Dr.Glaser�s �Chemistry in the News� HMO* style To Accompany Wade, Organic Chemistry,4/e.Chapter 6 Alkyl halides: NucleophilicSubstitution and Elimination Chapter 7 Structure and Synthesis of Alkenes Chapter 8 Reactions of Alkenes Chapter 2.11-2.13 Intermolecular Bonding
WE”LL STICK AT NOTHING, March 25, 1999The Article from DuPont
Editorial Chapter 6
Do you know what some may argue is the most important discovery for themodern plastics industry? You may be surprised to find it in yourkitchencabinets! Roy J. Plunkett was certainly surprised inthe 1930s when heaccidentally invented what is now known as Teflon. Infact, manyhouseholds today take their non-stick cookware for granted. Little dothey know that Teflon, which gives cookware it”s non-stick property, isa polymer composed of tetrafluoroethylene (C2F4)monomers. As discussed in this article, Teflon also aids in keeping materialssterile. By replacing ethene”s hydrogens with fluorine atoms, thechemical attains a slippery quality that prevents bacteria from bindingto it. Since molecules connect by sharing or exchanging electrons, itreasons that fluorine, the most electronegative element, resistsinteractions with other molecules. The fluorine”s large size shieldsthe interior carbons, preventing them from reacting-thus nothing sticksto Teflon.Teflon”s lack of chemical reactivity lends it to literally endless possible uses. It is a well-known registeredtrademark of theDupont Corporation, which has promotedtheirproduct in a variety offoreign and domestic markets. One interesting use in the field ofchemical science is the production of bottles for storage of thereagents used in trace analysis. Teflon, as well as improvements indetection, allows impurities to be detected at the sup-ppb level.While some claim there are hidden environmental dangers of Teflon andits fumes, we simply recommend not keeping your pet parakeetin thekitchen. Teflon has become a household expression used far beyond thebounds of non-stick cookware and its chemical properties-even used topoke fun at the Prime Minister of England.
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Question 1: What is the formula and organization of the monomer unit of Teflon?Answer 1: the monomer unit of Teflon is Tetrafluoroethylene, which is C2F4. The Carbons are SP2 hybridized, and share a double bond. Two fluorine atoms are bonded to each carbon, and the geometry around the carbon atoms is trigonal planar. Question 2: How might the monomer unit of Teflon be synthesized? Give a detailed mechanism for the synthesis.Answer 2: To synthesize the monomer unit of Teflon, tetrafluoroethylene, we need to start with ethynyl halide, (XC2H).
First we reduce the triple bond with fluorines to give us (HXC2F2), or difluoro-halo-ethylene. After that we reduce the double bond once again witth fluorines, giving us (HXC2F4), tetrafluoro-halo-ethane. The last step is to eliminate the HX. This restores the carbon to carbon double bond and gives us our final product, (C2F4), tetrafluoroethylene. Question 3: A major benefit to these new super-slippery polymers is improved hygiene. What are some reasons this new way of keeping things sterile might be better than the old way of heat sterilization by autoclaves? Are there any reasons that the old way might be better?Answer 3: There are many answers to this question. We could bring up that heat sterilization must be done over and over in contrast to the polymer which must only be applied once. Heat sterilization takes time and energy, but has been proven to work. Also, just because bacteria cannot stick to these new slippery polymers on a chemical level, does that imply that on a larger scale the polymer coated object will always be sterile? This new method of sterility certainly needs a little lab experience before it”s considered trustworthy. Question 4: How are the intermolecular Van der Waal”s forces affected when we replace the hydrogens in ethane with fluorines to make the monomer unit of Teflon? Also, why are the Van der Waal”s forces affected at all?Answer 4: The Van der Waal”s forces are almost completely eradicated between the Teflon molecule and outside molecules. This is because when we replace the hydrogens with fluorines, the Teflon molecule as a whole becomes very inert. The fluorine atoms prevent the temporary dipole moments necessary for the Va der Waal”s forces to exist. Question 5: How might the use of these new super-slippery halogen saturated polymers eventually affect the environment? What might be some of the dangers associated with these new polymers?Answer 5: This question is the open-ended philosophical/social/political question. There are many acceptable responses as long as some thought is put into them. =) cheerio.