CARBON COMPOUNDS 1.

Carbon compounds can be divided into a) Inorganic compounds i) Carbonates ii) Hydrogencarbonates/bicarbonates iii) Cyanides iv) Carbides ( example aluminium carbide) b) Organic compounds 1. Organic compounds are compounds that contains the element carbon bonded to other elements by covalent bonds. 2. Organic compounds was the term used originally to indicate compounds derived from living things. However many organic compounds can be synthesized in the laboratory. Hydrocarbons 1. Hydrocarbons are organic compounds that contain the elements carbon hydrogen only. 2. The molecular formula of hydrocarbons can be represented by CxHy , where x and y are whole numbers. 3. Organic compounds that have the same chemical properties are classified into families called homologous series. 4. Hydrocarbons are classified into 4 main classes : i) alkanes ii) alkenes iii) alkynes iv) arenes 5. Alkanes, alkenes and alkynes are called aliphatic hydrocarbons whereas arenes are called aromatic hydrocarbons. 6. Aliphatic hydrocarbons have linear or cyclic(ring) structures. 7. Aromatic hydrocarbons contain the benzene ring. Sources of hydrocarbons 1. The main sources of hydrocarbons are from three fossil fuel substances : a) petroleum(crude oil) b) natural gas c) coal 2. Petroleum is a mixture of hydrocarbons and some sulphur compounds. 3. Natural gas consists mainly of methane gas with a small amount of ethane. 4. Coal is a complex mixture of hydrocarbons with some nitrogen and sulphur. Alkanes 1. General formula CnH2n+2 where n = 1,2,3... 2. Alkanes are saturated hydrocarbons because the molecules contain only single bonds between carbon atoms. Naming of alkanes 1. The table shows the IUPAC names, molecular formula and structural formulae of the first 10 members of the straight-chain alkanes. 2. The molecular formula is a formula that shows the actual numbers of atoms of each element present in one molecule of the substance. 3. The structural formula is the formula that shows the arrangement of atoms and covalent bonds between atoms in a molecule of the compound.

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Name of alkane Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane

Molecular formula

Structural formula

Physical Properties of alkanes 1. As we go down the alkane series, the physical properties change gradually because of the gradual increase in the molecular size. 2. Alkanes have low melting points and boiling points because they exists as small neutral covalent molecules. When the relative molecular masss increases, the melting point and boiling point increases. 3. Methane, ethane , propane, butane are gases at room temperature. The alkanes from C5 to C18 are liquids while alkanes with C19 and above are solids at room temperature. 4. Alkanes are less dense than water. The density increases as the molecular sizes increase. 5. Alkanes are insoluble in water. 6. Alkanes are non-conductors of electricity because they are made up of neutral covalent molecules. Chemical Properties of Alkanes Reactivity of alkanes 1. Alkenes are saturated hydrocarbons that have strong bonds in their molecules. 2. Hence alkanes are less reactive than unsaturated hydrocarbons like alkenes. Combustion of alkanes 1. Like other hydrocarbons, alkanes burn readily in excess oxygen to produce carbon dioxide and water. General equation : CxHy + ( x +y/4)O2 xCO2 + y/2H2O 2. The number of carbon atoms per molecule increases as the molecular size of the alkane increases. Therefore the alkane becomes less combustible and produces a more smoky flame. Substitution reactions 1. In the absence of UV light, alkanes do not react with chlorine. 2. However when a mixture of alkane gas and chlorine gas is exposed to UV light(sunlight), substitution reaction occurs and a mixture of organic compounds are produced. 3. A substitution reaction is a reaction in which an atom or a group of atoms in a molecule is replaced by another atom or a group of atoms.

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4. In the reaction between methane and chlorine, under the presence of UV light, the hydrogen atoms in the methane are replaced step by step by chlorine atoms. CH4(g) + Cl2(g) CH3Cl(g) + HCl(g) CH3Cl(g) + Cl2(g) CH2Cl2(g) + HCl(g) 5. The rate of reaction between alkanes and bromine is slower than the rate of reaction between alkanes and chlorine. 6. Iodine does not react with alkanes.

