Experimental Chemistry II, CH 463 & 463H Poster Abstracts for 2008
Department of Chemistry Oregon State University
Wednesday, June 4, 2008 1:30 3:30
Gilbert Addition 313
1-2008. SYNTHESIS AND CHARACTERIZATION OF A REVERSATROL ANALOG, 3,4,4-TRIMETHOXYBENZOPHEONE. Wong, Jeff, Department of Chemistry, Oregon State University-Corvallis, OR 97330
The reversatrol analog, 3,4,4-trimethoxybenzophenone was synthesized using an organometallic nucleophile with an addition to an aldehyde, followed by an oxidation step. The properties measured include TLC, 1H/13C NMR, IR spectroscopy, melting point, and mass spectrometry.
2-2008. SYNTHESIS AND PHOTOREACTIVITY OF 3, 4-DIMETHOXYBENZOPHENONE. Jeffrey B. Eitner, Department of Chemistry, Oregon State University, Corvallis, Oregon 97331.
The compound 3, 4-dimethoxybenzophenone was synthesized from a Grignard reaction using phenylmagnesiumbromide and veratraldehyde. Standards were made from dilutions of A stock solution of the benzophenone in isopropanol. Four samples of the stock solution were exposed to intense UV light in a photoreactor for variable amounts of time. The samples and standards where run on the FTIR. The resulting data was used to calculate the photoreactivity of the benzophenone. 3, 4-dimethoxybenzophenone was found to have limited or no photoreactivity.
3-2008. MEAN GREEN SYNTHESIS OF 4-METHOXYBENZOPHENONE. Nicole A. Kurhanewicz, Department of Chemistry, Oregon State University, Corvallis, Oregon, 97331
An attempt was made to synthesize the compound 4-methoxybenzophenone via Friedel-Crafts acylation of anisole with benzoic acid. A solvent-free variation of Friedel-Crafts was applied using tosic acid on graphite powder as a catalyst.
4-2008. THE PHOTOREDUCTION OF 4-FLUORBENZOPHENONE TO 1,2-(4-FLUOROPHENYL)-1,2-(PHENYL)ETHANEDIOL Katherine A. Scriven, Oregon State University, Department of Chemistry, Corvallis, Oregon 97331
Synthesized 4-fluorbenzophenone was photoreduced in isopropyl alcohol at a UV wavelength of 254nm to form 1,2-(4-fluorphenyl)-1,2-phenylethanediol. Conformation of this formation was characterized through melting point, FTIR, NMR, and geometric optimization using HyperChem analysis.
5-2008. SYNTHESIS OF 3,4-DIMETHOXY-4'-METHYLBENZOPHENONE USING GRIGNARD ADDITION. Eric J. Titus, Department of Chemistry, Oregon State University-Corvallis, Oregon 97331.
In this report, the synthesis of 3,4-dimethoxy-4'-methylbenzophenone is outlined using a Grignard addition followed by a manganese dioxide oxidation as an alternative to performing a Friedel-Crafts synthesis to synthesize substituted benzophenone. The product of this reaction was confirmed using its melting point, GCMS, and both 1-dimensional and 2-dimensional NMR techniques (1H, 13C, COSY, HSQC, HMBC).
6-2008. SYNTHESIS AND CHARACTERIZATION OF 4-ETHYL-4'-METHOXYBENZOPHENONE IN COMPARISON TO CHARACTERIZATION OF 4-CHLORO-4'-ETHYLBENZOPHENONE. George Ganio, Department of Chemistry, Oregon State University, Corvallis, OR 97331.
The synthesis of 4-ethyl-4'-methoxybenzophenone was attempted using ethylbenzene and 4-methoxybennzoyl chloride with AlCl3 as the catalyst via Friedel-Crafts acylation method. Characterizations of the final purified product included IR, 1H-NMR, 13C-NMR and melting point. Since the final product was not completely synthesized, 4-chloro-4'-ethylbenzophenone was also characterized in order to show the similarities between the benzophenones. An additional 2D-NMR was ran for further characterization of 4-chloro-4'-ethylbenzophenone.
7-2008. SYNTHESIS AND CHARACTERIZATION OF 4-METHOXYBENZOPHENONE. Addison A. Rutter, Department of Chemistry, Oregon State University, Corvallis 97333
4-methoxybenzophenone has been synthesized via a Friedel-Crafts Acylation. Benzoyl chloride and anisole were combined in a nitrogen environment and reacted in the presence of heat and an aluminum chloride catalyst. After quenching the reaction and removing the aqueous layer, the product was condensed using a rotovap and steam distillation and treated with base before recystalizing twice in ethanol. The final percent yield was 48.73%. Its melting point was found to be 60.5-62°C. Additionally, the results from analysis by infrared spectroscopy, mass spectrometry, HNMR and 13CNMR corresponded with literature values, indicating a high level of purity.
