ࡱ> q`  bjbjqPqP -::wrffffNNNNL,Pn QSSSSbsdtd<$hx` Qfbbff ffSS\ u u ufl f8SS uf u uwwSQ гեqNrpw|Lr0w؄vs؄ww؄x#e"Ee u]eqe#e#e#e t#e#e#effff%\>\>4ffffff 1.7 Introductory organic chemistry 1.7.1a Homologous series These have The same functional group Similar chemical properties The same general formula Gradually changing physical properties E.g. Alkenes: Functional group: double bond General formula: CnH2n Ethene C2H4 CH2=CH2 bp=-162oC, decolourises bromine Propene CH3CH=CH2 bp= -48oC, decolourises bromine But-1-ene CH3CH2CH=CH2 bp=-6oC, decolourises bromine Pent-1-ene CH3CH2CH2CH=CH2 bp=30oC, decolourises bromine Hex-1-ene CH3CH2CH2CH2CH=CH2 bp=64oC, decolourises bromine Important homologous series each with its own functional group include: Alkanes C-C, Alkenes C=C, Halogenoalkanes -Br, Alcohols -OH, Carboxylic acids -COOH, Ketones -C=O, Aldehydes -CHO, Amines NH2, and Nitriles C=N. Task 1.7.1(a)(i) Write molecular formulae for other alkenes. Task 1.7.1(a)(ii) Make and draw a model compounds for the formula C4H8 and the first two members of the homologous series for alkenes. Task 1.7.1(a)(iii) Draw structural formulae and write a general formula for alcohols and bromoalkanes. 1.7.1b Nomenclature The root name depends on the number of carbon atoms in the longest chain and any functional group. Numbers are given to the carbon atoms so that the lowest numbers are given to functional groups. Branch names are also included in the full name of an organic compound. no. of C atoms12345root namemethethpropbutpentbranch namemethylethylpropylbutylpentylformulaCH3C2H5C3H7C4H9C5H116 hex, 7hept, 8 oct, 9 non, 10 dec. The names of the functional groups are added at the end. Alkanes, -ane; Alkenes, -ene, Alcohols, -anol; Carboxylic acids, -anoic acid; Ketones, -anone; Nitriles -anenitrile and Aldehydes, -anal; Some names are added as prefixes e.g. Halogenoalkanes, chloro-, bromo- or iodo-; Amines, amino- Task 1.7b.1 name the first 10 alkanes and alkenes and some halogenoalkanes. The dash - separates numbers and words. 2-methylpentane not 4-methyl pentane CH3CH(CH3)CH2CH2CH3 (structural formula) CH3 | CH3CHCH2CH2CH3 (displayed structural formula) A fully displayed structural formula shows all atoms and all bonds. Skeletal formulae show bonds to C atoms as lines but leave out C and H atoms. E.g. ethene C2H4 \ / = / \ 3,4-dimethylhexane CH3CH3 | | CH3CH2CHCHCH2CH3 propan-2-ol CH3 CH (OH) CH3 When there are 2 or more functional groups in the same molecule and there is conflict over which suffix to use, we put them in alphabetical order: CH2Cl-CH2Br is 1-bromo-2-chloroethane Examples of naming organic molecules: But-1-ene CH3= CH CH2 CH2 Chloroethane CH3CH2Cl 1,2-Dibromopropane CH3CH(Br)CH2Br numbers are separated by commas Task 1.7.1b.2 Draw structural formulae for propane; 2-methylpropane; 2,2-dimethylbutane; 3-ethyl-2,5-dimethylheptane; 3-ethyl-2,4-dimethylpentane; 2,3,4-trimethylheptane; 3-ethyl-2-methylheptane. Task 1.7.1b.3 Draw structural formulae for but-2-ene; propan-1-ol; propan-2-ol; tribromomethane; 2-chloro-3,3-dimethylpentane. 1.7.1c Hazard and risk A hazardous substance can cause harm. How it is used leads to different levels of risk. Typical hazards include: Ethanol is flammable, chlorine is toxic, potassium manganate (VII) is an oxidizing agent, sulfuric acid is corrosive, plutonium is radioactive. Risk is always relative but is never zero. Task 1.7.1c.1 Classify the level of risk as high or low for (a) heating ethanol with a Bunsen flame or an electrical heater, (b) using chlorine in a open laboratory or in a fume cupboard, (c) pouring sulfuric acid wearing rubber gloves or with bare hands to improve grip, (d) handling plutonium behind window glass or leaded glass. 