ORGANIC CHEMISTRY Learning Objectives. State natural gas andl petroleum as sources of energy Describe peirleum as a mixture of hydrocar’ons and the separation of petroleum ito useful fractions by fractional distillation ‘Name the usefil fractions of petrotenm and state their uses Describe the issues relating to competing use of oil 14.1 Fuels and Petroleum FUELS + Fuels such as fossil fuels and hydrogen are substances which produce a large amount of heat energy during burning. * Natural gas (mainly methane), coal and petroleum are the three main components in fossil fuels. * They are organic compounds because they all contain carbon element as the main component in their structures, + Petroleum is a mixture of hydrocarbons. They are called hydrocarbons because they contain only the elements carbon and hydrogen, * The constituent hydrocarbons in petroleum have different b by fractional distilation * In the separation of petroleum, a fraction is a mixture of hydrocarbons within a particular range of boiling points. The hydrocarbons have similar number of carbon atoms and physical properties in each fraction. i Points, so they can be separated Fractional distillation of petroleum + In fractional distillation, petroleum is vapourised by heating before feeding into the distillation tower * The vapours are then condensed in the fractionating column at their respective range of temperatures so that different fractions of the petroleum can be collected. a uete petroeum ges (LPG): Ful cooking Ge Sa pete gunn Pn ‘sme naphtha: Feedstock for the chemical industries “Mnemonic: Lite Petr (Emm paraffin (kerosene): Fuel for heating, cooking and aircraft engines ==> diesel: Fuel for diesel engines => tub ing oils: Lubricants and as a source of petroleum, —— polishes and waxes ‘=> bitumen: For making road surfaces + The size and mass of hydrocarbons increase from the light fractions to the heavy fractions due to an increase in the number of carbon atoms in their molecules, @nun+ When the size and mass of hydrocarbons increase down the fractions, the physical properties show the gradual changes also. Physical properties down the fractions Explanation ~The intermolecular forces between molecules increase when the size of the molecules increases. Hence, more energy Is required to overcome the forces. >The percentage by mass of carbon in the molecules: Less flammable increases when the size and mass of the molecules increases, so the hydrocarbons become less flammable. ~The Intermolecular forces between molecules increase when the size of the molecules increases. Thus, the forces are difficult to overcome and the larger hydrocarbons become thick or waxy, so they do not flow easily. +The intermolecular forces between molecules increase when Low volatility the size of the molecules increases, so mote heat is required to break the forces to change their physicel state. Boiling points increases High viscosity + The smaller hydrocarbons have a high demand because they can burn easily, so they are useful as fuels for cars and in power stations, However, the separation of petroleum by fractional distillation cannot meet the supply and demand for the smaller hydrocarbons. + Cracking is a process in which large hydrocarbons are broken down to produce more sinaller hydrocarbons in order to meet their supply and demand. (We will lean about the cracking later.) Nophthe + Naphitha fraction is the main source of hydrocarbons. I is used as the chemical feedstock forthe production of a wide range of organic compounds. + Naphtha fraction is used in the following productions: ¥ As industrial solvents Inthe manufacture of cosmetics Inthe manufacture of paints Y- Inthe manufacture of hiome cleaning fluids Issues relating to competing uses of oil + Petroleum is @ finte energy resource because itis non-renewable, + The competing uses of oll in the world due to industralisation and population growth lead to high ‘demand for oil. This could result in the depletion of the resources in a shorter time. + tis also being used lergely as chemical feedstock in industries which can contribute to air pollution and water pollution. Resin ZS g CETGOL 1. (@_ Name three main components in fossil fuels. (b) Which source of energy contains mainly methane? a © GIN Pte Ltd2. (@) Petroleum is of ltie use in its raw state. itis separated by the process of fractional distillation into useful fractions. State two main applications for separating petroleum into fractions, (b) The diagram below shows the fractional distillation of petroleum. factionating colurnn —| I farnace petroleum [1] | heat Identity each fraction and give an example of application for each fraction. No, of carbon | Boiling point : Fraction | No- oF cal He Name Application 1 1-4 <40 2 5-10 40-75 t 3 7-14 75-150 4 u-16 | 160-250 5 16-20 | 250-300 6 20-50 | 300-350 7 >50 > 360 @wn3. (©) Study the following statements. Use the letter ‘T’ for true statement and ‘F* for false statement. {) Each fraction bolls over a fixed temperature in the fractionating column, {i) The smaller hydrocarbons are collected at the top ofthe fractionating ‘column because they have the lowest boiling points. (i) The boiling points decrease from the top to the bottom of the fractionating column. (jv) The colour of fractions become darker trom the lighter fractions to the heavier fractions. (¥) The viscosity increases from the lighter fractions to the heavier fractions, In other words, the lighter fractions flow more easily than the heavier fractions. (vi) The ease of combustion increases from the lighter fractions to the heavier fractions. (ull) The lighter fractions burn with less sooty than the heavier fractions. (@) Why's there a need to conserve petroleum? (b) State a problem caused by the competing use of of. Learning Objectives: Describe an homologous series Describe the alkanes an homologous serie of sured ydrocarbons Draw the srictireofbronehed and mrbranchedC, to Calkames ©. Define isomerism ane