Question

H2 Ha a) Given that the 'H NMR spectrum was acquired at 300 MHz, convert the ppm values for the alkenyl region to Hz and provide the cis proton coupling constant to 1 decimal place. CEC Ha OH b) Please provide the chemical shift values for i) Both alkyne carbons i) The aromatic carbon bearing the substituent ii)H iv) H v) H vi) H H NMR spectrum as 25 1C NMR spectrum 9911 1C NMR spectrum 90 60 10 170 160 150 140 130 120 110 100 n (ppm) !! OCT9- H NMR spectrum 7,50 7,45 7.40 7.35 f1 (ppm) 7,30 6.0 5.8 5.6 5.4 5 7 f1 (ppm) 9.0 3.0 1.0 0.5 8 5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 2.5 1.5 f1 (ppm) 7.49 7.47 94 156'I 96'2 7.34 7.34 7.33 7.31 7.485 7.480 7.467 17.456 II'9 80'9 40'9 S09 F00 ES'S o0' 960 5.28 5.14 7.344 r7.327 7.325 7.311 ZI'S 6.141 ZOI'9 6.085 490'9 S09 6.033 86'T 06S'S- ZIE'S 8225 5.139 5.123 H NMR spectrum 7,50 7,45 7.40 7.35 f1 (ppm) 7,30 6.0 5.8 5.6 5.4 5 7 f1 (ppm) 9.0 3.0 1.0 0.5 8 5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 2.5 1.5 f1 (ppm) 7.49 7.47 94 156'I 96'2 7.34 7.34 7.33 7.31 7.485 7.480 7.467 17.456 II'9 80'9 40'9 S09 F00 ES'S o0' 960 5.28 5.14 7.344 r7.327 7.325 7.311 ZI'S 6.141 ZOI'9 6.085 490'9 S09 6.033 86'T 06S'S- ZIE'S 8225 5.139 5.123 1C NMR spectrum 170 160 150 140 130 120 110 100 90 80 70 60 50 f1 (ppm) 136.91 131.75 T 128.61 128.32 122.37 116.66 87.67 20 86.33 -63.70

Answer 1

iven: He EC H (C-1) tenutrt alrfon pm nto t at 300 L0 chemical shist (6) 9n PPm XID Specthrundte rquanty In the H NMR Spehum alion prtun (a) apptars in therange 5-1 PPM= n H 30DX186 c 1530 H Wdd l9 5.1 X300 11 bor 6.3 PPm- H xI 510tt 1510 H, - 3 00Xub ty f0 H 5.5 PPM Al 1650 H 650 300 Xm Υ Η IS0 H (t830 1 3 33 PPM -CEC 4 C,- 86.33 Ppm H 63-70 PpM 4 4 136.91 PPM 5 C 6-6 PPM 1ag. 2 PPM 131. PM C7 122. 3 ?Pm. CA