Use the following MS, IR, 1H and 13C NMR spectral data to identify the compound,

Question

Use the following MS, IR, 1H and 13C NMR spectral data to identify the compound, which contains three oxygen atoms, explaining your answer. (A fully detailed explanation would be greatly appreciated)

MS (EI) m/z 151 (9), 150 (96, M+), 149 (100), 121 (27), 91 (10), 65 (15), 63 (24), 39 (6)
IR (liquid film); 2899 (w), 2827 (w), 2733 (w), 1697 (s), 1605 (m), 1489 (m), 1449 (s), 1260 (s),

1042 (m) cm-1
1H NMR (CDCl3, ppm) 9.80 (s, 1H), 7.40 (dd, 1H, 3J = 8.1 Hz, 4J = 1.7 Hz), 7.32 (d, 1H, 4J =

1.7 Hz), 6.92 (d, 1H, 3J = 8.1 Hz), 6.07 (s, 2H) ppm
13C{1H} NMR (CDCl3, ppm) 190.2, 153.0, 148.6, 131.8, 128.6, 108.3, 106.8, 102.1 ppm

Explanation / Answer

IR show band at 1697 cm-1 is due to carbonyl group, band at 2899, 2827 and 2733 cm-1 is due to CH streaching

1H NMR has singlet at 9.8 ppm is due to aldehyde group

Peak at 7.4, 7.32 and 6.92 ppm is due to aromatic hydrogen

Peak at 6.07 ppm is due to methylene group in between two oxygen

13C NMR show 8 signal show the presence of 8 carbons

Therefore the name of the compound for the above spectroscopic data is

2H-1,3-benzodioxole-4-carbaldehyde

For structural representation of the compound go the below mentioned link

www.chemspider.com/Chemical-Structure.74240.html

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