Below are the results of an H-NMR run on a crude product of N,N\'-(o-phenylene)b

Question

Below are the results of an H-NMR run on a crude product of N,N'-(o-phenylene)bis(p-toluenesulfonamide) and the general reaction for which the formation follows. Also included is the amounts of the chemicals used in the reaction. Two mols of p-toluenesulfonyl chloride are required for every one mol of o-phenylenediamine. The crude product was made with only 1.13 mols of p-toluenesulfonyl chloride, making p-toluenesulfonyl chloride the limiting agent and leaving an excess of o-phenylenediamine. After the twenty four hours of mixing required to complete the reaction had past, the product was evaporated, extracted with water and ethyl acetate, dried with anhydrous MgSO4, then evaporated once more.

Label each of the peaks shown on the H-NMR spectrum.

1g o-phenylenediamine, 2g p-toluenesulfonyl chloride, 10mL pyridine, 20mL water, 20mL ethyl acetate. Deuterated DMSO was used as a solvent for the H-NMR.

25568838142731617502751065105503 295 15555533398888866666655433333933 66666666666666666666432 9898655 :3 1 7 9 8 6 4 3 7 6 442199097754 CD 12 11 10 9 8 7 6 5 4 3 2 1 ppm CJ 068923 434386 441121 0 0

Explanation / Answer

2.353 s 3H x 2 CH3 of toluene methyls

7.311 - 7.353 m 1H x 4 CH of aromatic p-tolyl two protons of adjascent to methyl group

7.558 - 7.595 m 1H  x 4 CH of aromatic p-tolyl two protons of adjascent to sulfonyl group

6.345 - 5.400 m 1H adjascent to amino proton

6.836 - 6.892 m 1H adjascent to amino proton

6.591 - 6.671 m 2H two protons meta to the amino group

6.974 s for two amino protons.

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