Question

This is the Wittig reaction. Below I have the reaction performed. So first we have the IR of starting material and then the product, all the peaks for all IR. Please identify the peaks in all the IR. Please also explain the difference observed thank you!. For this reaction an NMR is also performed, have to label the H NMR based on the product formed also based on the values given have to determine if the product was cis -9-2( 2-phenylethyl)anthracene or trans -9-2( 2-phenylethyl)anthracene Please explain how you know and found using the values given. Lastly, the TLC performed is lab, interpret the TLC and state if your reaction was successful and how do you know. For the TLC, Spot A is the (benzyltriphenylphosphonium chloride). Spot B is (benzyltriphenylphosphonium chloride and product 9-(2-phenylethenyl)anthracene,  Spot C.is just product 9-(2-phenylethenyl)anthracene, Spot D is 9-anthraldehyde and product 9-(2-phenylethenyl) anthracene, SPOT E is just 9-anthraldehyde. Please explain if the TLC is successful or not. Please answer this question completely so I can understand it, it's one reaction with multiple parts thank you!

Figure 2: Rxn performed in lab. O) 9-(2-phenylethenyl)anthracene Ph,P-CH2-Ph NaOH, DMF CI O PPh3 benzyltriphenyl- phosphonium

R-NIDA-19569 KBR DIS HIT-NO-4785 SCORE6DBS-NO-7692 BENZ YLTRIPHENYLPHOSPHONIUM CHL ORIDE LP s00 1000 00D 100 HAVENUNEERI1 749 17 3182 70 2862 4 1466 72 034 6B 3068 68 | 2779 4 1437 9 1026 7D1 722 102 6 2 T00 1O 3009 64 1686 66 1167 6692 72 692 E 995 4g 디 583 23 2987 68 1574 6B 1161 S5 2864 36 1498 46 1154 7073509 4 E8 B 495 11 2963 49 1484 ED 111 10HIT-NO-4587 |SCORE- [ נ|SDBS-NO-7396 9-AN THRACENE CARBALDEHTDE R-NIDA 20004 KBR DIS 100 e000 1500 1000 500 3444 70 726 74 1403 79 10 5 3434 7011670 4 | 1340 79 901 531 731 3074 77 1625 65 1252 45 3063 74 664 49 1109 2 E4 74641 7 3027 フ丁 1523 66 1175 72 2159 77 | 14ธ 7D11165 53 040 79 | 591 70 2773 74 | ↓444 6D 1049 46 δ74 65 846 79 eJ 62 743 7 715 57 596 68 607 67Position: 877.91 Intensity. 75.764 Position: 912.01 Intensity: 88.199 Position: 952.20 Intensity: 84.642 Position: 964.82 Intensity: 77.377 Position: 985.89 Intensity: 89.544 Position: 1014.19 Intensity. 86.657 Position: 1075.40 Intensity 87.268 Position: 1151.77Intensity: 87.961 Position: 1177.96 Intensity 88.860 Position: 1202.67 Intensity: 88.890 Position: 1254.31 Intensity: 89.055 Position: 1285.19 Intensity 87.470 Position: 1330.29 Intensity: 88.350 Position: 1351.60 Intensity: 86.189 Position: 1385.35 Intensity: 89.306 Position: 1409.28 Intensity: 87.607 Position: 143806 Intensity: 85.022 Position: 1448.08 Intensity: 84.004 Position: 1494.09 Intensity: 86.270 Position: 1516.63 Intensity: 90.178 Position: 1591.57 Intensity: 90.210 Position: 1621.51 Intensity: 89.353 Position: 1675.84 Intensity: 88.746 Position: 3009.20 Intensity: 90.569

Nuclear Magnetic Resonance (NMR) Data: NMR data were obtained on a Bruker AM-300 FT NMR spectrometer. Tetramethylsilane (TMS, 0.03%) was used as an internal standard and CDC, as the solvent. There is a trace amount of HO and 1-propanol as impurities in the H NMR sample. MIN. INTENSITY-4.678 INTENS. LEVEL- 4.678 Fl- 2851.34 Hz- 9.5002 PPM MAXY-23.50000 NOISE 0.07379 F2- 1950.89 Hz-6.5001 PPM PP CONSTANT 1.00000 SENS. LEVEL 0.29518 CURSORFREQUENCY 7552 7574 1577 PPM 8.3988 8.3715 8.3683 8.3520 8.3487 8.3453 8.3380 8.0263 8.0187 8.0124 79944 7.9424 7.8874 7.6889 7.6647 7.6629 7.4961 7.4810 7.4781 7.4753 7.4650 7.4620 7.4518 7.4494 7.4452 7.4294 7.3786 7.3750 7.3542 7.3302 7.2412 7.2375 6.9760 6.9207 INTENSITY 25.719 18.583 19.228 2520.748 2512.559 2511.597 2506.729 2505.710 2504.709 2502.522 2408.972 2406.680 2404.779 2399.395 2383.793 2367.281 2307.682 2300.428 2299.882 2249.837 2245.307 2244.413 2243.585 2240.483 2239.605 2236.540 2235.816 2234.539 2229.810 2214.578 2213.475 2207.226 2200.023 2173.320 2172.223 2093.732 2077.143 1593 15.256 13.851 20.072 16.515 13.643 18.390 22.432 15.841 17.549 23.666 28.484 29.035 7.056 38.418 51.396 42.601 37.255 7602 7856 7862 7868 7882 10 13 7970 8132 15 8153 8301 8306 8317 8325 8327 8331 23 51.643 57.108 46.286 26 27 8385 8368 12.045 10.049 13.917 4.906 24.908 10.034 18.018 15.940 8497 32 8713 8759 34

sa 03 007 goo. -0 35 096 25 8 8 ら 96 59 66 24 ョ02629 00 59 P 73 3-6770 2 25226 266 S0STSH。.RAANT F D - ccc.FHP0046 0 0000726 3-069884. 302427 090 .. 0S00-.,.3 20 30 35 222 62 29 3566 133 T 4

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