8-2008. SYNTHESIS AND CHARACTERIZATION OF 4-CHLORO-4-FLUOROBENZOPHENONE. D.M. Welch, Department of Chemistry, Oregon State University-Corvallis, Oregon 97330.
The synthesis of 4-chloro-4-fluorobenzophenone was achieved via Friedel-Crafts Acylation of 4-chlorobenzoyl chloride with fluorobenzene and an aluminum chloride catalyst. The percent yield of this reaction was 40.6%, yielding 10.26 g. The synthesized 4-chloro-4-fluorobenzophenone was characterized by comparing the melting point to a literature value, using FTIR to identify major functional groups, and using 1D and 2D NMR to confirm the structural configuration.
9-2008. UV ABSORPTION, EMISSION, AND EXCITATION OF 4-BROMO-4'-FLUOROBENZOPHENONE IN METHYLCYCLOHEXANE AND ETHANOL. LIA DIBIASE Department of Chemistry, Oregon State University-Corvallis, Oregon 97330.
The electronic transitions of 4-bromo-4-fluorobenzophenone were tested in a non-polar solvent, methylcyclohexane, and a protic polar solvent, ethanol. The first experiment tested the absorption of the compound in each solvent. The second experiment tested the excitation and emission in the concentrated solutions with both solvents. The absorption experiment yielded the transition data for the S0-S1, S0-S2, and S0-S3 transitions of 4-bromo-4-fluorobenzophenone. The emission and excitation experiment helped determine the transition parameters for the T1 -S0 transition. Both experiments showed oscillator strength values that were higher for the compound in methylcyclohexane showing that transitions between the different energy levels were more favorable in the non-polar solvent.
10-2008. ABSORBANCE SPECTROSCOPY OF 4-METHOXY-4'-NITROBENZOPHENONE AND THE EFFECT OF SOLVENT DIPOLE AND DIELECTRIC ON TRANSITION STRENGTH AND TYPE. J.J.Kelley, Oregon State University, Department of Chemistry 97331.
A solvent study was conducted to compare the UV
absorbance spectrum of 4-methoxy-4-nitrobenzophenone in methylcyclohexane,
ethanol, and acetonitrile. The strongest observed transition in all three
solvents was an aromatic (π, π *) transition. No (n, π*) transitions were
observed at room temperature or at 77K. Overall, the polar solvent reveals the
(π, π *) transition of the carbonyl whereas non-polar and acetonitrile reveals
the (π, π *) transition of the nitro group. Lastly, plots of transition
oscillator strength (f) versus solvent dielectric (ε) and transition distance
versus solvent dipole were found to be linear.
11-2008. CHARACTERIZATION AND PHOTOCHEMICAL REDUCTION OF 4-METHYLBENZOPHENONE, David Ohm, Gilbert Addition 309, Chemistry Department, Oregon State University
The synthesis of this benzophenone using the Friedel-Crafts method produced a final yield of 39.8 %. Using NMR analysis gave the desired carbon and proton peaks typically found in 4-methylbenzophenone. The photoreduction of this benzophenone to its corresponding benzopinacol obtained a photoreduction quantum efficiency of 31.1% mol benzophenone / hv absorbed.
12-2008 SYNTHESIS AND CHARACTERIZATION OF 4-BROMO-4'-N-PROPYLBENZOPHENONE. NICOLE C. BAKER, 825 NW 23rd St. #46, Corvallis, OR, 97330.
4-bromo-4-n-propylbenzophenone was synthesized with a Friedel-Crafts Acylation from 0.11 moles of n-propylbenzene and 0.14 moles of 4-bromobenzoyl chloride combined in 65 mL of CS2 with the slow addition of AlCl3 as the reaction catalyst and was heated to completion (determined by TLC). After isolation a sharp melting point at 92.5 ± 1.0°C supported product purity which was reinforced by the clarity of the spectra used in characterization. Characterization was conducted by IR, MS, and specifically NMR analyses, confirming the intended product.
13-2008. SYNTHESIS OF 4-IODO -4'-METHYLBENZOPHENONE. Mariko Nonogaki, Department ofChemistry, Oregon State University, Corvallis, Oregon 97331.
The 4-iodo-4-methylbenzophenone is a compound which is sensitive to light and heat due to the large and heavy substituent of iodine, and there have been only a few reports concerning the compound. In this research, the synthesis of 4-iodo-4-methybenzophenone by Friedel Crafts acylation reaction was investigated using Perrier procedure. The obtained crystals were characterized by melting point, mass spectrum, IR, and NMR in order to confirm the purity of the product. The data showed the high purity, although the % yield from this synthesis was 5.50 %.