1.7.1d Risk assessment Risk reduction can be achieved by preparing risk assessments in which the hazard and the methods to reduce risk is noted. These may rely on general laboratory precautions such as the use of safety glasses, bans on eating and drinking. More specific measures such as using small amounts of a substance may help. The concentration of a poisonous substance and the length of time exposed to it are important in deciding risk. Routes into the body may be considered. A substance may be inhaled, ingested or absorbed through the skin. Less hazardous reactions can be used e.g. NaOH + HCl instead of sodium + HCl to make salt. Task 1.7.1d.1 Suggest how to reduce risk if a substance may be inhaled, ingested or absorbed through the skin. Task 1.7.1d.2 For a selection of different organic substances use hazcards to make a risk assessment for an experiment in which you have to heat the substance. 1.7.2 Alkanes 1.7.2a Alkane general formula The alkane general formula is CnH2n+2 The first is methane CH4, H | H-C-H | H Note C has only single bonds. Known as saturated. Task 1.7.2a Write molecular formulae, draw fully displayed structural formulae and make models for the next 4 alkanes; ethane, propane, butane and pentane. 1.7.2b Structural isomers of alkanes Structural isomers are compounds with the same molecular formula but different structural formulae. The atoms are arranged in a different order. e.g. CH3CH2CH2CH3 (butane) and CH3CHCH3 (2-methylpropane) | CH3 Task 1.7.2b Name, write molecular formulae, draw structural formulae and make models for the all of the structural isomers of butane, pentane and hexane. 1.7.2c Alkanes sources and uses Alkanes are separated from crude oil by fractional distillation  INCLUDEPICTURE "http://www.energyinst.org.uk/education/coryton/images/column.gif" \* MERGEFORMATINET  Task1.7.2c.1 Draw an alkane found in (a) liquefied petroleum gas, (b) petrol and kerosene, (c) in diesel. Most uses for alkanes involve burning them. With propane (C3H8), you can balance the carbons and hydrogens as you write the equation down. Your first draft would be:  INCLUDEPICTURE "http://www.chemguide.co.uk/organicprops/alkanes/padding.gif" \* MERGEFORMATINET  INCLUDEPICTURE "http://www.chemguide.co.uk/organicprops/alkanes/c3h8-1.gif" \* MERGEFORMATINET  Counting the oxygens leads directly to the final version:  INCLUDEPICTURE "http://www.chemguide.co.uk/organicprops/alkanes/padding.gif" \* MERGEFORMATINET  INCLUDEPICTURE "http://www.chemguide.co.uk/organicprops/alkanes/c3h8-2.gif" \* MERGEFORMATINET  With butane (C4H10), you can again balance the carbons and hydrogens as you write the equation down.  INCLUDEPICTURE "http://www.chemguide.co.uk/organicprops/alkanes/padding.gif" \* MERGEFORMATINET  INCLUDEPICTURE "http://www.chemguide.co.uk/organicprops/alkanes/c4h10-1.gif" \* MERGEFORMATINET  Counting the oxygens leads to a slight problem - with 13 on the right-hand side. The simple trick is to allow yourself to have "six-and-a-half" O2 molecules on the left.  INCLUDEPICTURE "http://www.chemguide.co.uk/organicprops/alkanes/padding.gif" \* MERGEFORMATINET  INCLUDEPICTURE "http://www.chemguide.co.uk/organicprops/alkanes/c4h10-2.gif" \* MERGEFORMATINET  If that offends you, double everything:  INCLUDEPICTURE "http://www.chemguide.co.uk/organicprops/alkanes/padding.gif" \* MERGEFORMATINET  INCLUDEPICTURE "http://www.chemguide.co.uk/organicprops/alkanes/c4h10-3.gif" \* MERGEFORMATINET  Task 1.7.2c.2 Write balanced equations for the combustion of methane, ethane and pentane. Cracking breaks less valuable large alkane molecules into more valuable smaller ones. The products include some alkenes which have double bonds. These can be turned into polymers. Cracking is a form of thermal decomposition. A lot of longer molecules produced from fractional