3-4-5

4. For each pair of compounds, identify ow you would distinguish them using either 1H NMR spectroscopy or 13C NMR spectroscopy: (a) (b) (c) (d) 5. For each compound shown below, (1) Sketch the spectrum 13C NMR spectrum (totally decoupled, with a singlet for each type of carbon), showing approximate chemical shifts. (2) Show the multiplicity expected for each signal in the off-resonance-decoupled spectrum. (a) (b) H2C=CHCH2Cl ethyl acetate 3-chloropropene (d)