identity isomer Describe he properties of alkanes ‘nderstend that cracking importa to meet the demand for fractions containing smaller molecules 14.2 Organic Compounds HOMOLOGOUS SERIES + Arhomologous series is a family of molecules that has: ¥ Ageneral formula Similar chemical properties due to the same functional group Gradual change of physical properties (such as melting and boiling points, viscosity and flammability) as a result of increase in size and mass of the molecules © 61M Pett‘+ Afunetional group is an atom or combination of atoms which gives organic molacules distinctive chemical properties. * The table below shows some common functional groups in organic chemistry: Homologous Functional group General Nome owing formula CH, carbon-carbon WA Honea alkane single bond mi hei Bees pani carbon carbon CH,, ‘double bond ina C\Hayis0H Alcotol hydroxy —o-H n= 1,2,ete ©, :H,,,COOH Carboxylic acid ccorbeayi 1 —o-0-H | n=1,2, ete ° CH,,0, Fster inkage I —c-0— 2,3, ete Molecular formula + Amolecular formula summarises the types of elements and the total atoms in a molecule but no information on its arrangement of atoms, For example, Ethanol has a molecular formula of C,H,OH."The formula indicates that ethanol contains 3 elements (C, H and 0) and a total of 9 atoms only. ‘Structural formula * Structural forula shows how atoms are covalently bonded to one another inthe molecule. Al the bonds are displayed, for example, The stuctura formula of ethan. wo 4 —6—$0 8 How ‘Naming of organic compounds + Ine name ot an organic compound consists of a prefix and a suffix, +The prefic indicates the niumhar of earbon atoms in the compound, Prefix Meth Eth Prop But ‘Number of carbon atom 1 2 3 4 @wn+ The suffix indicates the homologous series, Suffix Homologous series —ane alkane —ene alkene =o alcoho! —oicacid | carboxylic acid (or organic acid) ALKANE HOMOLOGOUS SERIES + Alkanes ate obtained directly from the fractional distillation of petroleum. + Alkanes are homologous series of saturated hydrocarbons: < ‘A general formula C,H,,,., where m is the number of carbon atoms ¥ Contains carbon-carbon single bond. ¥- Simitar chemical properties YA gradual change in their physical properties + Saturated means that the molecule contains only carbon-carbon single bonds. Each carbon atom is covalently bonded to four other atoms, so no new atom can add to it anymore. + They are hydrocarbons which contain only elements carbon and hydrogen. + Each member differs by 1 C atom and 2 H atoms +The first four members of alkanes: Physical Molecular Bolling | states Condensed Name {formula | Stucturatformula | ping | at room formula temperature i Methane | CH, He 162 | Gas cH, H a Ethane | CHy Hyp 89 Gas CH,CH, Hou cf Propane | GH, | HEE FH) 42 Gas CH,CH,CH, HHH HoH OH OH ti tt Butane | C,H, |H—G—C—G¢—C—H] 0.5 Gas | CH,CH,CH,CH sth L,CH,CH,CH, HOH HH OGM Mote* When the size and mass of alkane molecules increases, a gradual change in the following physical properties Is observed 2s wel Boling point increases Y Density increases Sane loan a page 358 Y Viscosity increases oer s ¥ Flammability decreases Isomerism ‘+ For some alkane molecules, there are a few ways to draw their structural formulas: Unbranched or branched Y Unbranched: All carbon atoms connecting in a single continuous line Branched: There is/are carbon atom(s) not connecting in a single continuous line For example, Butane has two structural formulas: Structural formula | P i eatin FE mesomssinies i ‘single continuous line oH ~— only three C atoms join ina single continuous line, The other C atom is ‘branched out + Isomers are molecules which have the same molecular formula but different structural formula, For example, Since butane has two different structural formulas, butane has two isomers. Naming simple isomers of alkanes ‘+ Isomers of alkanes usually have branched chains called alkyl groups. An alkyl group is formed when a hydrogen atom from an alkane molecule is removed, Alkyl group Name 1 —CH, Methyl =H, Ethyl —OH. Propyl OwnTo name the isomers of alkanes: Vv STEP I: Look for the longest chain of carbon atoms which is called the main chain. The main chain is named after the unbranched alkane with the same number of carbon atoms. v STEP Us Identify the alkyl groups. Y STEP IN: Indicate the position of alkyl groups on the main chain. The position at which the alkyl {groups attached to the main chain must be the lowest possible number. For example, + The name ofthe main chain is pentane + ~The name of the main chain is hexane as it has five carbon atoms. as it has six carbon atoms. + ‘The alkyl group is methyl. + There are two methyl groups. + The position of the methyl group on +The positions of the methyl groups on the carbon atom of the main chain is the carbon atoms of the main chain the lowest when it is counted from the are the lowest when itis counted from right to left of the main ehain. the left to right of the main chain + Hence, the name of this isomer is + Hence, the name of this isomer is 2-methylpentane. 2,3-dimethylhexane, Worked example Which of the following sets of molecules are isomers? Explain. set MoH Hew eat) Eales eS ea eee etd ee oe ee t 7 Try HHA KOH a) a 4 sete HHH OHH HHH EEL EPEIH HEL FEE EH EE ff abet et han aA baal Hoon A © ol Pte LutSolution Set A, Explanation: Set A HHH HH fh DLE possible drawing Hee ee H on TPT ry possible arawing 1 HHH HOH All § C atoms can be joined ‘Only 4 C can be joined ina by one continuous tne continuous line; there fs 2.C ‘which is oranched out” Set B i pie HOC Hee i Ty H HOW HG Htc 1 H AIS Catoms can be johed All C atoms can be joined dyone continuous tne ayone continuous ine 5 Reaction of alkanes + Alkanes are generally unreactive because they are saturated, + They can undergo combustion, substitution and cracking reactions, Combustion +The reaction is exothermic + In complete combustion, alkanes burn with blue flame without smoke. ‘+ The complete combustion of alkanes can be represented