Question

^{3.60 3.58 3.56 3.54 3.52 f1 (ppm) 3.50 3.48 3.46 C (dd) 7.34 7.45 7.40 7.35 7.30 7.25 i (ppm) 7,20 7.15 7.10 B (dd) A (dt) 7.39 7.20 D (t) 4.83 E (dd) 3.53 T T 1.98 1.93 4.00 2.09 2.01 .8 7.6 7.4 7.2 7.0 6.8 6.6 6.4 6.2 6.0 5.8 5.6 5.4 f1 (ppm) 5.2 5.0 4.8 4.6 4.4 4.2 4.0 3.8 3.6 3.4 3. diels-alder-product PROTON 02 70 % yield 7.41 7.40 7.39 7.38 7.35 7.34 7.34 7.33 7.26 cdcl3 7.22 7.21 7.21 7.20 0ZL SI'L 560 4.84 4.83 4.83 r3.54 3.53 3.52}

^{Match the peaks labeled A,B,C,D,E to the Diels-Adler product and what part of the products structure creates each peak on the NMR graph.}

Answer 1

HD E: 3.53ppm, 2H (dd): The most upfield alkyl protons, they have only one direct coupling partner, however signal is dd hence it must be due to long range coupling. D: 4.83ppm, 2H(t): the B-protons hence down field alkyl protons. Has two coupling partners. A: 7.20ppm, 4H(dt): aromatic protons has ortho as well as meta coupling partners. B: 7.34ppm, 2H(dd): from the ring which is close to anhydride ring has anisotropic effect. C: 7.39ppm, 2H(dd): from the ring which is away from the anhydride ring and has ortho as well as meta coupling. No anisotropic effect.