Alkenes 1. General formula CnH2n , where n = 2,3,4 ... 2. Alkenes are unsaturated hydrocarbons. Alkene molecules contain at least one double bond between the carbon atoms ( C=C ). 3. The double bonds is the functional group of alkenes. Name Molecular Structural formulae formula Ethene C2H4

Physical Properties of alkenes: 1. Like alkanes, the physical properties of alkenes change gradually as the number of carbon atoms per molecule increases. 2. Alkenes have low melting points and boiling points because they consist of simple covalent molecules. The melting point and boiling point increases gradually on going down the alkene series. 3.The first three alkenes are gases at room temperature. Alkenes containing between 5 to 15 carbon atoms are colourless liquids while the higher alkenes are waxy solids at room tempeature. 4. Alkenes are less dense than water but the density increases gradually on going down the sies. 5. Alkenes are insoluble in water because the consists of simple, neutral covelent molecules. 6. Like alkanes, alkenes are non-electrical conductors. Chemical Properties of alkenes: Combustion of alkenes 1. Like alkanes, alkenes burn in excess of oxygen to produce carbon dioxide and water. 2. Alkenes burn with a yellow flame. The flame is more smoky than the corresponding alkanes. Addition reactions of alkenes 1. The double bond between the carbon atoms in the alkene molecules are unstable.

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2. Alkenes are very reactive and tends to undergo addition reaction to break the double bond. This reaction will convert the unsaturated hydrocarbon to saturated hydrocarbon. 3. Alkenes undergo addition reactions with the following reagents : a) Hydrogenation (addition of hydrogen) 1.A mixture of alkene gas and hydrogen is passed over nickel or platinum at 200oC. Example : the hydrogenation of propene to propane. Equation : 2. hydrogenation is used to make margarine (solid) from vegetable oils (liquid) b) Halogenation (addition of halogens) 1. When ethene is passed into liquid bromine ( or a solution of bromine in tetrachloromethane ), the brown colour of bromine is decolourised. Equation : 2. Bromination is used as a chemical test to identify unsaturated organic compounds. 3. Alkenes also react with chlorine (chlorination ). c) Reactions with hydrogen halides (HX) 1. The reaction occurs at room temperature. Example : Reaction of propene with hydrogen chloride gas. Equations : i) ii) d) Hydration ( addition of water ) 1. Alkenes do not react with under ordinary conditions. 2. When a mixture of ethene and steam is passed over phosphoric acid as catalyst at 300oC and pressure 60 atmosphere, ethanol is produced Equation : e) Reaction with acidified potassium manganate(VII) solution: 1. Acidified potassium manganate(VII) is also used to distinguished between unsaturated and saturated compounds. 2. The acid added to potassium manganate(VII) is sulphuric acid. Why is hydrochloric acid not used ? 3. When alkenes react with acidified potassium manganate(VII) solution, the purple colour of the manganate(VII) ions (MnO4-) , is decolourised. An organic compound (diol) is formed. Equation : e) Polymerisation 1. Under suitable conditions, ethene undergoes addition polymerisation to form polyethene (polythene). 2. The suitable conditions are : i) Temperature of 200oC and pressure of 1500 2000 atmosphere, without catalyst. ii) Temperature of 60 100oC and a pressure of 7 10 atmosphere with Ziegler catalyst. Equation : Activity : To compare the chemical properties of alkanes and alkenes Apparatus : Porcelain dish, dropper, Bunsen burner, wooden splinter Materials : Hexane, hexene, liquid bromine and acidified potassium manganate(VII) solution. a) Combustion of alkanes and alkenes 1. About 1 cm3 of hexane and hexene are placed separately in two porcelain dishes. 2. The liquids are ignited with a glowing splinter.