by the following equation: General word equation: alkane + oxygen gas —> carbon dioxide + water Worked example 3 Combustion of ethane inthe ar Word equation ethane -+ oxygen —> carbon dioxide + water Chemical equation 2C,Hglg) + 70,{g) > 4CO,(g) + 6H,01) © Gite re tnt Phneetann At eed @aunx74 Combustion of propane in ait Word equation propane + oxygen —> carbon dioxide + water Chemical equation C.HJ@ + 50,(g)-> 3CO{g) + 4H,0(0 + During incomplete combustion, alkanes bum with yellow smoky flame. + The possible products from incomplete combustion of alkanes are: Y Soot (carbon) ¥- Carbon monoxide Y water The posible products formed from the combustion of altanes For example, or dices Incomplete combustion of methane in the air Siar + Soot Possible reaction 1 Carton monevide Word equation methane + oxygen — carbon monoxide -+ water Chemical equation 2CH,g) + 30,(@) > 2CO(g) + 44,011) Possible reaction 2 Word equation methane + oxygen —» soot (carbon) + water Chemical equation CH,(g) + O,{g) > Cls) + 2H,000 Substitution reaction + The reaction takes place in the presence of light as the catalyst. + Each hydrogen in an alkane is displaced one at a time by one molecule of halogen gas. For example, Matrane (CH) mies with coi as (CI,) in the presence of light to produce dichloromethane (CHCl) Stage I: The frst hydrogen is displaced from CH, \ : Hoan + tog a Hop + He) aT e Chemical equation: CH, + Cl, -> CH,CI + HCI © 6IN Pee LttStage Il: The second hydrogen is displaced from CH,Cl H H AEH + cet te Hp + oa a a Chemical equation: CH,Cl + Cl, > CH,Cl, + HCI Overall chemical equation: CH, + 2Cl, > CH,Cl, + 2HCI Cracking reaction + Smaller alkanes are useful because they can burn easily. When the size and mass increase, they become more difficult to bum because the percentage by mass of carbon in the molecules increases. Therefore, they are nat efficient as fuels. * Cracking is the breaking down of large alkane molecules to produce smaller useful molecules. + Cracking is carried out by using high pressures and temperatures without a catalyst. It can also be done in lower temperatures and pressures in the presence of a catalyst. + tis very important industrial process because it can cater to the demand for fuels by producing ‘smaller useful molecules, + Cracking hes two different pathways which lead to different product formation. Possible reaction 1 large alkane —> smaller alkane + alkenes For example, CygHyy > GgHyy + CyHyg Possible reaction 2 large alkane -> alkenes + hydrogen For example, CygHye > 2CyHhy + Hy + An experiment to illustrate cracking of alkanes: mineral wool saturated with porcelain liquid kerosene” chips alkenes ~ Liquid kerosene isa source of lange alkanes. Porcelain chips act as the catalyst for cracking of alkanes, ~ _Alkenes are produced and collected using the displacement of water. este eo tu ainOther important applications of cracking: + It produces hydrogen for manufacturing of margerine or ammonia in the Haber process. “+ It produces alkenes which are important for making plastics through addition polymerisation. Sea ae 1. (@) Most organic compounds are classified into their respective homologous series. Describe four general characteristics of the members in a homologous series. (®) @ Explain what is meant by a functional group. (i) Hence, complete the functional group for the following families of organic compounds. Homologous series | Functional group _| Name of functional group Alkenes Aicohols Carboxylic acids Esters () Why are alkanes classified as saturated hydrocarbons? Organic compounds are named according to the number of carbon atoms they contain and the homolagous series they belong to. The prefix (the first part) indicates the number of carbon atoms in a compound and the suffix the second par) indicates the homologous series of a compound (@) Write the prefix for the following number of carbon atoms in a compound, Number of carbon atom 1 2 3 4 Prefix 316 oom Peud(0) Write the homologous series which corresponds ta the following suffix. Suffix -ane -ene al -oic acid Homologous series 3. (@) Name two sources where alkanes are commonly found. (b) _Alkanes are saturated hydrocarbons. Define the following terms, (Saturated (Hydrocarbons (©) Whatis the general formula for alkanes? 4. Complete the table belowto show the information ofthe frst four members inthe alkane homologous series. Chemical name Chemical formula Structural formula e 61t ett37k ‘The members of alkane homologous series show a gradual change in their physical properties. Explain the following changes in their physical properties when the number of carbon atoms in the members increases down the homologous series. (@) Increase in meting and boiling points (6) Decrease in flammability (©) Increase in viscosity An alkane is found to have 12 carbon atoms. (@) Predict the molecular formula for this molecule. (®) What is the molecular formula for the next member after this alkane? (@) Explain why alkanes are not reactive generally (©) Write the balanced equations for the following alkanes when they burn in excess oxygen. @ Ethane Gi) Propane (© @ Whats incomplete combustion? i) Name the possible products formed during incomplete combustion of alkanes. (@ Alkanes can react with chlorine and bromine under a specific condition. It is called a substitution reaction. () Whatis a substitution reaction? ecu rel(i) Name the condition needed for the reaction to take place between alkanes and chlorine, Gli) Describe what happens during a substitution reaction between alkanes and chlorine. (iv) Complete the following substitution reactions of various alkanes. | w Hog soy 4 HOW I wert + Br— Bry A 4 pon saga Me 7 (White @ chemical equation to represent the conversion of 1 mole of C,H, nto C,H,Cl, by chiorine 8. (@)_ Whats meant by isomerism? (©) Explain what you would expect to observe in isomers of alkanes in terms of their physical properties and chemical properties. (Physical properties (i) Chemical properties (©) Draw all the possible isomers for pentane. © oiMPteud fa - ownThe diagrams below show the structural formulae of various organic molecules. Identify the respective sets of isomers. 