A pathologist was given a sample of a white tablet found at the scene of a suicide. In order to complete her report the pathologist received an NMR spectrum of the sample (Figure 29.20a) and information from the police that the tablets involved were either aspirin or paracetamol. The displayed formulae of both drugs are also shown in Figure 29.20b.

a. Using this information, which drug was in the white tablet? Explain your answer.

b. Sketch the NMR spectrum you would expect to see if the other drug had undergone NMR analysis. Label each peak with its relative area and the type of proton that caused it.

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3H 1H 2H 2H 1H 10 9 8 7 6 5 4 3 2 1 0 Chemical shift, 8/ ppm 11 b H H H. H H H H- C-C-H H H H aspirin paracetamol Figure 29.20 a NMR analysis of the unknown drug sample. b Aspirin and paracetamol. Absorption of energy