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3. A filter paper is placed above the flame to test the sootiness. B. Reactions with bromine 1. About 1 cm3 of liquid bromine is added to a test tube. 2. About 2 cm3 of hexane is added to the liquid bromine and the mixture is shaken gently. 3. The colour changed is observed and recorded. 4. Steps 1 t0 3 are repeated using hexene. C. Reactions with acidified potassium manganate(VII) solution 1. Three or four drops of potassium manganate(VII) solution are added to a test tube and about 1 cm3 of dilute sulphuric acid is added. 2. 2 cm3 of hexane is added to the acidified potassium manganate(VII) solution and the mixture is shaken. 3. The colour change is observed and recorded. 4. Steps 1 t0 3 are repeated using hexene. Results Test Combustion Reaction with liquid bromine Reaction with acidified potassium manganate(VII) Observation Hexane Hexene Burns with a smoky yellow Burns with a more smoky flame yellow flame The brown colour of bromine The brown colour of bromine is remains unchanged decolourised The purple colour of potassium The purple colour of potassium manganate(VII) remains manganate(VII) is decolourised unchanged

Discussion : 1. Hexene burns with a more sooty flame than hexane because hexene has a higher percentage by mass of carbon per molecule. 2. Hexene reacts with both bromine and acidified potassium manganate(VII) because hexene is an unsaturated hydrocarbon. Homologous Series 1. A homologous series is a family or group of organic compounds with the same functional group and wit similar chemical properties. 2. A functional group is an atom or a group of atoms that determines the characteristics of an organic compound. Characteristics of Homologous series 1. Members in the same homologous series have the same general formula. Alkanes - CnH2n+2 ; Alkenes - CnH2n ; Alcohols - CnH2n+1OH 2. Members in the same homologous series can be prepared using similar methods. Examples : Alkanes are prepared by the dehydration of alcohols using concentration sulphuric acid. 3. Members in the same homologous series show a gradual change in the physical properties. 4. All members in the same homologous series have similar chemical properties. 5. The molecular formulae of members in the homologous series differ from each other by the group -CH2. Isomerism 1. Isomers are compounds which have the same molecular formula but different structural formulae.

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Isomerism in alkanes 1. Isomerism exists in alkanes because of the existence of different carbon chains for the particular alkane straight chain and branched chain. 2. The isomers in alkane have different physical properties because they have different structures. However they have the same chemical properties because they belong to the same homologous series (family). 3. The following are the guidelines for writing the structural formulae of alkane isomers. Step 1 : Write all the possible carbon chains straight and branched chains. Step 2 : Complete the molecular structure by filling in all the single bonds. Then add hydrogen atoms to all the covalent bonds. Example : Molecular formula C5H12 Structural formulae : Step 1 CCCCC CCCC C C CCC C Step 2

Isomerism in alkenes 1. Isomerism occurs in alkenes due to the following reasons a) the position of the carbon-carbon double bond b) the different carbon chains in the molecule 2. The following are the guidelines for writing the structural formulae of the alkene isomers Step 1 : Write the straight chain and the branched chains Example : Molecular formula C5H10

Step 2 : Put in the carbon-carbon double bond at different positions.

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Step 3 : Add in the hydrogen atoms so that each carbon atom contains four covalent bonds.

Alkyl groups 1. An alkyl group has the general formula CnH2n+1 where n = 1,2,3 ... 2. The alkyl group is named by replacing the suffix -ane from the parent alkane with the suffix -yl as shown below Formula of alkyl group Name of alkyl group CH3Methyl C2H5- , CH3CH2-

Naming of branched-chain alkanes using the IUPAC system Step 1: Select the longest chain as the parent chain and name the parent chain. Step 2: Identify the alkyl group (side chain) that is joined to the parent chain, and name them. Step 3: Identify the position of the alkyl group by numbering the carbon atom in the parent chain. the numbering starts from the end of the parent chain that gives the lowest number to the carbon atom joined to the alkyl group. Step 4: Combine the name of the side chain with the name of the parent chain to obtain the name of the branched-chain alkane. Step 5: If the same alky group is present more than once as a side chain, the prefixes di, tri , and tetra are used to indicate 2,3 and 4 groups respectively. Exercises : Name the following alkanes Structural formula of alkanes CH3 CH3CCH3 CH3 CH3CH(CH3)CH(CH3)CH3 C2H5CH2CH(CH3)CH3 CH3CH2CHCH3 C2H5 IUPAC name of alkanes

