Central Washington University NMR and Mass Spectrum Questions

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Central Washington University

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NMR Spectra from two isomers A and B, both with molecular formula C4H-BrO2 are given below. One isomer is an alkene, the other is an ester. Identify which is which and then propose structures for both, briefly justifying your decisions. Note: • TH peak multiplicities and 13C DEPT information are given beneath the respective spectra. • The signal at 3.05 ppm in the TH spectrum of isomer B disappears after shaking with a few drops of D20. The data is consistent with TWO similar structures for A and for B. You only need to provide one structure for A and one for B. 13C A COCI ppm 100 50 DEPT 150 +1 absent 9 8 7 6 5 3 2 4 9 s ppm 13C CDCI B 100 50 150 DEPT ppm 8 8 6 5 N 2 3 s ppm d d An unknown compound containing only C, H and O gave the following mass spectrum: 100 80 60 Relative Intensity /z 51.0 77.0 105.0 134.0 135.0 intensity 12.9 42.7 100.0 14.3 1.4 40 20 operty th 50 100 125 m/z Interpret the information from the mass spectrum to determine the molecular formula and to identify tell-tale fragments. Propose a structure for the molecule briefly justifying your decision.
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