Esterification Test Lab Report

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This experiment set out to identify the structural properties of an unknown alcohol (unknown A). In our case, Unknown A. In order to achieve this goal an esterification reaction was used to bind the unknown alcohol to an anhydride ester carbonyl containing three fluorine’s on both alpha carbons, named trifluoroacetatic anhydride. After obtaining the crude product an IR was taken to ensure the presence of the ester. At this point, it was acknowledged that our crude product did contain an ester, based upon peaks shown in the IR (A C-O bond at 1105.01 PPM of intensity 148.063). In order to further characterize our product, and understand what structure our unknown alcohol had contributed to it, we observed the boiling point through use of a Hickman…show more content…
Throughout the process we were able to eliminate unlikely candidates and narrow our focus down to a very specific possibilities. The refractive index of our alcohol was observed to be approximately 1.3339. This value allowed us to narrow our options to Isobutanol (1.3389), 2-butanol (1.3339), and Tert-butyl alcohol (1.3628). The boiling point of our product was observed to be 95 degrees Celsius. Given room for misjudgment, we again narrowed our selection process down to Isobutanol (BP of 95 degrees Celsius), 2-butanol (BP of 93 degrees Celsius), and Tert-butyl alcohol (BP of 90 degrees Celsius) . Using a provided CNMR we concluded that there are six total carbons present in the compound and contained chemical shifts that are indicative of two primary carbons (9.4 and 19.0, the later being shifted up more due to proximity to the ester), a secondary carbon (28.5), a tertiary carbon (76.7), a single bonded carbon with three halide attachments (117), and carbon apart of an ester group (158). Also, using a provided HNMR of our unknown alcohol, we identified the carbon at 5.0256 ppm to be our tertiary carbon alpha to the ester, while the carbon at 1.6780 ppm is our secondary carbon beta to the ester. Finally, two primary carbons were identified, one at 1.3438 being beta to the ester, and one at 0.9354 being gamma to the ester. The CNMR and HNMR provided strong evidence that support the

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