distillation are cracked into smaller ones because there's more demand for products like petrol and Kerosine than for diesel oil. The products include compounds with double bonds such as ethene. C-C-C-C-C-C-C-C-C-C- --cracking---> C=C + C-C-C-C-C-C-C-C decane ethene octane big molecules small molecules alkanes mostly alkenes single bonds double bonds saturated unsaturated only good for fuels can be made into polymers  INCLUDEPICTURE "http://www.chemguide.co.uk/organicprops/alkanes/crackmodel.gif" \* MERGEFORMATINET  Industrial conditions for cracking vaporised hydrocarbons are to use a powdered catalyst at about 400C to 700C. The catalyst could be Aluminium oxide. Task 1.7.2c.3 Draw structures to show the hydrogen atoms in all of the compounds in the cracking reaction above. Draw structures to show molecules in other cracking reactions. Reforming is a process in which straight chain alkane molecules form rings or branched chains. Straight chain alkanes like octane C8H18 (octane number =0) produce low quality petrol which burns unevenly in a car engine. Rings and branched chain molecules burn more evenly and produce high quality petrol. E.g. 2,2,4-trimethylpentane has an octane number of 100. Task 1.7.2c.4 Draw fully displayed structural formulae for heptane, octane, 2,2,4-trimethylpentane and methylbenzene. 1.7.2d Alternative fuels Liquid fuels have the advantage of having higher densities than gaseous fuels. More energy may be stored in a liquid fuel than in the same volume of gaseous fuel. Petrol is a typical liquid fuel which can be thought of as mostly octane. It has two important properties namely volatility and octane number. Octane number is a measure of how smoothly the fuel burns. If a fuel ignites too soon in an engine the engine does not run smoothly or efficiently. The composition of petrol must be changed during the year to give the best values for these two properties. Fuels can be compared by looking at their relative energy values, handling characteristics and their environmental impact. Most fuels release CO2 which is know to increase global warming (a greenhouse gas) Fuelstateenergy per masshandlingenvironmenthydrogenGas(liquid at very high pressure very low temp)very highvery hard to contain and transfer only product is watermethanegas(liquid at high pressure)highhard to transfer burns cleanly CO2 and water formed may release SO2 (fossil fuel)butaneliquid (under pressure)higheasy to liquify and use liquidas for methane (fossil fuel)Octane (petrol etc)liquidhigheasy to handleas methane but some CO formed, engines also release NOx (fossil fuel)ethanolliquidmoderateeasy to handlecan be made for renewable sugar caneTask 1.7.2d.1 Hydrogen buses are running on a few select routes in the City of London. Explain why this is happening and why few cars have so far been manufactured to use hydrogen. During the second world war (a time a severe fuel shortages) a few vehicles could be seen driving around with huge canvas bags of methane on top of them. Why is methane gas not used like this today and how could it be used? Butane is the main fuel used by residents in American trailer parks. What advantages does it have over methane? What is the main use of octane and why is it valuable for this purpose? How sustainable is this use? Is ethanol a suitable replacement for petrol? Explain your answer. 