Chemistry 337 Laboratory - References
The links below go to the on-line version of the reference, where possible. If it's not highlighed, it's not on-line. You may need to be on campus, or logged in to UVic for these to work properly.
Copies of textbook references cannot be posted, but should still be available in the Reserve Room of the Library. You should always consult your coursepack for any experiment.
|Experiment 1 - The Cis-Trans Equilibrium of N-Acetylproline
1. This experiment was adapted from Williams, K.R.; Adhyaru, B.; German, I., Alvarez, E. J. Chem. Ed. 2002, 79, 372–373.
2. It has been observed that in D2O, the signal for the alpha proton of the cis isomer is always downfield (higher delta value) of the a proton signal of the trans isomer, independent of the pH of the solvent.
|Experiment 2 - The Hammett Equation
1. Jaffe, H.H. Chem. Rev. 1953, 53, 191-261. This is the reference where the value of rho for the solvent was found. Don’t copy this one!
2. The σ and σ- constants presented here are compiled from several sources.
3. A text reference for the Hammett equation may be found in March, J. Advanced Organic Chemistry, 3rd edition, Wiley-Interscience, New York, 1985, chapter 9. Also see Clayden, J., Greeves, N., Warren, S., Wothers, P. Organic Chemistry Oxford University Press, Oxford, 2001, p 1090–1100.
|Experiment 3 - Nucleophilic and Enzymatic Catalysis
1. This rate constant is a sum of several rate constants; k0 = kH2O[H2O] + kOH-[OH-] + kH2PO4-[H2PO4-] + kHPO42-[HPO42-]. The individual contributions to k0 do not affect the results of this experiment.
2. The pKa for imidazole (protonated) is 7.1. The pKa’s for the side chains of the amino acids are as follows: histidine (protonated side chain) 6.0, cysteine 8.3, serine 13.6, aspartic acid 3.9. Data taken from Solomons, T.W.G. Organic Chemistry, 4th edition, J. Wiley and Sons, 1988.
3. This experiment is adapted from Head, M.B.; Mistry, K.S.; Ridings, B.J.; Parker, M.J.; Smith, C.A. J. Chem. Ed. 1995, 72, 184–186.
|Experiment 4 - The Effect of Cationic Micelles . .
1. Menger, F.M.; Portnoy, C.E. J. Am. Chem. Soc. 1967, 89, 4698–4703.
2. Bunton, C.A. Catal. Rev. Sci. Eng. 1979, 20, 1–56.
3. Romstead, L.S. in Micellization, Solubilization and Microemulsions, Volume 2, Mittal, K.E., Ed., Plenum Press, New York, New York, 1977, pp 509–530.
4. Al-Lohedan, H.; Bunton, C.A.; Romstead, L.S. J. Phys. Chem. 1981, 85, 2123–2129.
5. These values, plus a value for kM, were used in the literature to provide a close fit of equation 9 to the experimentally determined kP.6
6. Rodenas, E.; Vera, S. J. Chem. Ed. 1985, 62, 1120–1121.
|Experiment 5 - Catalysis: The pH-Rate Dependence of the Hydrolysis of Aspirin
1. Most textbooks on physical organic chemistry will have a section on catalysis. The major literature source for this experiment is: Edwards, L.J. Faraday Trans. 1950, 723–735. Please obtain this reference from the reserve reading room (or the on-line link). The original journal is getting very damaged, beyond the point of repair.
2. Marrs, P.S. J. Chem. Ed. 2004, 81, 870–871.
|Experiment 6 - Molecular Recognition
1. Pedersen, C.J. J. Am. Chem. Soc. 1967, 89, 7017–7036. See also the following page.
2. Pedersen shared the 1987 Nobel Prize in chemistry with Donald Cram of UCLA and Jean-Marie Lehn of Strasbourg. Pedersen published 5 papers on crown ethers: the full paper cited above, 3 notes and a review with Frensdorff.
3. The MSDS sheet for picric acid shows the material to be toxic, and an irritant. It is also known that dry picric acid (or its salts) can be an explosion hazard. The material you are given to work with is in dilute aqueous solution, thus eliminating the explosion hazard. Proper adherence to the disposal instructions above will guarantee that the material is disposed of in a safe manner.
4. The Handbook of Chemistry and Physics (55th edition) gives the dielectric constants of dichloromethane and chloroform as 9.80 and 4.80, respectively.
|This web page was last updated on July 21, 2011 by Peter Marrs.
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