Problem #10: The molecular formula for an unknown compound is C7H5OBr. Data for the 1H NMR, 13C NMR, infrared and mass spectra for this compound are available by clicking on the buttons below; use the "Return" button to return to this screen. Help with the interpretation of each spectrum is available and you can review background and selected correlation tables by clicking on the links in the MENU above. Using the spectral and analytical information provided, determine the structure for this compound.



















 

NMR Spectrum
Problem #10: C7H5OBr



















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Problem #10: C7H5OBr



















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Problem #10: C7H5OBr




















13C NMR: two singlets: 103, 137.4; four doublets: 133.2, 134.0, 129.7 and 137.8 ppm doublet: 190.0 ppm

Problem #10: C7H5OBr



















  • The molecule contains both oxygen and bromine, and from the analysis, contains five double bonds or rings. The large number of degrees of unsaturation strongly suggests an aromatic compound (DU = 4).
  • The mass spectrum displays a molecular ion, an m-1 peak and a peak corresponding to loss of a CHO unit. The strong m-1 peak is also suggestive of an aldehyde.
  • The 13C spectrum contains seven peaks, indicating that the molecule has no symmetry. The peaks in the aromatic region strongly suggest 1,3-disubstitution, and there is a singlet at d 190 which would be consistent with a aldehyde carbon.
  • The proton NMR also shows evidence for an aldehyde CH and the complex splitting pattern in the aromatic region is consistent with 1,2 or 1,3-disubstitution on an aromatic ring.
  • The IR shows sharp peaks for unsaturated (sp2) CH, a characteristic aldehyde CH stretch at around 2800 cm-1 and peaks consistent with double bond stretching.
  • The simplest structure which is consistent with all of these data would be a 1,2 or 1,3-disubstitution aromatic compound bearing bromine and aldehyde residues.