Each of you should choose an experiment from Pavia or one of your choice from the literature that involves a project you'd like to work on. You may not choose the same experiment as another student in the class. Some suggested experiments are given below. Precisely follow the instructions in Pavia or the literature for your first attempt and then change two of the variables (temperature, solvent, order of addition, related reagent, related catalyst, etc.) one at a time, and see how each change affects the outcome. Some experiments may also be converted from obtaining qualitative results to obtaining quantitative results (Experiment 18 is an example). If you choose the isolation of an essential oil, you will need to analyze the structure of the active ingredient with at least FT-IR, FT-NMR and GC.
Each project should include as part of the research an analysis of the starting material and product, if you are doing a synthesis, or an analysis of the active ingredient, if you are analyzing an essential oil, using one of the available molecular modeling programs. Include in the report an analysis of the HOMO and LUMOs involved in the reaction and an estimation of the relative energies (steric and heats of formation) of the starting material and product(s).
The initial preparation for this experiment will be a literature search to find the initial paper for the experiment you wish to run. The details are given in the experiment schedule. Read Technique 20: Guide to the Chemical Literature, (pp. 760-771 in Pavia) before you begin your search. If you are taking Chemical Literature, check with Dr. Whitling if you want to base your final paper on the experiment you plan to do.
Experiment Pages in
Pavia 18: Reactivities of Alkyl
Halides 190-193 25: Methyl Stearate from Methyl
Oleate 244-248 26: Phase-Transfer Catalysis:
Addition of Dichlorocarbene to Cyclohexene 248-255 37: Enamine Reactions:
2-Acetylcyclohexanone 323-333 38:
1,4-Diphenyl-1,3-butadiene 333-338 39: Relative Reactivities of
Several Aromatic Compounds 338-342 40: Nitration of Methyl
Benzoate 342-346 41: Benzocaine 346-352 45:
N,N-Diethyl-m-toluamide: The Insect Repellent
"OFF" 366-378 48: The Diels-Alder Reaction of
Cyclopentadiene with Maleic Anhydride 402-410 57: Isolation and Identification of
the Active Ingredient in an Essential Oil - Analysis of
Lavender, Oregano, Basil, Thyme, Sage, Dill,
Tarragon, or Rosemary 487-491 58: Friedel-Crafts
Acylation 493-499 61: Michael and Aldol Condensation
Reactions 504-507
You can also choose to analyze a favorite flavor or fragrance and then attempt to synthesize one or more of the components. One fragrance that has always intrigued me is the aroma of French fries. A quick search through the web did not yield an answer. Other flavors or fragrances may also come to mind. Some possibilities are given above. If you choose one of the herbs in bold face early enough, I may be able to harvest the fresh herb and freeze it until you need it.