Experimental Chemistry II, CH 463 & 463H Poster Abstracts for 2006
Department of Chemistry – Oregon State University
June 8, 2006 1:30 – 3:30
Gilbert Addition 313
1-2006. QUANTITATIVE STUDY OF THE PHOTOREDUCTION OF 4-BROMO-4'-METHYLBENZOPHENONE TO A SUBSTITUTED BENZPINACOL. J.W. Torgerson, Department of Chemistry, Oregon State University, Corvallis, OR 97331
Solutions 4-bromo-4'methylbenzophenone were placed in a Rotating Rack Rayonet reactor at 350nm at intervals of 5, 15, 30 and 45 minutes and yielded a photoreduction quantum efficiency of 7.75%.
2-2006. SYNTHESIS AND QUANTITATIVE PHOTOREDUCTION STUDY OF 4-PHENYLBENZOPHENONE. S. Rector, Department of Chemistry, Oregon State University, Oregon 97333.
4-phenylbenzophenone was synthesized via a Friedel-Crafts acylation route from benzoyl chloride and biphenyl with a 25% yield. A subsequent FTIR study was completed to determine the photoreduction quantum efficiency of 4-phenylbenzophenone’s ability to dimerize to form 4, 4’diphenylbenzpinacol. This experiment gave a value of 2.36 mol reduced/mol photon.
3-2006. QUANTITATIVE ANALYSIS
OF THE PHOTOCHEMICAL REDUCTION OF
4-BROMO-4’-FLUOROBENZOPHENONE. P. Heflinger,
Department of Chemistry, Oregon State University, Corvallis, OR 97331
The photochemical reduction of 4-bromo-4’-fluorobenzophenone to the resulting substituted benzopinacol was studied. Four solutions were irradiated with UV light at 350 nm for 5, 10, 20, and 40 minutes. The samples were then studied via IR spectroscopy to with the overall goal of determining Phi (reduction).
4-2006. SYNTHESIS OF 4-CHLORO-4'-FLUOROBENZOPHENONE. Nicole D.A. Howell
Oregon State University, Corvallis, Oregon 97330.
4-chloro-4'-fluorobenzophenone was synthesized using a Friedel-Crafts acylation reaction, using 4-chlorobenzoyl chloride, fluorobenzene, and an AgCl3 catalyst. Vacuum distillation was used to obtain a yield of 67.41%. Once IR, NMR, melting point, and TLC data were found, these values were compared to literature values.
5-2006. 4-chloro-4'-iodobenzophenone - Does not play well with photons. Kyle Hanson, Oregon State University, Corvallis, Oregon 97331.
Benzophenones are well known for their phosphorescence, which has been studied at length at reduced temperature. In this experiment, an attempt was made to encase 4-chloro-4'-iodobenzophenone (CIBP) in polymethylmethacrylate, in order to study the phosphorescence at room temperature by isolating individual molecules. Success was found with some substituted benzophenones, although the iodine of CIBP breaks off under UV light, preventing effective polymerization.
6-2006. COMPARISON OF THE SYNTHESIS AND CHARACTERISTICS OF 4-METHYLBENZOPHENONE AND 4-METHYLBENZOPINACOL. Amanda J. Wilson; Department of Chemistry, Oregon State University, Corvallis, Oregon, 97331.
4-methylbenzophenone was synthesized using the Friedel–Crafts Acylation from benzoyl chloride, aluminum chloride, and toluene. A photoreduction of the 4-methylbenzophenone produced 4-methylbenzopinacol. The benzopinacol was produced after exposing a mixture of 4-methylbenzophenone, isopropanol, and glacial acetic acid catalyst to UV light. Characterization of each product was conducted in the form of: 1H–NMR, 13C–NMR and IR Spectroscopy. The results of this experiment showed a 70.56% yield of the benzophenone and a clear photoreduction of the benzopinacol.