1.7.2e Reactions of alkanes Alkanes burn in oxygen (air), their flammability being a hazard. Complete combustion is more likely with shorter alkanes and when plenty of oxygen is available. Incomplete combustion forms soot and carbon monoxide. CH4 (g) + 2O2 (g) --------> 2H2O (l) + CO2 (g) 2CH4 + 3O2 ---> 2CO + 4H2O carbonFormed by incomplete combustion as soot. It is bad for the lungs and disfigures buildings.Carbon MonoxideThis is produced by traffic and some gas fires. When inhaled by people CO replaces oxygen in the haemoglobin, however, CO is not easily lost again so eventually leads to suffocation. HYPERLINK "http://www.drbateman.net/gcse2003/gcsesums/chemsums/crudeoil/storyc4.15.htm" Story 1.7.2e Task 1.7.2e.1 Write equations for the complete or incomplete combustion of other alkanes. Answers 2C2H6 + 7O2 ( 4CO2 +6H2O C2H6 + 2.5O2 ( 2CO +3H2O Alkanes react with chlorine by a mechanism of free radical substitution. The reaction occur at room temperatures in inert solvent in the presence of UV light. CH4 (g) + Cl2 (g) --------> CH3Cl (g) + HCl(g) C6H14 (l) + Cl2 (g) --------> C6H13Cl (l) +HCl(g) Task 1.7.2e.2 Write an equation for making chloroethane from ethane. Name the possible products from a reaction between chlorine and ethane? How do you make 2-chloropropane from propane? How do you make 1,2-dichloroethane from ethane? Homolytic, free radical substitution (alkanes with chlorine)  HYPERLINK "http://www.drbateman.net/asa2sums/sum5.3/orgmechs.ppt" Presentation of all mechanisms - (needs Powerpoint) Substitution reaction is defined as the replacement of one atom (or group of atoms) in a molecule by another atom ( or group ). E.g. Reaction between methane and chlorine to form hydrogen chloride & chloromethane. The reaction is exothermic but energy in the form of U.V. light must be supplied to initiate the reaction. Chlorine absorbs the U.V light, the energy which is equal to approx. 400 kJ/mol. This is greater than the bond strength of the Chlorine molecule which then splits into Cl atoms. This is homolytic fission as the same number of electrons from the bond are passed to each atom. Free radical substitution has 3 steps. The half arrow is the movement of one electron. step 1: Initiation Cl---Cl ----> 2Cl. Each atom retains one electron from the covalent bond between the atoms. An atom or group of atoms which posses an unpaired electron is called a free radical. step 2: Propagation Each chlorine atom then reacts with a molecule of methane by abstracting a hydrogen atom to form hydrogen chloride and a methyl radical.  INCLUDEPICTURE "http://www.drbateman.net/asa2sums/sum5.3/sum5.35.gif" \* MERGEFORMATINET  INCLUDEPICTURE "http://www.drbateman.net/asa2sums/sum5.3/sum5.36.gif" \* MERGEFORMATINET   INCLUDEPICTURE "http://www.drbateman.net/asa2sums/sum5.3/sum5.35.gif" \* MERGEFORMATINET  H3C---H + Cl. -----> CH3. + HCl The methyl radical reacts with a molecule of Chlorine to form chloromethane and a Cl atom:  INCLUDEPICTURE "http://www.drbateman.net/asa2sums/sum5.3/sum5.36.gif" \* MERGEFORMATINET  INCLUDEPICTURE "http://www.drbateman.net/asa2sums/sum5.3/sum5.35.gif" \* MERGEFORMATINET  INCLUDEPICTURE "http://www.drbateman.net/asa2sums/sum5.3/sum5.36.gif" \* MERGEFORMATINET  H3C. + Cl---Cl ----> CH3Cl + Cl. step 3: Termination Radicals combine  INCLUDEPICTURE "http://www.drbateman.net/asa2sums/sum5.3/sum5.36.gif" \* MERGEFORMATINET   INCLUDEPICTURE "http://www.drbateman.net/asa2sums/sum5.3/sum5.35.gif" \* MERGEFORMATINET  H3C. + Cl. ---> CH3Cl In reactions 1 and 2 covalent bonds are broken so that one electron of the pair in each bond becomes associated with each of the atoms or groups. These are examples of homolysis or homolytic fission.  HYPERLINK "http://www.drbateman.net/asa2sums/sum5.3/freerad.htm" see an animation of homolytic, free radical substitution Task 1.7.2e.3 Make models to show the steps in the mechanism for chloination of methane. Draw out the mechanism for the reactions of chlorine with ethane to make chloroethane, and chlorine with dichloromethane. 