the microscale laboratory
in a collaborative manner as a function of the structure of the substrate and the reaction conditions. Although students recognize that precious metals catalyze hydrogenation reactions, here the absence of hydrogen encourages them to think about other avenues. Finally, in this experiment, students may confront the analysis of a product mixture containing some unconverted starting material. The complete quantitative analysis of spectral and chromatographic data is a significant and rewarding ~hallenge.~ Acknowledgment
Fund, and the National Science Foundation. It is under copyright by CURI and will be published with a group of experiments. We also warmly thank our students in Chemistry 25 and 26 for their interest, excitement, and comments. Literature Cited 1. Ricd, R. W.: Ditrler, M.A. J. Cham. Educ. 1991,68,22%231. R i d , R. W; Ditzler. M. A,; Jarref, R.: MeMaster, P.; Herrick, R. J Chem. Edue 1994. 71, W 0 5 . s ,N ~O* . ", J. R.; pinke, R. G. ~ ~ i ~ ~ ~ ~ ~ 2. couman. J. ~ , ~ e d e g u s.: dOrsonotrnnsition M e t d Chemistry: Universiv Science B o o k Mill Valley. CA. 1987. pp 768-775 and references therein. 1991,287 3. Dennis, M. W: Kolattukudy. P EEA~hiiiiifBimhhm~Lry~ndBiiPhy~iii CZi. 268
This experiment has been developed for a project sponsored by the College-University Resource Institute, Inc. (CURI) at seven colleges with support from the Camille and Henry Dreyfus Foundation, the Jessie Ball duPont 6Many extensons of I n s experiment are p o s s l b l e O L ~S t J O e n t S h a v e suggesteo examining t h e convers on of cn fa1a l a e n y o e s , d a o e n y d e s , and t h e s o m e r i c h a o , cyano, m e t n o x y , a n o t r ~ l l u o r o m e t n y l benzaldehydes
A30
Journal of Chemical Education
4. ~ s u j i ohno, . no, K.Srnrhpsis 1969, 157. 5. Tadano, K;ldogaki,Y; Tamada. H.:Susmi, T. J . Org Chem. lS87.52.1201-1210. 6. Tsuji, J. in "Organic Synthesis %a Metal Carbonyls", Wender, I.: Pino, P,Eds.; W3ey-lnterscie~e, 1977: Vol. 2. p 595. 7. Hawthorn, J. 0.; Wilt, M. H J O g . Chem. 1980,25,221&2216.Tsuji, J.;Ohno, K J. Amer Chem. Soc 1968,90,9449. 8. Ohno,K.;Tsuji. J. J A m w Chem. Soc. 1868.90.99-107. 9. Baldwin, J.E.;Barden, T C.: Pugh, R. L.; Widdison, W C. J. Ow. Cham. 1987.52, 3303.3307 Doughty. D. H.: MeGuiggsn, M. F:Wang, H.; Fignolet, L. H. Fundam. Re$. Homwmeous Cotol. 1919, 3, 909. Doughty. D. H.; Fignolet. L. H. J. A n r C h . Soc 1978,100.7083-7085. Abu-Haaanayn. F ;Goldmen, M. E.; Goldman, A. S. J. Amec Chpm. Sm. 1991,114,2520-2624. 10. Williamson, K L. Macroscale ondMicroseoie OgonieEqxrimmls: D.C. Heeth and Co: Lexington, MA. 1989.
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