The three compounds below are major ingredients in pumpkin spice (a blend of cinnamon, ginger, nutmeg, and cloves). Eugenol is found in cloves, zingerone is found in dried ginger, and trans- cinnamaldehyde is found in cinnamon. НО. Das My H eugenol zingerone trans-cinnamaldehyde Match each compound to its ¹H NMR spectrum: This is is the 1H NMR spectrum of [Select] 1H 10 HO. 8 3H 6 PPM 4 3H 4H 3H 2

Construct a structure of the given 1H NMR data signals.A.  C4H11N 0.94 δ (3H, triplet) 1.50 δ (2H, sextet) 1.69 δ (1H, singlet) 2.40 δ (3H, singlet) 2.55 δ (2H, triplet)     B.  C9H11Br 2.15 δ (2H, quintet, J = 7 Hz) 2.75 δ (2H, triplet, J = 7 Hz) 3.38 δ (2H, triplet, J = 7 Hz) 7.22 δ (5H, multiplet)

10)Pyrrolium (1) and pyridinium (2) have markedly H different pK, values. Circle the compound with the lower pK₂ value. -N-H 11) The 1H NMR spectrum of phenol is shown below. Of note, the aryl proton signals resolve in this molecule. Assign protons to specific signals in the spectrum 8 7 6 H₂ H₁ 5 ppm H3 H₂ *CHCl3 2 H₁

There are four isomers shown below (compounds A-D). TWO of these isomeric nitrogen- containing compounds were extracted and isolated from tobacco leaves. Their structures were determined using 1H NMR. These two 1H NMR spectra are shown below. Make peak assignments of the NON-AROMATIC signals to determine which TWO isomers are represented. Use the specific labels (a-h) provided with spectra.