Naming of branched-chain alkenes using the IUPAC system Step 1: Select the longest carbon chain with the double bond as the parent alkene. Step 2: Determine the position of the double bond by numbering the carbon atoms starting from the end of the carbon chain that gives the smallest number. Name the parent alkene. Step 3: Identify the alky group and its position Step 4: Name the branched-chain alkene

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Examples : Name the following compounds Structural formula of alkenes CCCCC CH3 CH3CCHCH3 CH2CH3 CH3CCHCH3

IUPAC name of alkenes

Exercise : An alkene Y has a relative molecular mass of 56. The alkene Y has the following composition by mass. Carbon 85.7% ; Hydrogen 14.3%. a) What is the molecular formula of Y b) Draw the structural formulae of the isomers of Y and name them

Alcohols 1. General formula CnH2n+1OH , where n = 1,2,3... 2. The functional group of alcohols is the hydroxyl group, (-OH) Naming of alcohols 1. Straight-chain alcohols are named by considering them as derivatives of alkanes. The lettere is replaced the suffix ol. 2. The position of the hydroxyl group are shown by numbering the carbon atoms from the end of the carbon chain which gives them smallest number. 3. For branched-chain alcohols, the position of the alkyl groups are also shown in the same manner Example : Name the alcohol CH3 CH3 CH3CH2 C CHCH3 OH Solution : Longest carbon chain Name of parent alcohol Position of OH group Positions of CH3 group Two methyl groups Name of alcohol : : : : : :

Isomerism in alcohols 1. Isomerism in alcohols in alcohols is caused by a) the position of the hydroxyl group b) branched-chain or straight chain 2. The following are the steps in writing the structural formulae of the isomers of alcohols. Step 1: Write down the straight-chain and all the possible branched-chain Step 2: Attach the hydroxyl group to different positions of the carbon atoms Step 3: Add single covalent bonds to each carbon atom and hydrogen atom to all the covalent bonds

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Example : Write the structural formulae of all the alcohols with the molecular formula C4H5OH , and name them. Industrial production of alcohols 1. Ethanol is produced industrially by two processes a) The hydration of ethene b) The fermentation of sugar or starch 2. Ethene is produced from petroleum by cracking(catalyst Al2O3) : C6H14

C4H10 +

C2H4

Hydration of ethene to ethanol 1. A mixture of ethene and steam is passed over the catalyst phosphoric acid, H3PO4 at 300oC and 65 atm. 2. The H atom and the OH group from the water (H2O) molecule are added across the double bond in the alkene molecule to form the alcohol Equation :

Preparation of ethanol in the laboratory by fermentation 1. When yeast is added to sugar, fermentation occurs. The enzyme, zymase, breaks down the glucose to ethanol and carbon dioxide. C6H12O6(aq) 2C2H5OH + 2CO2(aq) 2. Alcoholic drinks such as beer, wine and brandy are made industrially by fermentation of sugar. Physical Properties of ethanol 1. Ethanol is a colourless liquid. 2. Ethanol has a low boiling point (78oC) and is a volatile liquid. 3. Ethanol is very soluble in water despite being a covalent molecule. This is because the hydoxyl group dissolves readily in water. 4. The solubility of alcohols in water decreases as the molecular size increases because the effect of the hydrocarbon group becomes more prominent. Pentan-1-ol is insoluble in water. Chemical Properties of ethanol 1. Combustion of ethanol 1. Burns in excess of oxygen to produce carbon dioxide and water Equation : 2. Ethanol is a good fuel as it gives out a lot of energy when used. 2. Oxidation of ethanol 1. Ethanol is readily oxidised by acidified potassium manganate(VII) solution when heated. The alcohol is oxidised to carboxylic acid. The purple colour of manganate(VII) ions is decolourised and reduced to the manganese(II) ion, Mn2+. Equation : 2. Ethanol is also easily oxidised by acidified potassium dichromate(VI) solution when heated. The orange colour of the dichromate (VI) ions , Cr2O72- are reduced to the green chromium ions, Cr3+. 3. Dehydration of ethanol 1. The ethanol molecule can lose a water molecule(dehydration) to produce the ethene molecule and water when the following reagents and conditions are present.

