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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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During the Bromine test, the bromine transformed from brown to clear indicating the presence of an alkene. Also during the permanganate test, the compound changed from purple to brown. This also indicates the presence of an alkene, which indicates the E2 reaction did occur. These two positive test allowed for a GC spectrum to be obtained, if the IR confirmed there was no water in the final compound. The IR spectrum obtained, did contain a peak at 3388 cm-1, indicating an alcohol group present, but the degree of the peak was so small that a GC spectrum could be obtained.

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Also indicative of the ester functional group are the wavelength peaks between 1250-1050cm-1, signaling the presence of -C-O- bonding. Additional peaks in the spectrum, such as the shaky broad peak

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The last TLC indicated there were compounds present, which

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The bromine test yielded a positive result; each brown drop of the bromine reagent added disappeared in the solution. The positive result indicates the presence of an alkene. The IR spectrum collected corresponds greatly to the sample spectrum of cyclohexene. The peak at 3023.01indicates a sp2 C-H group, the peaks at 2924.79 and 2859.53 indicates a sp3 C-H, and the peak at 1653.31 indicates a carbon-carbon double bond. Furthermore, the absence of a peak at 3322.01 shows that there is not an alcohol group in the product, meaning that the product did not contain any

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Other expected peaks at 1583.02 cm-1 (aromatic C-C) and 1016.21 cm-1 (C-O alcohol) are also seen and there are no outlying peaks that would suggest other products as well. From the 1H NMR spectra for 2-nitrophenol, a very similar result is observed. We see multiple peaks in the 8.0-6.5 PPM region suggesting the aromatic ring and the correct 8.2 (d, 0.80 H), 7.6 (dd, 0.78 H), and 7.1 (m, 2.00 H) peaks for the ortho substituted product. We also see a very strong outlying peak at 10.6 (s, 0.87 H) representing the alcohol hydrogen in the nitrophenol along with no other strong outlying peaks except for the 2.1 PPM acetone peak.

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