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This has three basic sections: 1.Addition Polymerisation 2.Condensation Polymerisation 3.Uses of polymers
This kind of polymerisation is typified by the presence of a carbon – carbon double bond in the monomer. A monomer is a small molecule that makes up a polymer. HH C HH C
H H high pressure/trace O2 CC catalyst HH ethene
In addition polymerisation: • The polymer is the only product • Involves the opening out of a double bond • The conditions of the reaction can alter the properties of the polymer You do not need to know the mechanism of addition polymerisation, but it exists mainly by a free radical mechanism. Oxygen is often used to generate a radical that can then proceed to polymerise the alkene. The board specifies than you know the following polymerisation reaction:
H CC H
HHHH CCCC H H
Polymerisation of poly(phenylethene). Otherwise known as polystyrene. You are expected to be able to do the following things with addition polymers: 1.Predict the repeating unit of the polymer given the monomer 2.Predict the monomer from the polymer – displayed formula and even empirical formula. 3.Know about stereochemistry of addition polymers.
1. H CC H CH3 H propene H 2.infront. Cl Cl Cl HHHHHH HC HC HC CC HH CC HH CC HH Cl Cl Cl Cl Page 2 . draw 2 repeating units and name the polymer formed. For each of these. CC HH Cl H CH3H CH3 H CH3 CC CC CC CH3H Cl Cl Cl Cl CH3H CH3H 4. Also put a ring around the repeating unit. H C H C CH3 O C O CH3 methyl-2-methylpropenoate Predicting the monomer from the polymer This is kind of the opposite to what you have just done. the empirical and the molecular formula. but they may ask you to draw different formulae. write the full structural formula. H C H C H Cl HHHH CC C C H Cl H Cl poly(chloroethene) aka polyvinylchloride (pvc) chloroethene Notice the name of the polymer is the name of the monomer in brackets with the word poly. Try these. F C C F FF tetrafluoroethene 4. This is easy.Predicting the repeating unit. in each case. H CC H 3. H CC HH 3. Cl Cl H Cl H Cl CC HH Cl 2. basically open out the double bond. 1.
Stereoisomerism in Addition polymers. Generally used to make plastic bottles. called LDPE or low density poly(ethane). HDPE has a much higher boiling point due to these more ordered regions. Isotactic. Isotactic. All the methyl groups are on the same side. H CHH CHH CHH CHH CHH CHH CHH CH 33333333 This has an impact on the properties of the polymer. Poly(propene) and stereoisomerism. syndiotactic and atactic. 1. This is a completely random allocation of methyl groups along the carbon skeleton. The less random. using an aluminium/tin catalyst at 50°C and 1. This is a very regular type of polymer chain. H H H H H H Atactic. 2. H H H H H H H This varying degree of randomness will affect the strength and melting point of the polymer. the stronger the polymer and the higher the melting point 3 . Until two chaps called Ziegler and Natta came along in the early 1950s. The chains formed a tangled mass. A slightly less regular but still very ordered polymer. Ziegler and Natta also discovered that they could make stereo regular polymers. Syndiotactic. the quality of polymer that could be obtained was variable. They discovered a method of controlling the polymerisation process very accurately. By using this new catalysis method they could control the process and produce HDPE this has a much stiffer structure due to areas of crytallinity where the polymer chains are much more ordered.5atm. Previous to this only one type of poly(ethene) could be made. H 3. The methyl groups alternate the side of chain they are on.
2-diyl benzene-1. Polyesters The OCR example here is terylene. Condensation polymers A condensation polymer generally involves 2 monomers that have different functional groups. O C O the ester linkage O n HO C O C OH + n HO CH2 CH2 OH heat with an acid catalyst O C O C O CH2 CH2 O n poly(ethan-1.because the chains can get closer together which impacts on the interactions between the polymer chains. and possibly predict either what the monomers might be or the polymer.4-dicarboxylic acid and ethane-1.2-diol. The ester linkage is based around the reaction between an acid and an alcohol to form an ester + water.4-dicarboxylate) You need to be able to reproduce this. a polymer of benzene-1. Common condensation polymers include polyesters (the ester linkage) and polyamides (the amide linkage as in proteins). More ordered side chains = stronger van der Waals. Page 4 . Monomer A + Monomer B Polymer + small molecule (normally water). Hence the term condensation polymer. They also involve the elimination of water or another small molecule.
silk) O CN H the amide linkage In 1935 Wallace Carothers (who had just discovered polyesters). They also specify Kevlar. OCR specify nylon as a need to know polyamide.6-diaminohexane (CH2)6 N H H O C HO (CH2)4 C O OH hexanedioic acid O N H (CH2)6 NC (CH2)4 C O H part of a nylon polymer chain The 6. the first 6 comes from the number of C atoms in the amine monomer.Polyamides These involve the linkage of two monomers through the amide linkage as in proteins (e. A polyamide is essentially the same as a polyester except one the molecule containing the alcohol functional group contains a primary amine. O H2N NH2 HO C (CH2)4 C OH O O N H NC H part of the kevlar polymer chain (CH2)4 O C Page 5 .6 comes from the number of Carbon atoms in the monomers.6 from a diamine and a dicarboxylic acid. They produced a polymer called nylon 6. the second comes from the acid. turned their attention to polyamides.g. H N H 1.