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1) How could the pair of structures shown be distinguished using IR spectroscopy? List the diagnostic peaks in wave numbers that would be present or absent for each pair. (a) (b) H3C H H CH3 OCH3 CH3 N CH3

There are four isomers shown below (compounds A-D). TWO of these isomeric nitrogen- containing compounds were extracted and isolated from tobacco leaves. Their structures were determined using 1H NMR. These two 1H NMR spectra are shown below. Make peak assignments of the NON-AROMATIC signals to determine which TWO isomers are represented. Use the specific labels (a-h) provided with spectra.

1. Draw all possible isomers for the molecular formula C6H14 Next predict mass spectra of all isomers and explain how you would use mass spectra to identify each of the isomers.