The following spectral data are provided for a compound with a molecular formula CHaNO;: IR (solution in CHCI), 500 MHz 'H NMR, 125.8 MHz "C NMR, DEPT-90, DEPT-135, COSY, HMQC, HMBC, TOCSY (150 ms mixing time) and NOESY. Also included are select regions of the HSQC-TOCSY spectra with increasing mixing times. All NMR spectra were measured in CDCI, solution. Using these data, determine the structure of the compound and assign all of the H and C resonances to their respective atoms in the structure. Make sure to determine the stereochemistry of the compound and to clearly assign 'H resonances to the appropriate diastereotopic protons.

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Question 5
The following spectral data are provided for a compound with a molecular formula CHNO: IR (solution in
CHCI), 500 MHz 'H NMR, 125.8 MHz °C NMR, DEPT-90, DEPT-135, COSY, HMQC, HMBC, TOCSY
(150 ms mixing time) and NOESY. Also included are select regions of the HSQC-TOCSY spectra with
increasing mixing times. All NMR spectra were measured in CDCI, solution. Using these data, determine the
structure of the compound and assign all of the H and C resonances to their respective atoms in the
structure. Make sure to determine the stereochemistry of the compound and to clearly assign 'H resonances
to the appropriate diastereotopic protons.
Transcribed Image Text:Question 5 The following spectral data are provided for a compound with a molecular formula CHNO: IR (solution in CHCI), 500 MHz 'H NMR, 125.8 MHz °C NMR, DEPT-90, DEPT-135, COSY, HMQC, HMBC, TOCSY (150 ms mixing time) and NOESY. Also included are select regions of the HSQC-TOCSY spectra with increasing mixing times. All NMR spectra were measured in CDCI, solution. Using these data, determine the structure of the compound and assign all of the H and C resonances to their respective atoms in the structure. Make sure to determine the stereochemistry of the compound and to clearly assign 'H resonances to the appropriate diastereotopic protons.
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