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UT CH 302 - Polymers and Biopolymers
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Lecture 22: Polymers and Biopolymers In the previous lecture we learned that by using carbon as the primary backbone, we can create a seemingly endless array of molecules built on covelent bonds to carbon. The simple concepts we learned at the beginning of the year about bonding—like structures being formed based on the number of valence electrons and the stability of filled shells, make it possible to rationalize why different structures are possible. We can even rationalize the reactivity that occurs by applying simple concepts like electronegativity or more sophisticated concepts in thermodynamics. What should be most impressive is just how many different kinds of even relatively small molecules (molecular weights of a few hundred) we can build using carbon backbones and attaching all manner of functional groups. In fact most of the compounds we take for granted in our daily lives, like vitamins, and medications, and molecules that make it possible to see color or to smell or to taste, are built on even the smallest variations in organic molecules. A few examples of theses are shown below, not because you are expected to learned them, but more just to say, wow, this might actually be pretty interesting and make learning organic worthwhile.Estrogen Vitamin C brilliant blue food coloring Polymers Now these small organic molecules are amazing given the their complexity and diversity of function, but they are not really what is really important about organic molecules. Actually it is the ability of small organic molecules to polymerize that makes life really interesting (and possible.) The rest of this lecture describes this process by which small organic molecule units are able to form molecules that have molecular weights of millions and larger. We will first look at the polymers built on very simple organic molecules that are responsible for the many products we use in our daily lives—like rubber or Plexiglass or Teflon. We will then look at biopolymers which are as they say, “the building blocks of life.” What I will want you to take away from this survey is a general appreciation for how these polymers are formed, and for the ones I lay out for you in the notes or the worksheets, the ability to identify what monomeric units are responsible for forming a specific polymer. Addition Polymers. We have learned that there are certain general classes of organic chemical reactions: substitutions, additions and eliminations. You can imagine that these can occur in such a way that a one or more small organic molecules can react to produce molecules of ever increasing size. For example, the polymerization of ethane to form polyethylene.Another famous example, that is done as a demo just about everywhere, including this class, is the production of nylon from adipic acid and hexamethylene diamine. In the sequence below the two starting materials form the monomer that polymerize to form nylon polymerizationA table of some common monomers, their polymer formulas and their famous names is shown in the table below. Common sense tells you that the actual commercial production of polymers is not only staggeringly complicated but also staggeringly lucrative. So please don’t leave this section thinking that heating up a couple of molecules to form a longer chain is all it takes to produce a product or that the simple formulas shown above are the actual structures of the products you buy. To achieve certain desirable properties, polymers are allowed to form in much more complicated ways, as seen in the picture below and in the example of rubber (polyisoprene below.)Biopolymers. This is not a biology class, or even a biochemistry class, but unless you have had your head in the sand most of your life, you already know that those folks define four basic categories of biopolymers. Biopolymers are similar to the polymers described above in that simple building blocks of monomeric units are used to create first, important classes of intermediately sized molecules, that are then linked to form the biopolymers that define what it means to be alive. If you learn nothing else in the material below, you should walk away knowing that • carboxylic acids combine with hydrocarbon groups to make fatty acids • sugars that make polysaccharides that make the carbohydrates starches and cellulose • amino acids that make polypeptides that make proteins • the bases and phosphates and sugars that make nucleosides and nucleotides that make the nuclei acids DNA and RNA I will briefly define each of these in terms of the simply units that form them and in terms of the important functions they have in our lives. What I want you to notice is that even those these are magnificently large, systematically defined structures, they are at root, a collect of bonds formed because an atom wanted to satisfy the octet rule, and the reactions that created these polymers were simple acid base or redox reactions based upon the thermodynamic and kinetic concepts that we have been learning. Fatty Acids. Fatty acids are the simplest of the biopolymers in that they can consist simply of a carboxylic acid functional group with a hydrocarbon chain. We can divide these into two categories. The saturated hydrocarbons that are made with alkane groups (no double bonds. ) These saturated fatty acids are the bad guys that do damage to your cardiovascular system, but fast food places love them because they don't go rancid. Butyric (butanoic acid): CH3(CH2)2COOH C4:0 Caproic (hexanoic acid): CH3(CH2)4COOH C6:0 Caprylic (octanoic acid): CH3(CH2)6COOH C8:0 Capric (decanoic acid): CH3(CH2)8COOH C10:0Lauric (dodecanoic acid): CH3(CH2)10COOH C12:0Myristic (tetradecanoic acid): CH3(CH2)12COOH C14:0Palmitic (hexadecanoic acid): CH3(CH2)14COOH C16:0Stearic (octadecanoic acid): CH3(CH2)16COOH C18:0Arachidic (eicosanoic acid): CH3(CH2)18COOH C20:0Behenic (docosanoic acid): CH3(CH2)20COOH C22:0The unsaturated hydrocarbons include at least one double bond. Myristoleic acid: CH3(CH2)3CH=CH(CH2)7COOH C14:1 Palmitoleic acid: CH3(CH2)5CH=CH(CH2)7COOH C16:1 Oleic acid: CH3(CH2)7CH=CH(CH2)7COOH C18:1 Linoleic acid: CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH C18:2 Alpha-linolenic acid: CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOH C18:3 Arachidonic acid CH3(CH2)4CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(CH2)3COOH C20:4 Eicosapentaenoic acid C20:5 Erucic acid:


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UT CH 302 - Polymers and Biopolymers

Type: Miscellaneous
Pages: 12
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