14-2008 SYNTHESIS AND SPECTROSCOPIC CHARACTERIZATION OF 4-BROMO-4'-METHYLBENZOPHENONE. T.M. Tokich, Department of Chemistry, Oregon State University, Corvallis, OR 97331.
4-bromo-4-methylbenzophenone was synthesized via the Friedel-Crafts method with toluene and 4-bromobenzoyl chloride. It was recovered with a 48% yield after recrystallization in ethanol. The product was characterized through IR, 1H-NMR, 13C-NMR and melting point. Further characterization of the product was determined though 2D NMR using COSY, HSQC, and HMBC.
15-2008. SYNTHESIS AND CHARACTERIZATION OF 4-BROMOBENZOPHENONE. Amber G. Robinson, Department of Chemistry, Oregon State University, Corvallis, OR 97331
The synthesis for 4-bromobenzophenone was developed and carried out via a Friedel-Crafts acylation using bromobenzene and benzoyl chloride. The final product was then characterized using IR, NMR, MS, and melting point.
16-2008. SYNTHESIS AND CHARACTERIZATION OF 4-CHLORO-4'-METHOXYBENZOPHENONE. Caitlin P. Phillips; Department of Chemistry, Oregon State University, Corvallis 97331.
4-chloro-4-methoxybenzophenone was synthesized via the Friedel-Crafts method with anisole and 4-chlorobenzoyl chloride. It was recovered with a 65% yield after recrystallization in isopropyl alcohol. The product was characterized using IR, CNMR, HNMR, and melting point. These techniques provided sufficient data to conclude that the product was both pure and the correct desired benzophenone. Additional photochemical experiments were then run on the pure product.
17-2008. SYNTHESIS OF 4-FLUORO-4'-METHYLBENZOPHENONE BY FRIEDEL-CRAFTS REACTION. Alaina L. VanHorn; Oregon State University, 97333.
4-fluoro-4'-methylbenzophenone was synthesized using 4-toluoyl chloride and fluorobenzene in carbon disulfide with aluminum trichloride as the catalyst in a Friedel-Crafts reaction. The product was tested using tlc and melting point to determine that the reaction was done, then 1HNMR was run to determine that the final product of the reaction was the intended intended product. 2DNMR was run to further characterize the product, as well as IR and mass spectrometry, both of which helped to prove that the final product of the reaction was the correct conformation, 4-fluoro-4'-methylbenzophenone. The final yield was 31%.
18-2008. SYNTHESIS OF 4-CHLORO-4'ETHOXYBENZOPHENONE. Kelly L. McDonald, Department of Chemistry, Oregon State University, Corvallis, OR 97331.
4-chloro-4'ethoxybenzophone was synthesized via Friedel-Crafts acylation using ethoxybenzene and 4-chlorobenzoyl chloride. Complications were encountered and "product" was observed before appropriate steps were conducted to complete the synthesis. It was determined that the alleged product was chlorobenzoic acid, an undesirable side product. After appropriate treatment to neutralize the solution, vacuum distillation, and recrystallization from ethanol, the desired product was obtained. Yield was determined to be 25%. IR NMR, and GC/MS spectra will be presented to demonstrate evidence of formation of the benzophenone.
19-2008. SYNTHESIS OF 4-CHLOROBENZOPHENONE. Sam Brady, Department of Chemistry, Oregon State University, Corvallis, OR 97331.
The 4-chlorobenzophenone was prepared using the Friedel Crafts acylation method using benzoylchloride, chlorobenzene as starting materials and aluminum chloride as a catalyst. The procedure generated a mixture of two isomers, 4-chlorobenzophenone and 2-chlorobenzophenone. The isomers were separated via an ethanol-water recrystalization procedure. Identification of the separated material was confirmed by IR spectroscopy, mass spectroscopy, H-NMR, and C13-NMR.
20-2008. NUCLEAR MAGNETIC RESONCE ANALYSIS OF 4-BROMO-4-CHLOROBENZOPHENONE. Noah Cannoy, Department of Chemistry, Oregon State University, 97331.
Why bother with the NMR of
4-bromo-4-chlorobenzophenone? Because my efforts to find any NMR of it in the
literature were less than fruitful. It was found to be necessary to use C NMR,
HNMR and all 2D experiments (COSY, HSQC, and HMBC) to interpret the severely
overlapped protons on the ring containing bromine which appeared as a false
singlet. The resolved doublets are on the ring with Cl are obvious. These
assignments are supported by empirical chemical shift calculations (ppm) showing
hydrogens #5 and #4 to be only 0.08 ppm apart.
Yates, Ripley R.