1.11 How to get hooked on chemistry
10 Questions
How I got Hooked on Chemistry
 
A long time ago I took a course at the University of Connecticut called Advanced Organic Chemistry. Our Professor was Sam Huang, who gave us instructions on the first day and then we rarely saw him again. We were told we had to complete three experiments:
  1. Identify an unknown pure chemical sample
  2. Purify and identify 2 unknown chemicals in a mixture
  3. Create a new chemical
He gave each of us a vial with a liquid or a powder in it. We had three weeks to identify it. Mine contained a shiny white solid. Under a magnifying glass it appeared as flat white plates. It melted sharply at 212 degrees Celsius. A big clue was discovered when I placed it under ultraviolet light- it glowed with a bright blue color. With this information, and by converting it to a few derivatives, I was able to correctly identify the solid as Anthracene, a constituent of coal:(1)

                                                                                   
                                                                                          anthracene
   
Next, he gave each of us another vial. We were told it was a mixture of two chemicals. We again had three weeks to separate and identify them. This time the vial had a dull white powder in  it. I watched as my lab partners set up complex chromatography and distillation devices and began tedious separations of their mixtures. Ugh. Under a magnifying glass two distinct crystals could be identified- needles and plates. It took a couple days, but I was able to separate my mixture using a pair of tweezers and the magnifying glass, and identify each sample. A few of my classmates accused me of cheating.

Finally, we had the rest of the semester to make a new chemical. I got so excited about this one that I skipped spring break and spent it at the library. Yes, I had become a science nerd, big time. It was my first time reading real accounts of chemical research and I found it fascinating. Here people were creating chemicals to treat cancer, make bulletproof plastics, all sorts of projects …but what really interested me was the field of natural products- the study of natural, not man-made, chemicals. I found a research paper where the individual chemical that creates the main flavor of pineapples and strawberries was recreated in the lab. It was called furaneol, (2) and I decided I would make my own version of it with a slight chemical change designed to give it a sweeter taste. 

                                                                      
                                                                              furaneol

The initial experiments were a disaster. There were chemicals I needed that weren't in the stockroom. My lab partners were goofing off while I was working with dangerous chemicals. And soon the deadline was approaching, but in the end I managed to make a small amount of a white solid, and the spectroscopic data matched the chemical structure. I realized that with enough effort virtually any substance one could imagine could eventually be made, and it seemed to me this was a powerful tool. I changed my major from biology to chemistry, and two years later I had my first job making chemicals designed to study cancer. (3)

In this class each of you will be given a similar opportunity to explore, imagine, and create using the chemical skills and knowledge from this class.  By the time this class is near complete you will be ready to identify unknown samples and safely perform your own initial chemical research in a field of your choice. 

References:
1. The unique fluorescence of anthracene has been used as a tool for extraterrestrial life. See for example:A Search for Interstellar Anthracene Toward the Perseus Anomalous Microwave Emission Region. Iglesias-Groth, S., et al Monthly Notices of the Astronomical Society, volume 409, issue 2, page 880, 2010. Available online at http://arxiv.org/pdf/1005.4388v1.pdf  .
Anthracene has also one of three substances used in the "holy smoke" in a papal conclave: Vatican Reveals Recipes for Conclave Smoke, by Henry Fountain, 
New York Times, March 12, 2013, available online at http://www.nytimes.com/2013/03/13/science/vatican-reveals-recipes-for-conclave-smoke.html?smid=pl-share

2. Furaneol has been synthesized many times from simpler substances. See for example: Syntheses of 2,5-Dimethyl-4-hydroxy-2,5-dimethyl-4-hydroxy-2,3-dihydrofuran-3-one (furaneol), a Flavor Principle of Pineapple and Strawberry. Buchi,G., Demole, E., and Thomas, A. Journal of Organic Chemistry, volume 38, number 1, pages123-125, 1973. Available online at http://pubs.acs.org/doi/abs/10.1021/jo00941a025.

 

3. One of the controversial methods used to study cancer is to create large quantities of cancer-causing substances and to determine exactly what happens when living things are exposed to them- this is known as carcinogenesis. See for example: A Study of Chemical Carcinogenesis. Synthesis and Mutagenecity of Dihdrodiol Metabolites of Benzo[b]fluoranthene. Amin, S., Hussain, N., Brielmann, H., Hecht, S. Journal of Organic Chemistry, volume 49, number 6, pages 1091-1095, 1984. Available online at http://pubs.acs.org/doi/abs/10.1021/jo00180a026


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