9. z-9—0— = Toonz 10 Identify three sets of isomers. (@) First set of isomers {b) Second set of isomers. (©) Third set of isomers © 61M Pte ttt10. The heavier fractions present in petroleum is more than the lighter fractions. Hence, the heavier fractions are converted into lighter fractions by catalytic cracking industrially (a) What is meant by cracking? (©) Complete the following equations that show the cracking of various large alkane molecules. CH, > Hye * Cy yy > 2G,H, + 2... sronnnns + Hy (i) WY rane sone “> CH, + CH, + C,H, 30H, + 20 Hyg + CH, +H, (©) Discuss an objective for cracking the larger hydrocarbons into smaller hydrocarbons. Learning Objectives Describe the atenes as an homologous series of wasaturated hydrocarbons Draw the structures of branched and unbranched C, to C, alkenes Describe the manacture of alkenes Describe the difference between saturated and unsaturated Iyxdrocartons Describe the properties of alkenes State the meaning of polyunsanurated Describe the manufacture of mengarine B990c00 ALKENE HOMOLOGOUS SERIES + Alkenes are obtained from eracking of alkanes mainly + Alkenes are homologous series of unsaturated hydrocarbons ¥ Ageneral formula C,M,,, where mis the number of carbon atoms Contains carbon-carbon double bond Similar chemical properties ¥- Agradual change in their physical properties, + Unsaturated means that the molecule contains carbon-carbon double bonds (C = C). * In carbon-carbon double bond, each carbon atom in this type of bond is covalently bonded to three atoms only, so a new atom can be added to it. * Each member differs by 1 C atom and 2 H atoms. @uun‘The first three members of alkenes: Physical Molecular Boiling | states Condensed Name | “formula | Stuctural formula poinyec | at room formula temperature Ethene } C,H, 104 Gas CH,CH, iii Propere | GH, | H—G=G—F—H ~48 Ges CH,CHCH, H HHO OH ri lt auine | 04H, | H—O—C—P—F—H) —62 Gas_—_| CH,CHCH,CH, HOH J When the size and mass of alkane molecules increases, a gradual change in the following physical properties is observed as well: ¥ Boiling point increases Y Density increases Viscosity increases v Flammability decreases The ratio of C atom to H atom in alkenes is 1 : 2. ‘Alkenes are generally reactive because they are unsaturated. New atoms can be added to the carbon atoms that form the double bond. one of the bonds is broken ceach carbo stom bas one free electron ‘Sanne explanet 1 each carbon accepts respective ‘new ators XandY Alkenes can undergo combustion, polymerisation and addition reaction. ‘Chetnical reaction of alkenes Combustion The reaction is exothermic. In complete combustion, the reaction can be represented by the following: General word equation: alkene + oxygen gas > carbon dioxide + water © GIN Pre LaEd Worked example 1 Combustion of etinene in air Word equation ethene + oxygen —» carbon dioxide + water Chemical equation Hg) + 30Xg) > 2C0,(@) + 2H,0(0 Worked example 2 ‘Combustion of propene in alr Word equation bropene + oxygen > carbon dioxide + water BR Teper iy ess of carn inal een lavas Chemical equation be 85 7esince certo of C21 2C,H,(g) + 90,{g) > 6CO,(g) + 6H,0(1) Seatwave 1:2 + Alkenes burn with sootier flames than alkanes because the percentage of carbon by mass in alkenes is higher than that in alkanes for the same number of carbon atoms present in their respective molecules. Addition reaction Addition of hydrogen (hydrogenation) * Hydrogen is added to carbon-carbon double bond at high temperature and pressure, + Atransition metal catalyst such as nickel is used. + Alkenes change to alkanes after hycrogen atoms are added. General word equation: alkene + hydrogen —> alkane Seiacsaasiahdan secant Worked example Addition of hydrogen to ethene to form ethane Word equation ethene + hydrogen gas + ethane Chemical equation CH® + H,@) > He) * A polyunsaturated food substance contains more than one carbon-carbon double bond in its structure, + Hydrogenation is used to convert unsaturated fats into saturated. For example, vegetable oils are polyunsaturated, so they exist as liquid at room temperature generally. in making margarine, they are hardened to form margarine by adding hydrogen to some of the carbon-carbon double bonds (C = C), @ wunAddition of steam (hydration) + Steam and alkenes are passed over a catalyst such as concentrated phosphoric acid at high temperature, about 300 °C. + Alkenes are converted to alcohol after addition of steam. General word equation: alkene + steam -> alcohol Worked example Addition of steam to ethene to form ethanol Word equation ethene + steam — ethanol Chemical equation CH@) + H,0le) > C,H,0H00 Addition of bromine (bromination) + Bromine gas or bromine water is brown in colour. + Addition of bromine is an important test to distinguish alkanes from alkenes, When it reacts with alkene, bromine is decolourised. ¥ Inalkanes, bromine remain brown. No reaction will take place, For example, ‘Addition of bromine to alkene (or unsaturated molecules) \ | — bromine water (brown solution) A mixture of : ‘ums bromine colourless and alkene Bubbling of ethene into bromine water Word equation ethene + bromine > 1,2-dibromoethane (colourless) (brown) (colourless) Chemical equation C,H (@) + Brylaq) > C,H,Br,(20) Observation Bromine water is decolourised. Gut Pe Lut‘Addition of bromine to alkane (or saturated molecules) 4 | — bromine water +] (erown solution) | mixture imal coral J) own snd alkane Example Bubbling of ethane into bromine water Word equation ethane + bromine» NO REACTION (colourless) (brown) Observation Bromine water remains brown colour. Polymetisation 1 Polymerisation is a process of joining small identical units to form large molecules. Alkenes are unsaturated, They can be used to produce large molecules through polymerisation reaction. (Refer to addition polymerisation] n( CH, =CH,) = — - Sein where x and y are the positions of bromine atoms on the carbon atoms in @ carbon chain (©) The diagrams below show the addition of bromine to solutions of alkanes and alkenes. 