3. Answer the following question for the natural product ambroxide (C16H28O). The H1, C13, DEPT, HMQC, HMBC spectra are problem 7.8 in your textbook. The COSY is attached. (22 points total) 2 1 CHs 13 9 12 Label the peaks by writing the number of the H or C ABOVE the peaks. a.) Label the methylene carbon peak for C1 and the hydrogen peaks on C1 on the spectra below. (4 pts) b.) Label the methyl carbon peak for C13 and the hydrogen peaks on C13 on the spectra below. (4 pts) c.) Label the methine carbon peak for C9 and the hydrogen peaks on C9 on the spectra below. (4 pts) d.) Label C12 on the 13C spectrum below. (2 pts) e) Label C3 on the 13C spectrum below. (2 pts) (-)-ambroxide CH H3C CH₂ CH اللمساس 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm 80 75 70 65 60 60 55 50 45 40 35 30 25 20 15 ppm f.) On the HMQC spectrum below, identify the carbon atoms that contain diastereotopic hydrogens. (6 pts) Draw a line (be exact) showing the correlation of the C with its diastereotopic hydrogens. F2 (ppm) 1.5 2.01 2.5 pr 3.0 3.5 4.0 65 60 55 50 45 40 35 30 25 20 F1 (ppm) -- 5 roximal plateral ranspor cin is a GLT2 fe of L Alct. Ic COSY F2 (ppm) 1.5 10 2.0 2.5 3.0 3.5 3.5 3.0 2.5 2.0 1.5 1.0 F1 (ppm) 6