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Spring Semester 2009:
Our first experiment of the semester was our attempt to contribute to the Open Notebook Science "Solubility Challenge." Determining the solubility of an organic compound in an organic solvent is not an awfully advanced experiment, but the education value of the endeaver was enhanced by having student design their own procedure based on the ONS solubility challenge guidelines. Some student results were contributed to the ONS Solubility Challenge wiki.
Our second experiment was the Diels Alder Reaction between Anthracene and Maleic Anhydride. This is a classic Organic Chemistry reaction. Many references to this procedure can be found on the internet, We were adapting the basic procedure from "Experiments in Organic Chemistry" 2nd edition (2000) by R.K. Hill & J. Barbaro.
Our third experiment was the ever popular Steam Distillation of Essential Oils
We distilled cloves, anise, oregano, fennel, and cumin to collect and analyse the extracted essential oils.
This is a very basic experiment that is found in several Sophomore Organic Chemistry Laboratory Manuals.
Fourth on the schedule was the "Combinatorial Synthesis of Azo Dyes" lab that we had done last Spring.
This year we tried a new electrophilic naphthalene derivative (1,5-dihydroxynaphthalene) to react with the azo compounds.
Our fifth lab was the "Oxidation of Secondary Alcohols to Ketones with Household Bleach (NaOCl)."
We had done a variation of this experiment with isoborneol in previous years.
This year we studied the oxidation of 2, 3, and 4-methyl-1-cyclohexanols.
An additional week was added to the oxidation experiment where we tried to improve the previous week's experiment or evaluate and alternative way to oxidize alcohols such as the "Solvent-free Oxidation of Secondary Alcohols to Ketones with Potassium Permanganate/Copper Sulfate"
Our sixth experiment was a variation of last year's Synthesis of a Tertiary Alcohol Using a Pre-Made Grignard Reagent, but this year we used 2, 3, and 4-methyl-1-cyclohexanone instead of benzophenone.
It was very interesting to compare the relative ratios of the two diastereomeric products formed (cis and trans-methyl-1-phenyl-1-cyclohexanol).
The next experiment of the semester was a two-week effort to produce Ethanol from Various Starch Sources.The main sources were frozen sweet corn, frozen potatoes, and minute rice.
We performed the Synthesis of Aromatic Esters experiment again this year. We synthesized two esters from last year: propyl 2-methylbenzoate, and propyl 4-methylbenzoate. We also made four newe esters: isopropyl 2-methylbenzoate, isopropyl 4-methylbenzoate, propyl gallate, and isopropyl gallate.
We ended the semester with the Synthesis of Luminol, an experiment adapted from Experiment 48: Luminol, in Pavia, Lampman and Kriz, “Introduction to Organic Laboratory Techniques: A Contemporary Approach” (1976) Saunders.
Fall Semester Labs:
At Dominican University we do a four-week first semester introductory sequence.
All four labs together lead to the separation and identification of a mixuture of two unknowns.
2008 Labs from Dominican University
Kinetic Invesitigation of Substitution
Chromatography Theory Worksheet
Dehydration of Methylcyclohexanols
2007 Labs from Dominican University
Post an experiment and/or discussion! invite key = ochemrules
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Spring Semester Labs:
We distilled cloves, anise, caraway, cinnamon, and cumin to collect and analyse the extracted essential oils.
This is a very basic experiment that is found in several Sophomore Organic Chemistry Laboratory Manuals.
#2a "Oxidation of Cinnamyl Alcohol using Pyridinium Chlorochromate" was developed by a group of four students from: Experiment #14 in Mohrig, J. R. “Modern projects and experiments in organic chemistry: Miniscale and standard taper microscale.” (2003) New York; Basingstoke: W.H. Freeman; Palgrave Macmillan.
#2b "Synthesis of a Tertiary Alcohol Using a Pre-Made Grignard Reagent" was adapted by a group of four students from a recent JCE article: Michael A. G. Berg and Roy D. Pointer. J. Chem. Educ. 2007, 84, 483.
