2444-090911

2444-090911 - QUIZ 1 Avg. 19.1 / 25 Stnd. Dev. 6.5 NH 2 CH...

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Unformatted text preview: QUIZ 1 Avg. 19.1 / 25 Stnd. Dev. 6.5 NH 2 CH amines 1-aminopentane NH 2 NH CH N- methylaminocyclopentane N CH 3 H 1 and 2 Amines No NH CH A 3 amine tripropylamine N Other functional group information will be introduced as we discuss the chemistry IMPORTANT: Only use the IR to identify the functional group. It is possible to do more, but for now we will only ID the functional group. 3 Amine The Real Way MS and IR Data is Reported 4-(2-Iodovinyl)-5-[3-(4-methoxybenzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolane (12) . To a cooled (0 C), stirred solution of 11 (250 mg, 0.42 mmol) in CH 2 Cl 2 (15 mL) was added iodine (213 mg, 0.84 mmol). After 10 min at 0 C, the reaction mixture was diluted with CH 2 Cl 2 and washed with saturated Na 2 S 2 O 3 and 10% KF solutions, and brine. The organic layer was dried (Na 2 SO 4 ), ltered, and concentrated. Silica gel column chromatography of the crude product using petroleum ether/EtOAc (9.5:0.5) as eluent gave 12 (174 mg, 96%) as a yellowish oil. [ ! ] 25 D +7.6 (c 1.1, CHCl 3 ). IR (CHCl 3 ): 2946, 2932, 2856, 1612, 1513, 1465, 1372, 1174, 1092, 947 cm-1 . 1 H NMR (200 MHz, CDC l3 ): " 7.29 (d, J ) 8.6 Hz, 2H), 6.53 (d, J ) 8.7 Hz, 2H), 6.29 (m, 2H), 4.44 (s, 2H), 3.94-4.01 (m, 1H), 3.81 (s, 3H), 3.63-3.76 (m, 1H), 3.47 (t, J ) 5.8 Hz, 2H), 1.61-1.78 (m, 4H), 1.40 (s, 3H), 1.40 (s, 3H). 13 C NMR (75 MHz, CDCl 3 ): " 161.4, 147.6, 129.5, 128.6, 114.0, 101.7, 86.5, 81.6, 75.8, 74.3, 70.1, 56.2, 28.8, 26.2, 25.5. Anal. Calcd for C 18 H 25 IO 4 (432.29): C, 50.01; H, 5.83, I, 29.36. Found: C, 50.42; H, 5.75, I, 30.01. 2- endo -3,6-endo -Trimethyl-3- hydroxy-4-oxatricyclo-[5.2.1.0 2,6 ]decan-5-one (9). A solution prepared from 500 mg (2.57 mmol) of anhydride 8 and 100 mL of diethyl ether was cooled to -78 C; ethereal 1.10 M methyllithium (2.35 mL, 2.58 mmol) was added by syringe over a 5-min period. The reaction mixture was kept at -78 C with continued stirring for 30 min and then at room temperature for 30 min. It was poured into 50 mL of vigorously stirred, saturated aqueous NH 4 Cl; the two-phased mixture was separated, the aqueous phase was extracted with three 40 mL portions of ether, and the ethereal solutions were combined, washed with 40 mL of brine, dried, filtered, and concentrated by rotary evaporation. The resulting colorless oil was triturated with pentane to give 513 mg (95%) of intermediate 9 as a white solid. A sample recrystallized from ether- pentane gave long white needles: mp 171-172 C; IR (neat) 3590, 3400, 2970, 2940, 2900, 1755, 1140, 1085, 1040 cm 1 ; NMR " 3.10 (s, 1 H, OH), 2.25 (m, 2 H, 2 CH), 1.58 (8, 3 H, CH 3 ), 1.0-1.8 (m, 6 H, 3 CH 2 ), 1.16 (s, 3 H, CH), 1....
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2444-090911 - QUIZ 1 Avg. 19.1 / 25 Stnd. Dev. 6.5 NH 2 CH...

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