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Study Notes

From what we have learned about ¹H NMR spectra so far, we might predict that the spectrum of 1,1,2-trichloroethane, CHCl₂CH₂Cl, would consist of two peaks—one, at about 2.5-4.0 δ, expected for CH₂-halogen compounds and one shifted downfield because of the presence of an additional electronegative chlorine atom on the second carbon. However, when we look at the spectrum it appears to be much more complex. True, we see absorptions in the regions we predicted, but these absorptions appear as a group of two peaks (a doublet) and a group of three peaks (a triplet). This complication, which may be disturbing to a student who longs for the simple life, is in fact very useful to the organic chemist, and adds greatly to the power of NMR spectroscopy as a tool for the elucidation of chemical structures. The split peaks (multiplets) arise because the magnetic field experienced by the protons of one group is influenced by the spin arrangements of the protons in an adjacent group.

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Spin-spin coupling is often one of the more challenging topics for organic chemistry students to master. Remember the n + 1 rule and the associated coupling patterns.