#3 "Identification of a Conjugated Diene from Eucalyptus Oil” was adapted by a group of 4 students from: Lehman, J. W., Lehman, J. W., Operational organic chemistry, & 3rd. (2004). Microscale operational organic chemistry : A problem-solving approach to the laboratory course. Upper Saddle River, N.J: Pearson Prentice Hall. This was an interesting find, I thought. I have done a couple of different Diels Alder experiments over the years: maleic anhydride and cyclopentadiene, as well as maleic anhydride and anthracene.
#4 “Synthesis and Recrystallization of Adipic Acid” was adapted by a group of 4 students from: Experiment 5, Doxsee, K. M., & Hutchison, J. E. (2004). Green organic chemistry : Strategies, tools, and laboratory experiments Southbank, Vic., Australia ; United States: Thomson-Brooks/Cole
#5 "Combinatorial Synthesis of Azo Dyes" was adapted from: A Combinatorial Experiment Suitable for Undergraduate Laboratories Benjamin W. Gung and Richard T. Taylor in the Journal of Chemical Education, Vol 81, No. 11, November 2004 and Daniel R. Palleros,Experimental Organic Chemistry, John Wiley & Sons, Inc., 2000, pp. 627-628.
Its a variation of the classic "Synthesis of Methyl Orange" that I performed as an undergraduate.
#6 Synthesis of Isopentyl Acetate (Banana Oil) was developed by a team of students from a website: “Preparation of Banana Oil” . Many websites and lab manuals have versions of this very same experiment. I performed this experiment in 1979 from Pavia D. L.; Lampman G. M.; Kriz G. S. “Introduction to Organic Laboratory Techniques: a contemporary approach” 1st edition 1976 W. B. Saunders Company.
#7 “Synthesis of Chemiluminescent Esters” was developed by a team of students from a recent JCE article: “Synthesis of Chemiluminescent Esters: A Combinatorial Synthesis Experiment for Organic Chemistry Students,” Duarte, Robert; Nielsen, Janne T.; Dragojlovic, Veljko. J. Chem. Educ. 2004, 81, 1010. A good resource for this experiment is a website: “Chemiluminescence of Oxalate Esters”
#9 “Vanillin Synthesis from 4-Hydroxybenzaldehyde” This lab was developed by a team of students from a recent JCE article: “Vanillin Synthesis from 4-Hydroxybenzaldehyde.” Douglass F. Taber, Shweta Patel, Travis M. Hambleton, and Emma E. Winkel, J. Chem. Educ. 2007, 84, 1158. An online version of the lab was available at the Douglass Taber website; University of Delaware.
We are looking for schools to join us in a collaborative project studying the:
#10 “Synthesis of Aromatic Esters"This lab was developed from a recent JCE article: Wade P.A.; Rutkowsky S.A.; King D.B. A simple combinatorial experiment based on Fischer esterification - An experiment suitable for the first-semester organic chemistry lab. J Chemical Education 2006, 83(6), 927-928. This, of course, is a version of the ever-popular “banana-oil” lab found in a multitude of laboratory manuals such as: Pavia D. L.; Lampman G. M.; Kriz G. S. “Introduction to Organic Laboratory Techniques: a contemporary approach” 1st edition 1976 W. B. Saunders Company.
#11 "Ugi Synthesis Collaborative Project" This experiment represents the beginning of collaboration with the UsefulChem Bradley open notebook science group of graduate and undergraduate research at Drexel University. The goal of the UsefulChem project is to use the Ugi 4 component reaction to synthesize possible anti-malarial compounds. Open notebook science allows immediate dissemination of experimental results that invites advice and suggestions as well as complementary experiments that enhance and advance the project. We are going to reproduce some of the Drexel results as well as perform three complementary reactions that have not been done at Drexel.
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