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a) When ethanol vapour is passed over heated aluminium oxide. Equation : b) Ethanol vapour is passed over heated porcelain chips c) A mixture of ethanol and excess of concentration sulphuric acid is heated to 180oC d) A mixture of ethanol and concentration phosphoric acid is heated. Chemical Properties of other alcohols 1. Other alcohols have the same chemical properties as ethanol because of the presence of hydroxyl group. 2. Oxidation of alcohols produces the corresponding carboxylic acids. Examples : 3. Dehydration produces the corresponding alkenes Examples :

Uses of alcohols in everyday life Alcohols are used a) as fuels b) as solvents c) in medicine d) in making cosmetics 5) as a main component in alcoholic drinks

Carboxylic acids 1. General formula CnH2n+1COOH , where n = 0,1,2,3... 2. The functional group is the carboxyl group O - C OH Naming carboxylic acids 1. The acid is named by considering it as a derivative of alkane. The final letter e in the name of the corresponding alkane is dropped and replaced by the suffix oic followed by the word acid. 2. The carbon atom on the COOH group is always numbered as the first carbon atom. 3. Hence a number is not used to show the position of the COOH group. Examples Name of acid Structural formula Molecular formula Methanoic acid Ethanoic acid

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Preparation of ethanoic acid 1. Ethanol is oxidised to ethanoic acid by using oxidising agents like acidified potassium dichromate(VI) solution. 2. The colour of potassium dichromate(VI) solution changes from orange to green. Equation : Physical Properties of ethanoic acid 1. Ethanoic acid is colourless . 2. Pure ethanoic acid is known as glacial ethanoic acid because in cold weather, it freeze to form colourless crystals which look like ice. 3. The boiling point of ethanoic acid is 118oC. The boiling point increases on going down the group. 4. The first five members of the acids are very soluble in water because of the ionic group COOH. On going down the group, the solubility decreases as the carbon chain becomes longer.

Chemical Properties of ethanoic acid A) As a weak acid 1. Ethanoic acid is a weak acid because it ionises partially in water. Hence the concentration of hydrogen ion, H+ in the solution is low. 2. Like other acids, ethanoic acid will react with the following substances. However the rate of reaction is slower. a) Reaction with a base Reacts with bases to form salts and water. CH3COOH + NaOH CH3COOH + ZnO b) Reaction with metal carbonates Reacts to form salts, carbon dioxide, and water. CH3COOH + K2CO3 CH3COOH + CaCO3 c) Reactions with reactive metals Reacts to form salts and hydrogen. CH3COOH + Mg CH3COOH + Zn B) Esterification(Reaction between a carboxylic acid and an alcohol to produce ester and water) 1. Ethanoic acid reacts with ethanol in the presence of concentration sulphuric acid to produce the ester, ethyl ethanoate and water. 2. The concentration sulphuric acid acts as a catalyst and also a drying agent to remove the water that is produced. In this way the yield of the ester is increased. O CH3C-OH + H-OC2H5 Chemical Properties of other carboxylic acids

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Uses of carboxylic acid in everyday life 1. Methanoic acid and ethanoic acid are used to coagulate rubber latex. 2. Vinegar (4% ethanoic acid) is used as preservative and flavouring in food. 3. Ethanoic acid is used to make polyvinyl acetate that is used to make plastics and emulsion paints.
4. Benzoic acid , C6H5COOH is used to as food preservatives. 5. Butanoic acid is used to make esters that gives artificial flavourings in foods and in perfumes. Esters 1. General formula CnH2n+1COOCmH2m+1 , where n = 0,1,2,3... and m= 1,2,3..

