Week 2: The Winners Please!

My comments in red.

1) “Oxidation of Cinnamyl Alcohol using Pyridinium Chlorochromate” 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. Looks good! Has a column chromatography step. Why cinnamyl alcohol? Does it matter?
2) “Vanillin Synthesis from 4-Hydroxybenzaldehyde.” Douglass F. Taber, Shweta Patel, Travis M. Hambleton, and Emma E. Winkel, J. Chem. Educ. 2007, 84, 1158.Two-step synthesis experiment. Uses bromine and sodium ethoxide – potentially nasty stuff. Has a column chromatography step
3) “Preparation of Banana Oil (Isoamyl Acetate)” (any number of lab manuals and websites) A Classic! I did this one as an undergrad. We were excited to find a microwave version of the experiment. However, we were quickly disappointed to find it needed rather specialized equipment.
4) “Identification of a Conjugated Diene from Eucalyptus Oil” 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. The Diels-Alder Reaction of a Conjugated Diene in Eucalyptus Oil. Very intriguing – the text does not even give away which will be the major diene in eucalyptus oil.
5) “Synthesis and Recrystallization of Adipic Acid” 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. I like the Doxsee & Hutchuson Green Chemistry book. They have a nice companion website that gives advice and discusses each experiment. http://greenchem.uoregon.edu/gems.html
6) Using a Premade Grignard Reagent to Synthesize Tertiary Alcohols in a Convenient Investigative Organic Laboratory Experiment,” Michael A. G. Berg and Roy D. Pointer. J. Chem. Educ. 2007, 84, 483. My first Grignard in long time. Wish us luck!
7) 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. I’ve had this one in my “idea” file for awhile. A challenging experiment. Hopefully we can sort this out. Potentially expensive. I ordered a dozen new chemicals for this one.

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