7-2006. SYNTHESIS AND CHARACTERIZATION OF 4-CHLOROBENZOPHENONE AND THE CORRESPONDING PINACOL. David H. Burford, Department of Chemistry, Oregon State University, 97331
4-Chlorobenzophenone was synthesized via a Friedel-Craft acylation and characterized via infrared spectroscopy, melting point determination, HNMR and CNMR. The product was then subjected to UV light to form the pinacol 1,2-bis(4-chlorophenyl)-1,2-diphenylethane-1,2-diol. This was characterized by infrared spectroscopy, melting point determination and HNMR.
8-2006. SYNTHESIS AND CHARACTERIZATION OF 4-BROMOBENZOPHENONE. Beth M. Spree, Department of Chemistry, Oregon State University, Corvallis, OR 97322
4-bromobenzophenone was synthesized via the Friedel-Crafts
method using benzoyl chloride and an excess of bromobenzene. The product was
recovered with a 54.3% yield after vacuum distillation and recrystallization in
100% ethanol. Through various techniques such as TLC, H NMR, C NMR, IR, COSY,
and melting point determination, the identity of the product was confirmed to be
4-bromobenzophenone.
9-2006. ULTRAVIOLET REDUCTION EFFICIENCY OF BIS(4-METHOXY) METHANONE IN ISOPROPANOL
John V. Dollhausen, Department of Chemistry, Oregon State University, Corvallis OR 97331.
The photopinnacolization of a dilute solution of bis(4-methoxy) methanone in isopropanol is found to occur with a high quantum yield, but not two (in terms of benzophenone disappearance) as reported elsewhere. Aspects of the experimental setup and procedure which could account for the discrepancy with previously published results are discussed.
10-2006. SYNTHESIS OF 4-CHLORO-4'-METHYLBENZOPHENONE AND BENZOPINACOL FORMATION AND CHARACTERIZATION. Mollie R. Waller, Department of Chemistry, Oregon State University, Corvallis, OR 97331
4-Chloro-4'-methylbenzophenone was synthesized from toluene and 4-chlorobenzoyl chloride using Friedel-Crafts acylation. Following synthesis the benzophenone was converted to benzopinacol by exposure to UV. Formation of the benzopinacol in solution was confirmed by IR and in crystalline form by H NMR. The extent of the photochemical reaction was analyzed using IR and the photoreduction quantum efficiency of the benzophenone determined.
11-2006. Synthesis and Characterization of 4-bromo-4'-methoxybenzophenone. Preston Skaggs, Department of Chemistry, Oregon State University-Corvallis, OR 97330
This describes the synthesis and characterization of a rarely studied compound 4-bromo-4’-menthoxybenzophenone. A Friedel-Crafts type reaction was carried out by reacting 4-bromobenzoyl chloride and anisole on an ice bath with an aluminum chloride catalyst. The reaction produced a 46.3% yield. Characterization was done using 400 MHz NMR, Nicolet 5P FT-IR, and a melting point of 151°C.
12-2006 GETTING THE VIBE ON 4-IODOBENZOPHENONE - A STUDY OF PHOSPHORESCENCE. Kimberly M. DeMorrow, Department of Chemistry, Oregon State University, Corvallis Oregon 97331
Understanding the vibrational levels of 4-iodobenzophenone could help determine new applications for this compound. Phosphorescence of 4-iodobenzophenone (p-IBP) showing the life time and vibrational levels between the ground state and the excited states will be presented.
13-2006. SYNTHESIS AND PURIFICATION OF 4-BROMO-4'-PROPYLBENZOPHENONE. Kelly Dick, Department of Chemistry, Oregon State University-Corvallis, Oregon 97331
4-BROMO-4'-PROPYLBENZOPHENONE was synthesized via a Friedel-Craft Acylation from n-propylbenzene and 4-bromobenzoyl chloride using aluminum chloride as a catalyst. The experiment resulted in a 75% yield. The benzophenone was then purified, and the melting point, IR, H NMR, and C NMR spectra were obtained and compared to literature values.
