An unknown compound has a molecular formula of C4H₂O. Its IR spectrum shows prominent absorptions at 3061, 2988, 1720, and 1680 cm It exhibits the following signals in its 'H NMR spectrum (ppm): 2.29 (singlet, 3H), 5.91 (doublet of doublets, 1H), 6.21 (doublet of doublets, 1H), 6.30 (doublet of doublets, 1H); and the following signals in its 13C NMR spectrum (ppm): 27.2, 127.8, 136.4, 197.7. Draw the structure of the unknown compound.

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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
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An unknown compound has a molecular formula of C4H6O. Its IR spectrum shows prominent absorptions at 3061, 2988, 1720, and 1680 cm . It exhibits
1
the following signals in its H NMR spectrum (ppm): 2.29 (singlet, 3H), 5.91 (doublet of doublets, 1H), 6.21 (doublet of doublets, 1H), 6.30 (doublet of
13
doublets, 1H); and the following signals in its
C NMR spectrum (ppm): 27.2, 127.8, 136.4, 197.7.
Draw the structure of the unknown compound.
1
Click and drag to start drawing a
structure.
0
X
E
0
E
E
C
Transcribed Image Text:An unknown compound has a molecular formula of C4H6O. Its IR spectrum shows prominent absorptions at 3061, 2988, 1720, and 1680 cm . It exhibits 1 the following signals in its H NMR spectrum (ppm): 2.29 (singlet, 3H), 5.91 (doublet of doublets, 1H), 6.21 (doublet of doublets, 1H), 6.30 (doublet of 13 doublets, 1H); and the following signals in its C NMR spectrum (ppm): 27.2, 127.8, 136.4, 197.7. Draw the structure of the unknown compound. 1 Click and drag to start drawing a structure. 0 X E 0 E E C
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