1.7.3 Alkenes 1.7.3a Alkene formulae and bonding The general formula for alkenes is CnH2n. H H \ / C=C e.g. ethene C2H4 / \ H H The functional group is the carbon to carbon double bond. The molecule is unsaturated because of the double bond. Bonds form when orbitals overlap allowing electrons to be shared. Orbitals may be s orbitals or p orbitals. End to end overlapping gives sigma bonds. ( s )  INCLUDEPICTURE "http://media-2.web.britannica.com/eb-media/54/3254-004-AEC1FB42.gif" \* MERGEFORMATINET   INCLUDEPICTURE "http://media-2.web.britannica.com/eb-media/54/3254-004-AEC1FB42.gif" \* MERGEFORMATINET  P orbital s orbital Separate s and p orbitals sigma bonds between orbitals  SHAPE \* MERGEFORMAT  Sideways overlap of orbitals leads to pi bonds. (p) Separate p orbitals pi bonds between p orbitals  Alkenes are much more reactive than alkanes, this is rather surprising at first as a double bond would be expected to be stronger than a single one, and therefore more stable. The bond energy of a double bond is greater than that of a single bond, though not twice as great, compare 346kJmol-1 with 598kJmol-1. This would suggest that the two bonds in C=C may not be identical. In fact, two kinds of covalent bonds are involved:  HYPERLINK "http://www.drbateman.net/asa2sums/sum2.2/ethene1.ppt" bonding in ethene - (powerpoint needed) 1.7.3b Geometric cis-trans or E-Z isomerism Geometric isomers exist for some compounds with C=C double bonds in their molecules. No rotation is possible around the double bond so different compounds result if atoms or groups are in positions on the same side or opposite sides of a double bond. For example 1,2-dichlorethene can have its two chlorine atoms on the same side (cis) or opposite sides (trans) of the double bond. Z stands for the German word zusammen meaning together i.e. cis. Give atoms attached to one C atom high priority if they have higher atomic numbers. Take the atoms with highest priority either side of the double bond as cis or trans. Cl Cl cis-2,3-dichlorobut-2-ene Cl CH3 trans-2,3-dichlorobut-2-ene \ /Z-2,3-dichlorobut-2-ene \ / E-2,3-dichlorobut-2-ene C=C C=C / \ / \ CH3 CH3 CH3 Cl  HYPERLINK "http://www.chemguide.co.uk/basicorg/isomerism/ez.html" Full explanation of E-Z system. Task 1.7.3b: Draw and name both geometric isomers of 1,2-dibromopropene, 1,2-dichloroethene, 1,2 -dibromopent-1-ene, 1.7.3c Limits of the cis-trans naming system When the atoms on different c atoms are different then the naming cis or trans does not work. E.g.  INCLUDEPICTURE "http://www.chemguide.co.uk/basicorg/isomerism/ez2.gif" \* MERGEFORMATINET  Task 1.7.3c Draw and name geometric isomers of the following: 1-bromo-1-fluoro-2-chloroethene, 1-iodo-1-chloroprop-1-ene 1.7.3d Reactions of alkenes Hydrogen adds to an alkene in the presence of a nickel catalyst at 150oC. CH2 = CH2 + H2 --------> CH3CH3 Task1.7.3d.1 draw full displayed structural formulae for the above reaction. Describe how the following alkanes can be formed from a suitable alkene giving chemical equations; propane, butane, pentane, 2-methylpentane and 2-methylpropane. alkenes with halogens H2C = CH2 (g) + Cl2 (g) ---------> ClCH2CH2Cl (l) This reaction occurs in the gas phase. CH2 = CH2 + Br2 --------> BrCH2CH2Br red colourless This reaction occurs in an inert solvent like volasil. Both of these are addition reactions which occur at room temperature. The decolourisation of bromine seen in the second reaction is a good test for an alkene. Task1.7.d.2 Draw full displayed structural formulae for the above reactions. Describe how bromine reacts with propene, but-2-ene, pent-1-ene, 4-methylpent-1-ene, 2-methylpropene. alkenes with hydrogen halides Conditions: HX in gas phase or in non-aqueous solvent. Reaction type: electrophilic addition. The reactivity of these compounds, changes with bond strengths: HF < HCl < HBr CH3 CH2Br (g) When hydrogen halides add to an unsymmetrical