4 4 +— bromine water bromine water alkane solution alkene solution fest tube 1 test tube2 ett rtetdComplete the table below to show the observations between the reaction of bromine with alkanes and alkenes, Colour of bromine water Test tube Before adding into the | After adding into the solution solution and shaken 1 2 (Why bromination is important in the study of alkanes and alkenes? (@) Complete the following chemical reactions. @ CH.+BR> @) CH + 8,3 arning Objectives: Describe the elcohol homologons series Draw the sircnwes of C10 C,aleohols Descrte he properties of alohols Describe the formation of ethanol Sate the uses of ethanol Describe the carboxylic ced hemologous series gar ges ALCOHOL HOMOLOGOUS SERIES The alcohol homologous series: Y Ageneral formula is C,H,,,,0H, where n is the number of carbon atoms Y Contains a functional group called hydroxyl, — 0-H ¥ Similar chemical properties Y Agradual change in thelr physical properties, oomreud Chemisty © Level Concenniat | earning | Z90‘+ The first four members of aleohols: Name | Molecular | structural formula pone | Condensed formula i Methanol | CH,OH Hp 64 HOH 4 ty Ethanol | OH0H | H-G—P—O—H 78 CH,CH,OH HOH iii Fropanol | cio | H—P—F—F—O-H 7 CH,CH,CH,OH ne) tie Butanol | OWH,OH |H—p—E—E—¢—O-H] 117 | CH.CH,CH,CHLOH HHH OH + Alcohols can dissolve in water but their solubility in water decreases as their size and mass increases, Production of alcohols Fermentation of sugar + Yeast is used to convert sugar into ethanol in the absence of oxygen, Carbon dioxide is produced as a byproduct also. General word equation: sugar > ethanol + carbon dioxide + The temperature must not be too high because it can denature the enzyme of the yeast. Fermentation will not take place, Timewater (est for presenceof CO, produced uring fermentation) |__ sugar solution and yenst at 40°C + Fermentation of sugar solution by yeast must take place without oxygen to produce etfianol, This is because ethanol is oxidised to ethanoic acid when oxygen is present. 390 ecu mete+ To achieve a condition without oxygen: ¥ A:stopper is used to prevent air from entering the flask Y Besides testing for the presence of carbon dioxide, limewater solution also helps prevents ait from entering the flask * Usually the fermentation process can produce a relatively low concentration of ethanol. When the concentration of ethianol becomes too high, it would kill the yeast. + Ethanol can be separated from the sugar solution after fermentation by the process of fractional distillation, *+ Ethanol has @ wide applications such as: ¥ In the manufacturing of alcoholic beverages Y Used as a fuel for vehicles Used as industrial solvents for making paints or perfumes Used as a raw material to make ethanole acid n of steam + Adgition of steam to alkene molecules can produce 2 wide range of alcohols using different alkenes. Chemical reactions of alcohols Combustion ‘+ Alcohols burn with a clean flame or blue flame without soot generally, + In complete combustion, the reaction can be represented by the following: General word equation: alcohol + oxygen gas > carbon dioxide + water Worked example 1 Combustion of ethanol in air Word equation ethanol + oxygen — catbon dioxide + water Chemical equation C,H_OH() + 30,(@) > 2C0,{@) + 3,00) Worked example 2 Combustion of propanol in air ‘Word equation propanol + oxygen -» carbon dioxide + water Chemical equation 2CJH,0H + 90,{e) > 6CO,(e) + 8H,0() + Ethanol is used as a fuel for vehicles in certain countries because ¥ it burns more efficiently without producing any soot, Y- itis renewable, Ye tntOxidation reaction + An aloohol can be oxidised into a carboxylic acid by adding one oxygen atom to it (at the same lima, 2 hydrogen atoms are removed). ‘+The oxidation can be done by either one of the followings: ¥ By bacteria in the air (in the presence of axygen gs) ¥ By oxidising agents ~ Acidified potassium manganate(Vil) ~ Aciaified potassium dichromate(V0) +The chemical equation for an oxidation: General word equation: alcohol + oxygen gas —> carboxylic acid + water Worked example Oxidation of propanol to propanoic acid Word equation propanol + oxygen —> propanoic acid + water ‘Chemical equation C,H,OH() + O,(@) > CH,COOH(aq) + H,000 + When alcoholic drinks are left in the open air, they turn sour due to the oxidation of ethanol by bacteria to ethanoic acid, They taste sour as itis one of the characteristics of an acid, + An experiment to illustrate the oxidation of ethanol: acidified potassium dichromate(Vi) and ethanol heat ~The colour of acidified potassium dichromate(VI) changes from orange to green. Acidified potassium dichromate(VI) is an oxidising agent which causes ethanol to oxidise into ethanoic acid while it itself is reduced, = When a blue litmus paper is dipped into ethanoie acid, it tums red. 1 507 (@) Name and write the functional group in alcohols. (b) What is the general formula for alcohols? eo nett |(©) Complete the table below to show the information of the first four members in the alcohol homologous series. ‘Chemical name ‘Chemical formula Structural formula 2. (a) Name a reaction that can be used to prepare various types of alcohols, (b) The diagram below shows another method to prepare an alcohol. (Name the reaction taking place in the flask. Name the alcohol produced from this reaction.4. (¥)_ The flask has an air-lock design to prevent air from entering the flask. Explain why itis 50. (i) Sugar has a chemical formula C,H,,0,. Write a chemical equation to show the fermentation of sugar. (vil) How can the product of alcohol be separated from the solution? (©) One of the applications of ethanol is used as an organic solvent. (Give two reasons why ethanol is widely used as an organic solvent. (State