Question:

a. Propose a structure for the compound.

b. Assign the 1H NMR and 13C NMR spectra for each compound

On the next four pages are MS, IR, and ¹H and ¹³C NMR spectra of compounds A, B, C and D. The molecular formulas are given. Use these spectra to propose structures forA, B, C and D. For each compound do the following:

a. Propose a structure for the compound.

b. Assign the ¹H NMR and ¹³C NMR spectra for each compound.

Note: if you are not confident with your proposed structure, try your best to identify as many as possible functional groups (fragments) on MS, IR, ¹H NMR and ¹³C spectra to gain credits.

Compound A (C₇H₁₂O)

(1) Mass Spectrum

(2) IR Spectrum

(3) ¹H NMR Spectrum

(4) ¹³C NMR Spectrum

Compound B (C₅H₈O)

(1) Mass Spectrum

(2) IR Spectrum

(3) ¹H NMR Spectrum

(4) ¹³C NMR Spectrum

Compound C(C₉H₁₄O)

(1) Mass Spectrum

(2) IR Spectrum

(3) ¹H NMR Spectrum

(4) ¹³C NMR Spectrum (in CDCl₃)

Compound D(C₁₂H₁₈O)

(1) Mass Spectrum

(2) IR Spectrum

(3) ¹H NMR Spectrum

(4) ¹³C NMR Spectrum