Chili peppers contain significant quantities of vitamins A, C, and E, as well as folic acid and potassium. They also contain small quantities of capsaicin, the fiery essence responsible for the “hot” in hot peppers. The pure substance is in fact quite dangerous: Chemists working with capsaicin must work in special filtered-air enclosures and wear full body protection. One milligram placed on the skin will cause a severe burn. Although capsaicin has no odor or flavor of its own, its pungency — in the form of detectable stimulation of the nerves in the mucous membranes of the mouth — can be detected even when the substance is diluted to one part in 17 million of water. The hottest peppers exhibit about 1/20th of this level of pungency. 

The structure of capsaicin is shown on p. 1028. Some of the data that were used in its elucidation are presented below. Interpret as much of this information as you can. 

MS: m/z = 122, 137 (base peak), 195 (tricky!), 305. 

IR: v = 972, 1660, 3016, 3445, 3541 cm^-1. 

¹H NMR: δ = 0.93 (6H, d, J = 8 Hz), 1.35 (2H, quin, J = 7 Hz), 1.62 (2H, quin, J = 7 Hz), 1.97 (2H, q, J = 7 Hz), 2.18 (2H, t, J = 7 Hz), 2.20 (1H, m), 3.85 (3H, s), 4.33 (2H, d, J = 6 Hz), 5.33 (2H, m), 5.82 (2H, broad s), 6.73 (1H, d, J = 9 Hz), 6.78 (1H, s), 6.85 (1H, d, J = 9 Hz) ppm.