Sunday, July 26, 2015

Trifluoroacetate Esters



In this experiment, the unknown alcohol (5) was reacted with trifluoroacetic anhydride for form a trifluoroacetate ester and trifluoroacetic acid. Alcohol 5 was 2-pentanol, which underwent a nucleophilic substitution reaction of exothermic esterification to form 2-pentyl trifluoroacetate and trifluoroacetic acid, which has a pKa of -0.25. The alcohol was determined to be 2-pentanol because the trifluoroacetate ester product had a boiling point of 112 deg.C and a refractive index value of 1.3453. The literature provided had a boiling point of 120 deg.c and a refractive index value of 1.3456. Because the boiling point can vary more due to ranging and contamination, the determination was based more upon the refractive index value with coordination to the boiling point. The actual product mass was 0.713 g, and the theoretical yield was 1.0075 g (3.88 x 10 -3 mol). This resulted in a percent yield of 70.8%. The deduction of percent yield accumulated through the steps of the reaction. Product could have been lost in the 2 extractions of aqueous layers, the transfer of the organic layer to the test tube for drying, and the transfer of the organic layer to a 3.0 mL vial for weighing.
Conclusion:
In this lab, an esterification reaction of unknown alcohol #5 and trifluoroacetic anhydride was successfully run in order to form 2-pentyl trifluoroacetate and trifluoroacetic acid. The unknown alcohol was determined by the refractive index value of the ester—1.3453—and the boiling point—112 deg.c. The 2-pentyl trifluoroacetate had a percent yield of 70.8% due to multiple extractions and transferring the product.

1 comment:

  1. Corticotropin-releasing factor (CRF) is a 41-amino acid peptide derived from a 196-amino acid preprohormone. CRH belongs to corticotropin-releasing factor family and is secreted by the paraventricular nucleus (PVN) of the hypothalamus in response to stress. Ovine CRF produces a longer lasting ACTH response in humans than human CRF, CRF Trifluoroacetate

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