Compound With a Molecular Formula & Spectral Data - IT Assignment Help

Assignment Task

Task    

The following spectral data are provided for a compound with a molecular formula C15H22O2: IR (Thin Film on NaCl), 500 MHz 1 H NMR, 125.7 MHz 13C NMR, DEPT-90, DEPT-135, COSY, HMQC, HMBC, TOCSY and NOESY. Using these data, determine the structure of the compound and assign all of the 1 H and 13C resonances to their respective atoms in the structure. Make sure to determine the stereochemistry of the compound and to clearly assign 1 H resonances to the appropriate diastereotopic protons. All NMR spectra were measured in CDCl3. The 1 H resonance at 7.25 ppm corresponds to CHCl3.

b. Tabulate the shifts of the 1
H resonances (a-i) in order of descending chemical shift. Provide an appropriate name for each multiplet (e.g., s, d, t, q, quintet, sextet, septet, octet, dd, ddd, dt, td, dddd, tt, qd, dq, etc.) and list its coupling constants in appropriate order; also list its integral [e.g., a: 3.30 (t, J = 7.3 Hz, 3 H)]. If a resonance is not described by a well-defined multiplet, name it as m and give its range [e.g., c: 4.43-4.37 (m, 2 H)].
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c. Redraw the structure of the molecule below and write the letter (a-i) of each 1 H resonance next to the proton or protons to which it corresponds. If the assignment of a particular resonance is uncertain, please indicate this

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