Compound E (C8H10O2) is a neutral solid. Its mass spectrum

Chapter 21, Problem 21.22

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Compound E (C8H10O2) is a neutral solid. Its mass spectrum shows a molecular ion at m/z 138 and prominent peaks at M-1 and M-17. Following are IR and 1 H-NMR spectra of compound E. Deduce the structure of compound E. 0 100 10 20 30 40 50 90 60 70 80 4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 2.5 3 4 5 6 7 8 109 11 12 1413 15 20 Transmittance (%) Wavenumber (cm1) Micrometers Compound E. 892 Chapter 21 Benzene and the Concept of Aromaticity 10 9 8 7 6 5 4 3 2 1 0 ppm Chemical Shift ()

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