Determine the structural formula for the compounds whose H NMR spectra is given. They were all run at 300 MHz.

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Problem 3.4 A 2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 1.0 0.9 0.8 ppm Problem 3.4 B OH wellen 1 3.5 3.0 2.5 2.0 1.5 1.0 ppm Problem 3.4 C 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 ppm Problem 3.4 D hu 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm Problem 3.4 E wille 2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 1.0 0.9 0.8 ppm Problem 3.4 F X4 12.0 11.5 ppm 3.5 3.0 2.5 2.0 1.5 ppm Problem 3.4 G 2.7 2.6 2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 1.0 0.9 0.8 ppm Problem 33.4 H 4.4 4.2 4.0 3.8 3.6 3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 ppm Problem 3.4 1 - 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm Problem 3.4 J WA al 2200 2150 2100 Hz 1250 1200 1150 Hz 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 ppm Problem 3.4 K 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm Problem 3.4 L elle 3.5 3.0 2.5 2.0 1.5 1.0 ppm Problem 3.4 M 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm Problem 3.4 N a pyrazine M 2520 2510 2500 2490 Hz 8.5 8.0 7.5 7.0 6.5 1 4.0 6.0 5.5 5.0 4.5 3.5 3.0 ppm Problem 3.40 1 proton (x32) 13 12 ppm 2300 2250 2200 2150 Hz frin 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 ppm Problem 3.4 P. 8.2 8.1 8.0 7.9 7.8 7.7 7.6 7.5 7.4 7.3 ppm Problem 3.4 Q 1 proton (32) X un 12 11 ppm 4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm Problem 3.4 R 7 3.6 3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 ppm Problem 3.4 S Unsaturated ketone 1520 1510 1500 Hz 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm Problem 3.4 T 13 12 ppm 2.8 2.6 2.4 2.2 2.2 2.0 1.8 1.6 1.4 1.2 1.0 ppm Problem 3.4 U 7.5 7.4 7.3 7.2 7.1 7.0 6.9 6.8 6.7 6.6 6.5 6.4 6.3 6.2 6.1 6.0 5.9 5.8 5.7 ppm Problem 3.4 V JU 2120 2100 2080 2060 Hz S 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 ppm Problem 3.4 W Unsaturated ketone 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 ppm