two other applications of ethanol. (a) Write the chemical equations for the complete combustion for the following alcohols. @ Ethanol (i) Propanol (b) State the type of flame produced from the buming of ethanol. oom rend) ) Explain why alcoholic drinks such as beer or wine turn sour when they are exposed to atmospheric air after a period of time. ‘The diagram below shows the laboratory reflux apparatus containing a mixture of ethanol and. aan oxidising agent. Refluxing of the mixture is carried out for a period of time. water out — |! condenser [jas wera y round bottom flask }— waterbath }— ethanol with oxidising agent Poe () Whatis the function of the condenser? (i) Name the oxidising agent used in this experiment. (ii) Describe what you would expect to observe when the reflux uf ethanol and oxidising agent is carried out. (iv) Write an equation to show the oxidation of ethanol () What would happen when a blue litmus paper is placed inside the solution after the reaction? Explain, wn(6) Propanol is oxidised in the presence of an oxidising agert. (Write an equation to represent this reaction. (ii) Name the acid formed in this reaction. Learning Objectives: [9 Deserite the earboxyic acid homologous series rave the siucturas of C, to C, carboxylic acids Describe the properties of carboxylic acids as weak acts Describe the formation of erhanoe acid Describe the reaction between carbaxyle acids and alcohols oform eters State the commercial uses of esters CARBOXYLIC ACID HOMOLOGOUS SERIES + The carboxylic acid homologous series: - Ageneral formula is C, ,H,, ,COOH, where n is the number of carbon atoms i Contain a functional group called carboxyl, —C—O—H ¥ Similar chemical properties Y Agradual change in their physical properties + The first four members in catboxylic acid homologous series: Ta ag [ei conscas Name formuta ‘Structural formula point? formula . Methane acid | HCOOH j 11 00,4 H—C—O—H if Ethanoic acid | CH,COOH Hye 118 cH,CO,H 7 ti? Propanci cid | C,H,COOH | H—O— —c—o—H 414i CH,CH,CO,H HOH TET Butanic acid] C\H,COOH | HO eet 164 | CH,CH,CH,CO,H teen 26 MeLCarboxylic acids are weak acids. They ionise partially in water to produce hydrogen ions, For example, Molecules of ethanoic acid ionise partially to produce hydrogen ions in water. CH,COOH(ag) <= CH,COO aq) + H'teq) + Therefore, they have similar properties with other acids: ¥ Sour taste ¥ Tur blue litmus paper red Y React with metals, carbonates and alkalis/bases to form salts Chemical reaction of carboxylic acids Reaction with metals + Carboxylic acids react with metals to produce salt and hydrogen. General word equation: acid + metal — salt + hydrogen Worked example Reaction between potassium and ethanoic acid Word equation Potassium + ethanoie acid -> potassium ethanoate + hydrogen Chemical equation 2Kis) + 2CH,COOH(aq) > 2CH,COOK(aq) + H,(@) Reaction with carbonates + Carboxylic acids react with carbonates to produce salt, carbon dioxide and water. General word equation: acid + carbonate > salt + carbon dioxide + water Worked example Reaction between magnesium carbonate and propanoic acid Word equation ‘Magnesium carbonate + propanoic acid + magnesium propanoate + carbon dioxide + water Chemical equation MgCO,(s) + 2C,H,COOH(aq) ~ (C,H,COO),Mglaq) + CO,(e) + H,0(0 Reaction with alkalis/bases + Carboxylic acids react with bases/alkalis to produce salt and water. General word equation: acid + base/alkali ~> salt + water ots Pret m eee @wnEster Worked example 1 Reaction between lithium hydroxide (an alkali) and ethanoic acid Word equation Lithium hydroxide + ethanoic acid — lithium ethanoate + water Chemical equation LiQH(aq) + CH,COOH(aq) -> CH,COOLitag) + H,0(0 Worked example 2 Reaction between calcium oxide (a base) and methanoic acid Word equation Calcium oxide + methanoic acid —> calcium methanoate + water Chemical equation CaOIs) + 2HCOOH(aq) -» (HCO0),Caleq) ++ H,01l) Carboxylic acids can react with alcohols to form esters by the process of esterification, General word equation: carboxylic acid + alcohol > ester + water (See the ester homologous series) ESTER HOMOLOGOUS SERIES Esters are molecules with sweet-smelling properties. They are used as ingredients mainly in perfurnes or as artificial flavourings in food. Esters can be produced from the reaction between a carboxylic acid and an alcohol. Water is produced in the reaction as well. ‘The reaction is called esterification. Concentrated sulfurie acid solution acts as the catalyst in this reaction Y- Aicohol: loses ~OH atoms Carboxylic acid: loses -H atom haa ‘ethanoic acid propanol ems = thoge He fet lic H— Cc ooo H + HO T TS (oes Go A tren Host by alcohol) © GUM Pre Led9 + Thorinkage ot lL ___ is calles the ester inkage which i leo the functional group of esters. + Toname an ester: ¥ Alcohol: ~anol -> -y1 Carboxylic acid: ic acid > ate For example, To name an ester formed by propanol and ethanole acid propyl ethanoare ~ fiom propanol from ethanol acid eae LE 1. (@)_ Name and write the functional group in carboxylic acids, (©) What is the general formula for carboxylic acids? (©) Complete the table below to show the information of the fist four members in the carboxylic acid homologous series. Chemical name ‘Chemical formula Structural formula pin prea 7 aun(@) Write the word equations when ethanoic acid reacts with the following substances. (Reaction with sodium (i) Reaction with magnesium carbonate Gil) Resection with potassium hydroxide (b) The chemical equation shows ethanoic acid, an example of carboxylic acids, in water. CH,COOH(aq) = CH,COO*(aq) + H"(aq) Explain why carboxylic acids are considered as weak acids. (©) Butanoic acid is a carboxylic acid. It is added into sodium hydroxide. () Write an equation to show the reaction between butanoic acid and sodium hydroxide. (ii) Name the salt formed in this reaction. Alcohols can react with carboxylic acids to form ester. (@) Write the word equation to represent the reaction between alcohols and carboxylic