Dr. Glaser's "Chemistry is in the News"
To Accompany Bruice, Organic Chemistry, 3/e.
Chapter 2. An Introduction to Organic Compounds. Nomenclature, Physical Properties, and Representation of Structure.

Editorial Comments

Get your favorite web browser up, do a search for "Prince William Sound" and you will find sites describing the region of PWS. Prince William Sound, a largely unspoiled wilderness of steep fjords and mountains, glaciers and rain forest, rests calmly at the head of the Gulf of Alaska. Sheltered by the Chugach Mountains in the north and east, and the Kenai Peninsula in the west, and with its sparkling blue waters populated by copious numbers of whales, porpoise, sea otters and seals, the Sound has a relatively low-key tourist industry. The only significant settlement, spectacular Valdez, at the end of the trans-Alaska oil pipeline, and Cordova, a modest and untouristy fishing community, are the respective bases from which to see the Columbia and Childs glaciers. Just behind the Chugach peaks, lies the vast and relatively untramped world of Wrangell-St Elias National Park. The very definition of paradise, if you'd ask me. --- That was then, and this is now: Today, the Prince William Sound is on the public's mind as the site of one of the greatest oils spill in history, the Exxon Valdez accident in 1989. Read all about it and its aftermath at the website of the "Exxon Valdez Oil Spill Trustee Council.".

One reads about such "oil spills" all the time. There are hundreds every year. As I am writing these comments, there is a big tanker breaking apart just off the coast of Florida. CNN is there to satisfy everybody's appetite for destruction. We hear mostly about the ones that happen close to populated areas like the one in Tokyo Bay. There you have Tokyo, Kawasaki and Yokohama, three of the largest cities of Japan all within reach of the fumes of the oil spill.

Of course, these accidents are sad and the damage is great. But getting bitter and opposed to technology is not an option. Considering the magnitude of the enterprise and its benefits to society, the oil business is actually quite safe. Think about it. Still, some accidents do happen and more should be done to act fast and with a comprehensive strategy such that damage is minimized at all cost. This is an area where many improvements can be made and one should ask for these improvements to be implemented without delay. The fastest way toward assuring more efficient clean-up is by way of public pressure and that means education of the public is the first step. Since the eduction of the public is the finest goal of public education, let us start right now, appropriately, with the study of an article in the Journal of Chemical Education.

A recent article in the Journal of Chemical Education was entitled "Oil Spill Remediation Using Magnetic Particles: An Experiment in Environmental Technology." You can find the article in your library, using the full citation: J. D. Orbell, L. Godhino, S. W. Bigger, T. M. Nguyen, and L. N. Negh J. Chem. Educ. 1997, 74, 1446. But then again, this is the cyber-age: We are all connected! So all we need is a hyperlink to read the abstract of the article online. How convenient! Still interested after reading the abstract? If you have acrobat reader installed and if you or your school have an account with JCE, you may download the J. Chem. Educ. article as a pdf file (choose Full Text when the choice appears). Once you have the pdf file displayed on your screen, you can go ahead and print yourself a hardcopy that looks just like a photocopy of the "real" article (I mean the one printed in the traditional sense).

Questions

Question 1: We all talk about "oil". Do you know what major chemicals actually are contained in the black, unrefined crude oil?

Answer 1: Oil is a very complicated mixture that contains usually 85 - 90 % carbon, 10 - 14 % hydrogen, 0 - 1.5 % oxygen, 0.1 - 3 % sulfur, 0.1 - 0.5 % nitrogen, and traces of many elements. Three classes of hydrocarbons are the main constituents of oil and these are alkanes, cycloalkanes (in the petroleum field also known as naphthenes), and aromatic compounds. The alkanes are the major fraction and they include the straight chain alkanes from methane all the way up to C₃₀H₆₂ and even up to C₉₀H₁₈₂. Among the cycloalkanes, the dominant ones are cyclopentane, cyclohexane, and cycloheptane.

Question 2: Briefly describe the polarities of crude oil (e.g. consider octane) and of water.

Answer 2: Water is a polar liquid and water molecules are held together by strong hydrogen bonds. Octane is a nonpolar compound and the intermolecular forces are weak and of the van-der-Waals type.

Question 3: Briefly explain why crude oil and water do not mix. For simplicity, you may discuss the solubility of octane in water.

Answer 3: The solution of octane in water is endergonic. While the octane solution in water has a mixing enthalpy that is very close to zero, the mixing does not occur because of the entropy term! This phenomenon is called the "hydrophobic effect" and it has many important biological implications.

Question 4: The oil spill remediation technique described in the JCE article uses polethylene (PE) or polyvinylchloride (PVC) coated pellets. Preview chapter 26 on "Synthetic Polymers" to learn about the chemicals PE and PVC. Considering the polarities of these polymers, explain why they are used.

Answer 4: The polymers are nonpolar and it is for this reason that the crude oil will be absorbed on the coated pellets.

Chemistry & Society.
Question 5: This question is meant to start a discussion. Perhaps you can discuss this question with your peers (i.e. on the course discussion list). Here is the question: Consider the relative advantages and the disadvantages of an oil based economy and a nuclear energy based economy.