2. Esters are formed by the reaction between carboxylic acids and alcohols (esterification) O R C OH + HOR
3. The functional group of ester is the carboxylate group, ............... 4. Esters and carboxylic acids have the same molecular formula CnH2nO2. 5. Hence esters and carboxylic acids that have the same number of carbon atoms per molecule are isomers. 6. Esters are also isomeric with other esters. Molecular formula Isomers Structural formula Name C3H6O2 HCOOC2H5 Ethyl methanoate CH3COOCH3 Methyl ethanoate CH3CH2COOH Propanoic acid C4H10O2

Naming of esters
1. The first part of the name of an ester is taken from the alkyl group of the alcohol. 2. The second part of the name is obtained by changing the -oic on the name of the acid to -oate. Reactants Esters Carboxylic acid Alcohol Name Formula HCOOH CH3OH Methanoic acid Methanol Ethanol acid Propanoic acid Methanol Ethanol

Preparation of ethyl ethanoate 1. Ethyl ethanoate can be prepared by heating a mixture of glacial ethanoic acid and absolute ethanol (pure). 2. A little amount of concentration sulphuric acid is added as a catalyst and also as a drying agent to increase the yield of ester by absorbing the water produced.

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3. When the reaction mixture is poured into a beaker of water the ester forms a fragrant layer on top of the water. 4. Larger quantities of esters can be prepared in the laboratory by refluxing a mixture of 30 cm3 of pure ethanol with 25 cm3 of glacial ethanoic acid in the presence of 5 cm3 of concentrated sulphuric acid. 5. A few chips of tiles are added to prevent bumping and ensure smooth boiling. 6. Pure ethyl ethanoate is obtained by distillation. Natural sources of esters 1. Simple esters are volatile and are responsible for the fragrant smell of flowers and fruits. 2. Larger molecular esters are found in vegetable oils and animal fats/oils. Uses of esters 1. Used as artificial food flavourings, perfumes. 2. Used as solvents for organic compounds. Pentyl ethanoate is used in nail polish. 3. Used to manufacture synthetic polymers like terylene. 4. Used as medicine. For example aspirin is an ester for relieving pains. Oils and Fats 1. Oils and fats are members of a group of organic compounds called lipids. 2. Oils and fats are found in animals and plants. 3. Fats are found in animals. 4. Fats is the highest source of energy for the human body. 5. Fats are important solvents for some hormones and vitamins A,D,E,K. Uses of oils and fats 1. Fats and oils are used for making soap. 2. The components of fats and oils are glycerol and fatty acids ( long-chain carboxylic acids containing 16 t0 18 carbon atoms). 3. Glycerol is used to make anti-freeze agents and also used in cosmetics. 4. Fats are solids whereas oils are liquids at room temperature. Saturated and Unsaturated fats 1. Saturated fats are naturally occurring esters formed from saturated carboxylic acids and glycerol. Saturated fat molecules do not contain any carbon-carbon double bonds. 2. Unsaturated fats are made up of molecules of esters containing at least one carbon-carbon double bond. 3. Unsaturated fats have lower boiling points due to the presence of double bonds. 4. Molecules with double bonds are packed less tightly and have lower melting points. 5. Unsaturated fats have very low cholesterol and can be hydrogenated. 6. Saturated fats have very high cholesterol content. CH2OH R1COOH CH2OH + R2COOH CH2OH R3COOH The effects of eating food high in fats 1. Saturated fats contain high percentage of cholesterol. 2. Cholesterol will deposit on the inner walls of arteries causing narrowing of the arteries. This will lead to a condition called arteriosclerosis. 3. Arteriosclerosis caused hardening of the blood vessels and results in hypertension. 4. Cholesterol combines with proteins to form lipoproteins. 5. Low density lipoproteins LDL) are bad cholesterols because they deposit on the walls of arteries.

