute value of the largest signal is not critical (rescale to 100% if you

wish, or not). The most important is that the relative intensities of signals are correct].

iii) Clearly draw the complete chemical structure and specify important distinguishing isotopes for every signal in all of the mass spectra. All “C” is assumed to be12C, and all “H” is assumed to be “1 H” but no other assumptions are made with regards to isotopes. If a molecule contains multiple C atoms but only one is13

C, then you should write, “Molecule contains one13 C atom” below the structure (do not simply label one of the many C as13 C, as this does not indicate the same thing). All other isotopes in the molecule mustbe labeled on the atom. To be clear, you will includeone structure for each of the isotope signals in a mass

spectrum (so likely multiple structures drawn on eachmass spectrum).

- answer using sheet attached, thank you!