!" !"#!!() A c O b N Ha e d N-(2-methoxyethyl)methylamine C4H11NO (MW = 89), Nitrogen rule (odd) B d c b c OH a d c 3-phenyl-2-propyn-1-ol C9H8O (MW = 132) C a b d c Br e 3-bromo-o-xylene C8H9Br (MW = 184), Br isotope D O O f e O d b c a ethyl 2-ethyl-3-oxobutyrate C8H14O3 (MW = 158) E O b c a OHd Cl (R)-2-chlorobutyric acid C4H7ClO2 (MW = 122), Cl isotope F c O e d b a f O 3,4-dihydro-2H-1-benzopyran-4-one C9H8O2 (MW = 148) G O i O h i g Hf d g He c b a cis-3-hexenyl benzoate C13H16O2 (MW = 204) δH 3.5 (He, 2H, t), δH 3.4 (Hd, 3H, s), δH 2.7 (Hc, 2H, t), δH 2.4 (Hb, 3H, s), δH 2.2 (Ha, 1H, exchange) δH 7.4 (Hd, 2H, d), (d, long range), δH 7.3 (Hc, 3H, m), δH 4.5 (Hb, 2H, s) , δH 3.6 (Ha, 1H, exchange) δH 7.3 (He, 1H, d), (d, long range), δH 7.1 (Hd, 1H, d), (d, long range), δH 6.9 (Hc, 1H, dd), δH 2.3 (Hb, 3H, s), δH 2.3 (Ha, 3H, s) δH 4.2 (He, 2H, q), δH 3.3 (Hd, 1H, t), δH 2.2 (Hd, 3H, s), δH 1.9 (Hc, 2H, dq), δH 1.3 (Hb, 3H, t), δH 0.9 (Ha, 3H, t) δH 9.4 (Hd, 1H, exchange), δH 4.3 (Hc, 1H, d), δH 2.1 (Hb, 2H, dq), δH 1.1 (Ha, 3H, t) δH 7.8 (Hf, 1H, d), (d, long range), δH 7.4 (He, 1H, dd), (d, long range), δH 7.0 (Hd, 1H, dd), (d, long range), δH 6.9 (Hc, 1H, d), (d, long range), δH 4.5 (Hb, 2H, t), δH 2.8 (Ha, 2H, t) δH 8.0 (Hi, 2H, d), (d, long range), δH 7.5* (Hh, 1H, t), (t, long range), δH 7.5* (Hg, 2H, dd), δH 5.5 (Hf, 1H, dt, J = 10.0 Hz, J = 6.8 Hz), (t, long range), δH 5.4 (He, 1H, dt, J = 10.0 Hz, J = 6.9 Hz), (t, long range), δH 4.3 (Hd, 2H, t), δH 2.5 (Hc, 2H, tq), (d, long range), δH 2.1 (Hb, 2H, dq), (d, long range), δH 1.0 (Ha, 3H, t) * 7.5 ppm, 3H, –1– 3338 N–H 2930 C(sp3)–H 2883 C(sp3)–H 1470 CH3 bending 1450 CH3 bending 1106 C–O or C–N 3336 (broad) O–H 3058 C(sp2)–H 2918 C(sp3)–H 2239 C≡C 1598 C6H4 1498 C6H4 1033 C–O 3049 C(sp2)–H 2946 C(sp3)–H 1561 C6H3 1465 CH3 bending 1452 CH3 bending 699 C–Br 2973 C(sp3)–H 1739 C=O 1717 C=O 1252 C=O+– 1053 C–O 1026 C–O 3300–2500 CO2H 2978 C(sp3)–H 1725 C=O 1205 C=O+– 827 C–Cl 3069 C(sp2)–H 2986 C(sp3)–H 1697 C=O 1604 C6H4 1479 C6H4 1256 C=O+– 1039 C–O 3012 C(sp2)–H 2964 C(sp3)–H 1720 C=O 1603 C=C 1585 C6H5 1452 CH3 bending 1271 C=O+– 1071 C–O
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