alkene, 2 products are possible: CH3CH = CH2 (g) + HBr (g) ----------> CH3CHBrCH3 (l) Note CH3 CH2 CH2Br (l) is not formed Markownikoff's rule applies which states that the hydrogen attaches to the carbon holding the most hydrogen atoms. Task1.7.3d.3 Draw full displayed structural formulae for the equations above. Describe how HCl reacts with ethene, propene, but-2-ene, but-1-ene and 3-ethylpent-1-ene. Name the products in these reactions. alkenes with manganate(VII) Conditions: aqueous acidic or alkaline manganate (VII) Reaction type: oxidation: Acidified potassium managanate(VII) is decolourised by an alkene and a diol formed. 5CH2 = CH2 + 2H2O + 2MnO4- + 6H+ -----> 5HOCH2CH2OH + 2Mn2+ ethane -1,2 -diol Task1.7.3d.4 Draw full displayed structural formulae of the above organic compounds. Describe how to make propane-1,2-diol, butane-2,3-diol and 3-methylpentane-2,3-diol. 1.7.3e Heterolytic, electrophilic addition Addition mechanisms Bromine and hydrogen bromide with ethene Heterolytic fission- In this type of fission the two shared electrons in the bond are split unequally between the two atoms. One of the atoms keeps both electrons. As a result ions are formed. An electrophile is a species which attacks a carbon atom by accepting an electron pair. It is thus a Lewis acid Ethene reacts with bromine to form 1,2-dibromoethane: This is an addition reaction The cation C2H5 +, and other cations in which a carbon atom bears the positive charge, are given the general name carbonium ions. They may also be called carbocations. In the first step the two electrons which form the new bond are both provided by the alkene: thus, the reagent ( Br or Cl) is described as electrophilic ( i.e `electron-seeking'). CH2  INCLUDEPICTURE "http://www.drbateman.net/asa2sums/sum5.3/arrow2.gif" \* MERGEFORMATINET CH2+ || INCLUDEPICTURE "http://www.drbateman.net/asa2sums/sum5.3/arrow2.gif" \* MERGEFORMATINET  + Brd+-Brd- ---------> | + Br - CH2 CH2Br CH2+ INCLUDEPICTURE "http://www.drbateman.net/asa2sums/sum5.3/arrow.1.gif" \* MERGEFORMATINET  CH2Br | + Br ----------> | CH2BrCH2Br  INCLUDEPICTURE "http://www.drbateman.net/asa2sums/sum5.3/arrow2.gif" \* MERGEFORMATINET  means the movement of a pair of electrons.  HYPERLINK "http://www.drbateman.net/asa2sums/sum5.3/electadd.htm" see and animation of  HYPERLINK "http://www.drbateman.net/asa2sums/sum5.3/electadd.htm" heterolytic, electrophilic addition Ethene reacts with hydrogen bromide to give bromoethane: This is also an addition reaction. The first step is the formation of two ions, the ethyl cation and the bromide anion: The two ions then rapidly combine to form the product. In this reaction, the partially charged atom in hydrogen bromide is the electrophilic reagent. Hd+ -Brd- Since organic reactions involving heterolytic fission of bonds produce ions, these reactions tend to take place in polar solvents. Task 5.3(b)(iii) Describe with drawings the mechanisms for the reaction of HBr with ethene, HCl with ethene and Chlorine with propene. Hydrogen bromide and propene Two products are possible for this reaction. These are 1-bromopropane or 2-bromopropane. CH2  INCLUDEPICTURE "http://www.drbateman.net/asa2sums/sum5.3/arrow2.gif" \* MERGEFORMATINET CH3 || INCLUDEPICTURE "http://www.drbateman.net/asa2sums/sum5.3/arrow2.gif" \* MERGEFORMATINET  + Hd+-Brd- ---------> | + Br - CH +CH | | CH3 CH3 +CH2 CH3 | + Br ----------> | CH2Br CH2Br | | CH3 CH3 This is an example of Markownikoffs rule. The carbon atom with most hydrogen gets more. 1.7.3f Tests for C=C Add a few drops of aqueous bromine to an alkene. The red/orange colour of the bromine will be decolourised. Aqueous bromine contains many species. Br2(l) + (aq) ( Br2(aq) Br2(aq) + H2O ( H+(aq) + Br-(aq) + BrO-(aq) H2O ( H+(aq) + OH-(aq) One