acids. (b) Name this type of reaction. (©) Name a catalyst used for this reaction, (@) Name and write the functional group in esters. (©) State a physical property of esters that are different from other organic compounds, oO oom Pend4. (a) Complete the table by naming the substances involved in the formation of esters. The first row has been done for you. Alcohol | Acid Ester Ethanol Propanoic acid Ethyl propanoate @ Methanoic acid Propy! methaonate w@ Butanol Butyl butanoate w Pentanol Ethanoie acid ww Methyl butanoate (b) Complete the table below by drawing the respective structural formulae for the respective substances involved in the formation of esters. Alcohol Acid Ester HO Io 0 nope 0nd 4 o HH ° i tl w 4 H—C—0—¢—C—H H—C—O—H Id wow How HHO HH I I | Voit i i a pope tn HOW HOH HOW | nO | iol ) spon p H H (©) Write the chemical equations for the following reactions, (Between ethanoic acid and propanol (i) Between propanoie acid and methanol eomPtete Phrnemtetns 1 sel a annoAn Leaning Objectives: Deseribe macromolecules Describe addon polymerisation eg. polyfethene) from ethene as monomers Slate the uses of paly(ethene) ‘Dedhce the structure of polymer from a monomer and vice versa Describe nylon and Terylene as condensation polymers and the partial structure ofrylon and Terplene ‘State the uses of nylon and Terylene Describe the pollution problems caused by non-biodegradable plastics 14.3 Macromolecules MACROMOLECULES + Macromolecules are substances containing large number of atoms, such asproteins, carbohydrates, or synthetic polymers. + Polymers are large substances formed from many identical small molecules bonded together. + Polymerisation is the process that joining many identical small units of molecules known as ‘monomers to form a large molecule (a polymer). + There are two types of polymerisation: Addition polymerisation Y Condensation polymerisaticin Addition polymerisation + The monomers used in polymerisation are unsaturated, i.e. containing carbon-carbon double bonds. n( CH, =CH,) —> —tCH, Hag large number of monomers ‘+ There Is no loss of atoms in adcition polymerisation. + The three important products from this type of polymerisation are poly(chloroethene) or PVC, poly(ethene) and perspex. Formation of poly(ethene) Monomer used: Ethene Polymer formed: Polyfethene) Uses of polyethene) : Plastic bag or clingfilm The mechanism = mou eu Ep om SEP 2 Git PettDeducing monomer used in a polymer + For each monomer, it contains carbon-carbon double bond. + During polymerisation, one of the C = C bonds is broken so that it can be joined to the adjacent molecules. To deduce the monomer from a polymer, pick any two carbon atoms in the carbon chain and place the C = € back to it. The monomer used in that particular polymer can be Identified, Worked example 1 46H oH tte if —c—c—c-c— => oF Tet Aw 4H Podmer: oyctraten) a PVC Horanwe: Chonatene i Worked example 2 H CO,CH, H CO,CH, CO.CH, H i eee a | eee H CH; H CH, CH, H Polymer: Poly(methyimethacrylate) or Perspex Monomer: Methylmethacrylate Condensation polymerisation + The polymers are formed by two different monomers in alternate positions. For example, Ifthe monomers are A and 8 ‘The structure of the polymer: —A—B—A—B—A—B— Two synthetic polymers made from the condensation polymerisation: ¥ Nylon ¥ Terylene ‘Nylon + Nylon is called polyamide because it contains a large number of amide linkage, —CO—NH—, in the polymer. Its useful in making fishing lines, parachutes, sleeping bags and climbing ropes. + Two types of monomers used: 9 ° 4 H I i and | | H-0—C—]—Ct—0—# HN —EESI-N—H dicarboxylic acid diamine aun‘The formation of nylon: T i i ii + HO—c oc HEN Nt z= removed 10 amide Finkage t eens \ ale 4 | N ? —<- panial structure of nylon Terylene + Terylene is called polyester because it contains 2 large number of ester linkage, —COO—, in the molecule. + itis man-made fibre which is useful in making clothing. + Two types of monomers used: oo 9 I 1 and = HOO H-o0—C—[—]—-c—0—-# dicarboxylic acid diol ‘The formation of Terylene: i i + Hoc 0-4 H-Oo-E=I—0—-H +. removed wee, comes i i —c—]—-t— 0 ES—-0: + nH.) partial structure of Terylene Problems with synthetic plastics + Synthetic plastics are non-biodegradable, It means that they cannot be broken down easily by decomposers such as bacteria, Therefore, the landfill sites are full of plastic wastes which contribute to land pollution. + They release poisonous carbon monoxide gas when thay are burnt incompletely, contributing to air pollution. ane ecu mte ltdi a ea 1. (@)_ Whatis meant by macromolecules? () (@ Whatis a polymer? (ii) What is the term used to describe a small repeating unit in a polymer? (©) (@ Whats polymerisation? (i) Name the two types of polymerisation. wu wa addition monomer polymer (a) Name the monomer. (b) Explain why this type of polymerisation is called an addition polymerisation, (©) Name the polymer formed, (@)__ Write a structural formula, by showing one repeating unit, to represent this polymer. (©) State two functions ofthis polymer, (f) One part of the poly(ethene) is formed by 10 000 units of this monomer, Determine the relative molecular mass of this part of poly(ethene)..