14-2006 THE INFLUENCE OF FLUORINE ON THE NMR SPECTRA OF 4-FLUORO-4’-METHOXYBENZOPHENONE
Katherine M. Fordyce, Department of Chemistry, Oregon State University, Corvallis, Oregon 97331
A study concerning the influence of fluorine on the nuclear magnetic resonance (NMR) spectra of 4-fluoro-4’-methoxybenzophenone is presented here. Three types of NMR analyses were performed: 1HNMR, 13CNMR, and 9FNMR. Analysis of the spectra revealed the effect of the fluorine atom’s large coupling constant; atoms on the fluorine ring were split by the carbonyl group and the fluorine atom. As a result, all signals from the fluorine ring were split into doublets. In addition, two signals from the different benzene rings were superimposed. This overlap of different signals required additional analysis in order to determine the identity of the atoms causing the signals. Finally, the NMR analyses were used to confirm the identity of the experimental product as 4-fluoro-4’-methoxybenzophenone.
15-2006. Synthesis and Characterization of 4-Methoxy-4’-Methylbenzophenone. Tuan M. Nguyen,
Department of Chemistry, Oregon State University, Gilbert Addition 311, Corvallis, OR 97333
The synthesis of 4-methoxy-4’-methylbenzophenone was done via Friedel-Crafts acylation reaction of p-anisoyl chloride and toluene in the presence of AlCl3 as catalyst. The product was characterized through TLC, FT-IR, H1- NMR and melting point determination. Through the used of these techniques, the production of 4-methoxy-4’-methylbenzophenone was confirmed.
16-2006. THE SO-CALLED SYNTHESIS OF 4-METHOXY-4'-METHYLBENZOPHENONE. T. Graville, Department of Chemistry, Oregon State University, Corvallis, Oregon, 97330
In all aspects of chemistry there is a degree of uncertainty and element of surprise. Synthesizing 4-Methoxy-4'-Methyl-benzophenone demonstrated to be more of a challenge than predicted. This presentation shows what may have really happened and possible reasons why, along with lessons for future researchers.
17-2006. CHARACTERIZATION OF 4-FLUOROBENZOPINACOL AND DETERMINATION OF THE QUANTUM YIELD OF THE CORRESPONDING BENZOPHENONE. Abigail Joyce, Department of Chemistry, Oregon State University, Corvallis, OR 97331
Two different experiments were done on 4-fluorobenzophenone. One sample was ethanol (~10 ml) saturated with the 4-fluorobezophenone(~2 g) and was irradiated for 2 weeks with 250 nm light, until a solid-the benzopinacol, precipitated out which was then characterized (MP, NMR, IR) confirming production of desired benzopinacol. The second was a dilute concentration of the ketone (0.0505M) in methylcyclohexane. It was divided into 4 tubes and irradiated for 5, 10, 20, and 30 minutes. An IR was then taken of each sample and benzophenone concentrations then determined by calibration curve methods. The quantum yield was then determined to be 15%.
18-2006. SYNTHESIS AND CHARACTERIZATION OF 4,4’-DIMETHYLBENZOPHENONE. D.F. Crawford, Department of Chemistry, Oregon State University, Corvallis, OR 97331.
4,4’-dimethylbenzophenone was synthesized from p-toluoyl chloride and toluene via Friedel Crafts acylation. The reaction occurred with a percent yield of 43.70%. The product was characterized via melting point (92-93ºC), IR spectroscopy, and HNMR spectroscopy and compared to literature values.
19-2006.
THE QUANTITATIVE SYNTHESIS AND ANALYSIS OF
4-BROMO-4'-CHLOROBENZOPHENONE.
Melialani A.C.L. Stone, Department of Chemistry, Oregon State University,
Corvallis, OR 97331
The synthesis of 4-bromo-4’-chlorobenzophenone was conducted via Friedel-Crafts acylation using 4-chlorobenozyl chloride (acid chloride), bromobenzene (substrate) and aluminum chloride (catalyst) as starting materials. The final product was isolated via vacuum distillation and recrystallization. The final purified product was identified using NMR spectroscopy, IR spectroscopy, melting point characterization and physical characteristics, such as color and physical state
20-2006. Jeremy Gersztyn. Rescheduled.