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Lab 5 Discssion

Lab 5 Discssion - The bromination of acetanilide yielded...

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The bromination of acetanilide, yielded 4-bromoacetanilide as the major product. The observed melting point range was 149-168°C, which was slightly below the literature value of 165-168°C. ( cite) state error. The appearance of the purified crystals matched the literature description of light beige, nearly white, crystalline solids. The percent yield from this experiment was 61%, a substantial yield. the 1 H NMR of the bromination product, showed 4 groups of chemically inequivalent hydrogens. There were two unique groups of hydrogens attached to the benzene ring had a doublet peak at 7.569 ppm. These peaks signify symmetry in terms of the aromatic substituents, and thus it could be inferred that the product was para because ortho and meta products would display six distinct peaks. The set of hydrogens closest to the bromine had a doublet peak of 7.471ppm while carbon next to the carbonyl group had a singlet at 2.056ppm. The bromines electronegativity was responsible for the downfield shift of these two hydrogens.
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