The IR and 1H NMR spectra of phenacetin (C10H13NO2) are given in Fig. 17.7. Phenacetin is an analgesic and antipyretic compound and was the P of A-P-C tablets (aspirin-phenacetin-caffeine). (Because of its toxicity, phenacetin is no longer used medically.) When phenacetin is heated with aqueous sodium hydroxide, it yields phenetidine (C8H11NO) and sodium acetate. Propose structures for phenacetin and phenetidine.

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7.4 72 7.0 6.8 4.0 3.8 1.4 1.2 TMS Impurity SH (ppm) 100 90 70 60 50 40 F 30 20 10 4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 650 Wavenumber (cm-y