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Friedel-Crafts Alkylations Lab Report

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The Characteristics of Freidel-Crafts reactions in the synthesis of bexarotene Lily C. Draga March 12 2023 Miami University Abstract The purpose of this experiment was to learn about Friedel-Crafts alkylations, acylations, and to perform the second step in the synthesis of bexarotene. The final, purified product had a percent yield of 22.44% and a Rfvalue of .69 which matched the provided standard. Peaks in the IR spectrum like the peak at 3018 cm-1 and another peak at 1384 cm-1represented groups known to be on the desired product. It can be drawn from this research that product 3 (1,1,4,4,6-Pentamethyl-1,2,3,4-tetrahydronaphthalene) was successfully synthesized from this reaction. Introduction The purpose of this experiment was to learn about Friedel-Crafts alkylations, acylations, and perform the second step in the synthesis of bexarotene. Friedel-Crafts reactions are used to create carbon-carbon bonds to aromatic …show more content…

Relevant peaks of the 13C NMR spectrum of the product and their assignment. The peak at 32 represented the 4 sp3 methyl groups in sections 2 and 3. The peak at 35.3 corresponded to equivalent carbon 4 and 7 which were sp3 c-c bonds. The peak around 34 corresponds with carbons 5 and 6. The peaks at 126, 134, 141, and 144 all correspond to the different aromatic carbons, and the peak around 21 ppm represents the ethyl group at point 1 coming off of the ring. Discussion The desired product that was aimed to be synthesized in this reaction was successfully synthesized. This is supported by multiple peaks from the IR spectrum. Peak 3018 represents the aromatic benzene and another peak at 1384 represents the Sp3 carbon-carbon bonds. It is also supported by 13C NMR and 1H NMR data. The purification of the synthesized product was successful as well. This is supported by the final TLC plate synthesized after the product was purified. (Image 2). Image 2. The TLC plate comparing the standard (left) and purified compound (right), with

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