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BONUS (10 pts) Determine the compound structure based on the spectra below. Annotate spectra to receive full credit 3457 IR S
Q Search BC NMR Spectrum (100.0 MH, CDC, solution) DEPT CH CH cht profon decoupled 200 8 (ppm) TH NMR Spectrum (400 MHz, CDCI
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Answer #1

IR :

  • 3457 cm-1 : due to -OH stretching
  • 1671 cm-1 : due -C=O stretching ( indicates conjugated Carbonyl group)

UV : indicates n to pi* transitions.

Mass Spectra : molecular mass : m/z - 112

   using IR and mass spectra possible Molecular Formula : C6H8O2.

13C-NMR :

6 peak at 24 ppm, 25 ppm, 37 ppm (Sp3 C) ; 120 ppm,149 ppm (sp2 C) , 198 ppm (carbonyl). 13C-DEPT indicates 3*-CH2- grops, 1 '-CH-' group and other 'Cs' without Hs.

1H-NMR :

2.0 ppm ( 2H, quintet) ,2.4 ppm ( 2H, quartet) , 2.53 ppm ( 2H, triplet) , 6.14 ppm (1H - alkenic H ). -OH is exchanged with D2O.

    Most probable structure :

             2-hydroxy-2-cyclohexen-1-one

о ОН

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