(@) Thetable below shows fewtypes of polymers made by the process of addition polymerisation. rita the structural formulae for monomers and polymers in the blank provided. Monomer Polymer HoH OW OH | It 0 fee teu ee i H HGH OH, ® (tt Let ON HCN H ii) (iv) (a) Whatis meant by a condensation polymerisation? (i) Name two polymers that are formed by condensation polymerisation (ii) Name the small molecule produced from the condensation polymerisation. (b) The diagrams below show part of the process of condensation polymerisation. icarboxylie acid diol 9 I i H-o—c—MMll- c= HoT 0-4 condensation 2g polymensaion 40 ‘polymer (Nate the polymer. eanPett() © (i) Deduce a reason to explain why the monomers are called dicarboxylic acid and diol respectively ii) During the formation of the polymer, what happens to dicarboxylic acids and diols? (WN) Circle an ester linkage on the diagram. (W)_ State an application of Terylene, Nylon is a polymer formed by two repeating units of monomers. They are dicarboxylic acids and diamine. The diagram below shows part of nylon structure. iit ti PON EI CAT 6 4 H Draw the structural formulae for the monomers present in nylon. (i) How are amide linkages formed in the nylon? (ii) Circle the amide linkage on the diagram. (iv) Explain why nylon is known as polyamide. (W) State three uses of nylon. One of the properties of synthetic (man-made) plastics is nor-biodegradable. @ Explain what is meant by non-biodegradabie. (i) What is the undesirable outcome of plastics being non-biodegradable? State and explain another problem caused by synthetic plastics. nunaed treat Section A: Multiple-Choice Questions 1. Which of the following molecules belongs to alkene homologous series? A. CagHey Be CH C. CaHye De CH 2. Which of the following reagents can be used to differentiate a sample of propane from propene? A. Limewater 8. Lighted splint C. Bromine water D. Acidified potassium dichromate(VI) 3. What is the formula of the ester formed when ethanoic acid reacts with propano!? A. CH,CO,CH, B. CH,CO,C,H, C.C,H,CO,C,H, DB. CH,CO,C,H, 4, Which of the following is not one of the isomers? HHH HH HH HH tii Tee Ee iT A 0) ne ape) HHH HH alan noon f Vv HoooH Lt la 4 Hoe W TH 4 I H-C—OTH HoG—o— GH T 1 | HOH 4 4 Al aw cm BV 5. Which of the following shows the products from the fermentation of sugar? ‘A. Carbon dioxide and water B. Ethanol and water C. Carbon dioxide and ethanol ©. Ethanol and hydrogen ano e GIN Pet6. The structural formula of a compound is shawn below, iii H-c=¢—¢7 OH ie o=c—o I A Which of the following homologous series is not found in this compound? A. Carboxylic acid B. Alcohol cc. Ester D. alkene 7. What are the products produced from the complete combustion of butanol in ait? ‘A. Soot and steam 8. Carbon monoxide and carbon dioxide C. Steam and carton dioxide D. Carbon monoxide and soot 8, The equation shows a molecule of an alkane being broken up into smaller molecules by heating to high temperature. TEttee ee Sa eae ea Ste HSU tI tetra ee UM ee H HH HH OH H HH H HH ‘What is the other product M?_ AL GH, B. CH, c. CH, D. GH, 9, The structure below represents part of a nylon. 4 ° 8 i Ti i ti c—[_]—c—N J—N C—C_—-c—N = ‘What is the repeating unit in this structure? 4 i 4 A B. ! I I NW NN : ma . ft i D ri —c--e— —-en -E— 10. Which of the following catalysts is used to prepare ethyl propanoate from ethanol and propanoic acid? A. Concentrated phosphoric acid B. Nickel C. Acidified potassium dichromate(V!) D. Concentrated sulfuric acid © 6INPteL @uwnSection B: Short Answer Questions 1. An organic compound has the following structural formula, jell | HoC—C erecreeaaea H | H HOH OH @ (b) Inwhich homologous series does this substance belong to? (©) Write down, for this molecule, @ molecular formula Gi) empirical formula (@) Suggest () the starting materials to prepare this compound (i) the name of this compound (e) Calculate the percentage by mass of carbon in this compound. 2, Butane burns in air to produce carbon dioxide and steam, (@) Write @ balanced chemical equation for this reaction, {b) How would you test for the presence of carbon dioxide? (©) Caloulate the volume of carbon dioxide formed, measured at rt.p., when 50 cm? of butane burns in excess of oxygen. ain © 61M Pre Lud@_ Give three characteristics of the homologous series of butane. 3. The following shows a sequence of chemical reactions. propanol “, propanoic acid 5 propyl propanoate (@) (At which stage, A or B, is acidified potassium dichromate(VI) added into the solution? (i) Explain the role of acidified potassium dichromate(V/) in the stage you named in (@)(). (b) Draw the structural formula of propanoic acid, (©) () _ Whatis the other material needed in stage B to produce propyl propanoate? i) Draw the full structural formuta of propyl propanoate. 4, Ethene gas is bubbled into bromine water. (a) Describe what you would expect to observe. (b) Name the reaction which gives rise to this observation, (©) Ethene is an unsaturated compound, Explain the term unsaturated. (@)_Asample of 7.0 g ethene burns in excess of air, carbon dioxide and steam are given off. (Construct a balanced chemical equation for this combustion. (Calculate the mass of steam produced from the combustion of 7.0 g ethene, ain ore - @aun5, An unsaturated molecule has the following structure. Br Br (b) This molecule has the similar chemical properties as ethene, Draw the structural formula of the compound formed when it undergoes addition reaction with steam. (©) This molecule is used as a monomer. When a large number of this monomer joins up together, it forms a polymer () What type of polymerisation do these monomers undergo? .. (Draw the structure of the polymer, showing six carbon atoms, which is formed by this ‘monomer. Section C: Free Response Questions 1. (@)_ The general formula of the alkane series of hydrocarbons is C,H,,,.. One member of this series contains 84.0 % by mass of carbon. (Determine the molecular mass of this alkane molecule. (i) Draw the full structural formula for this hydrocarbon. (b) Cracking is the breaking of larger alkane molecules into smaller useful molecules. The process can be demonstrated as follows. ceramic wool gaseous soaked in kerosene hydrocarbons broken pot’ (Whats the purpose of the broken pot? i) Kerosene contains propane. It undergoes cracking to form an ethene molecule. Predict the other produc. i) Calculate the maximum volume of ethene formed from 150 cm* propane measured atrtp. 2, (a). The diagram below shows part of a plastic structure. HHH te Se pee eee Laie boua () Draw the monomer used to make this polymer. i) Describe two problems caused by synthetic plastic. (©) Terylene is @ polyester. Draw a section of Terylene structure showing two repeating units. ven ecinprewt