possibility is the formation of a compound which has a Br (bromo) group and an OH (hydroxyl) group attached. E.g. CH2  INCLUDEPICTURE "http://www.drbateman.net/asa2sums/sum5.3/arrow2.gif" \* MERGEFORMATINET CH2+ || INCLUDEPICTURE "http://www.drbateman.net/asa2sums/sum5.3/arrow2.gif" \* MERGEFORMATINET  + Brd+-Brd- ---------> | + Br - CH2 CH2Br CH2+ INCLUDEPICTURE "http://www.drbateman.net/asa2sums/sum5.3/arrow.1.gif" \* MERGEFORMATINET  CH2OH | + OH ----------> | CH2BrCH2Br Task 1.7.3f Draw fully displayed structural formulae for products from the reaction of propene with aqueous bromine. 1.7.3g Polymerization of alkenes A polymer, e.g. polyethene, is a long molecule made of smaller units called monomers, e.g. ethene. Some examples are shown below: MonomerPolymerPropertiesUsesethene CH2=CH2polyethene -(CH2-CH2)n-low mp. soft, flexibleplastic bags, squeezy bottles, washing up bowls, bucketspropene CH3CH=CH2polypropene -(-CH(CH3) -CH2-)n- high tensile strength water repellent low melting point low density, tougher than polyethene ropes, sacks carpets and curtains ropeschloroethene (vinylchloride) CHCl=CH2polychloroethene (polyvinylchloride PVC) -(-CHCl-CH2-)n-harder, less flexible than polyethene, electrical insulatorraincoats, guttering, floor tiles, packaging, covering electrical wiretetrafluroethene CF2=CF2polytetrafluroethene -(-CF2-CF2-)n-low friction on surfacenon-stick coatings on frying pansphenylethene (styrene) C6H5CH=CH2poly(phenylethene) (polystyrene) -(-CH(C6H5)-CH2-)n-softens at low temperature thermal insulatormoulded shapes coffee cups foam packagingTask 1.7.3g Draw displayed structural formulae to show the monomers and the polymers above. 1.7.3h Sustainability of polymers Energy is used to make, use and dispose of polymers: extraction, transportation, refining, cracking, polymerization, manufacturing processes for plastic objects. Non fossil fuel energy sources can increase the sustainability of these processes. Resources are use to make polymers: increasingly rare crude oil is currently the main raw material. Resources are saved by using alternatives such as paper bags in place of plastic ones. Reusing plastic bottles or bags saves resources also. Recycling plastic waste is possible for thermoplastics (those that melt rather than decompose on heating). Mechanical recycling involves careful sorting then melting or shredding waste plastic before producing plastic granules. The granules are made into new plastic objects. High quality recycled plastic can be made into the same type of object again. Low quality plastic is turned into less valuable objects. Chemical recycling cracks the polymers into their monomers which after separation can be polymerized back into the correct plastic. Biopolymers are made from sustainable plant starch or cellulose. These are environmentally valuable as they are biodegradable. Disposal methods include incineration. This releases energy but risk forming toxic gases like HCl, dioxin and HCN especially in back gardens. Industrial incinerators use pollution control systems to limit the release of toxins. Chemical decomposition can be used to convert the plastics to an industrial fuel called syngas (hydrogen + carbon monoxide). Plastic sent to landfill is non-biodegradable so poses risks to wildlife. All energy and resource inputs are lost if landfill is used. The carbon footprint is the level of carbon emissions. These result from: fossil fuel energy inputs and incineration of the polymer. Life cycle analysis tracks the polymer from raw material extraction to disposal. At each step energy and resource inputs and outputs are measured. The lower the inputs the more sustainable the use of a plastic becomes. 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