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6. High density lipoproteins (HDL) are good cholesterols because they transport excess cholesterols from the tissue to the liver. The advantages of palm oil as compared to other vegetable oils 1. Used widely in the food industry as cooking oil, for making margarine, ice cream, biscuit cream. 2. Contains no cholesterol unsaturated fat. 3. Natural source of vitamins A and E and also a natural source of beta-carotene (anti-cancer properties) 4. Palm oil is resistant to oxidation and does not turn rancid easily. Natural Rubber 1. Found as latex of the rubber tree. 2. Its monomer is isoprene (2-methylbuta-1,3-diene) Polymerisation equation : Properties of natural rubber 1. Elasticity 1. Natural rubber consists of long chains of polymers coiled and intertwined together. 2. When stretched, the coiled chains lengthened and when the strain is removed, the rubber returns to its original shape. Hence rubber is elastic. 2. Oxidation 1. The double bonds in the polymers of natural rubber are easily oxidised by the air. 2. When oxidised, the rubber becomes hard and brittle. Hence it loses its elasticity. 3. Effect of heat 1.Natural rubber is non-resistant to heat and becomes sticky at high temperature. 4. Effect of solvent 1. Rubber does not dissolve in water and is impermeable to water. 2. Rubber is also resistant to attack by weak alkalis and acids. 3. Rubber is soluble in organic solvents like petrol, benzene and lubricating oils. Uses of natural rubber 1. Untreated natural rubber has many limitations and it has few practical uses. Can be used to make glues. 2. When treated, rubber is called vulcanised rubber. 3. Vulcanised rubber is more elastic, more resistant to heat and abrasion, and more resistant to oxidation. 4. Tyres usually contain 60% neutral rubber and 40% carbon and sulphur. Carbon black and sulphur are added to strengthen the rubber and to increase the resistance to corrosion and heat. 5. Vulcanised rubber are widely used as follows Property of rubber Uses 1. Resistant to abrasion Making vehicle tyres, conveyor belts 2. Flexibility Making rubber bands, hoses 3. Elasticity Making shock absorbers and balloons 4. Impermeable to fluids Making surgical gloves, raincoats 5. High electrical resistance Used as insulation for gloves, electric cables and equipment Coagulation of latex 1. Latex is a liquid containing rubber molecules, water and non-rubber materials (colloids). 2. The rubber molecules are contained in particles covered with a negatively-charged membrane of protein. 3. The negatively-charged membrane prevents the particles from coming close together.

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4. When a weak acid is added to the latex, the hydrogen ions from the acid will neutralise the negative charges on the membrane. 5. The neutral particles can come close together and collide, thus breaking the membrane. 6. The rubber polymers are released and combine to form layers of polymers that appears as lumps of rubber. The latex is said to coagulate. 7. The latex will also coagulate if left to stand for a few days because of the acids released by bacteria. 8. To prevent the coagulation of latex, an alkali such as ammonia is added to neutralise the acids produced by the bacteria. Vulcanisation of rubber 1. Untreated natural rubber is soft and less elastic than vulcanised rubber. 2. The polymers of untreated natural rubber slide over each other when the rubber is pulled. 3. Vulcanised rubber can be produced by a) heating natural rubber with sulphur at 140oC and zinc oxide as catalyst. b) mixing a solution of sulphur monochloride, S2Cl2 in methylbenzene with natural rubber. Activity : Comparing the properties of vulcanised and unvulcanised natural rubber A) Preparation of unvulcanised rubber and vulcanised ruber Apparatus : glass plate , beaker, tongs, razor blade, glass rod Materials : Sulphur monochloride in methylbenzene, rubber latex Procedure : 1. A small amount of latex is poured on a glass plate. 2. A glass rod is rolled over the latex to thin, flat layer of latex, 1mm thick. 3. The latex layer on the glass plate is left to coagulate for a few days. 4. The rubber produced is cut into two rectangular strips of equal size. 5. One of the strips is vulcanised by dipping it into a solution of sulphur monochloride in methylbenzene for 2 to 3 minutes. 6. The vulcanised strip is dried with filter papers. B) Comparing the properties of vulcanised rubber and unvulcanised rubber Apparatus : Retort stand/clamp, weight and thread, clips Materials : Vulcanised rubber strip, unvulcanised rubber strip Procedure : 1. The vulcanised rubber strip is hung using the clip. 2. The original length of the vulcanised rubber strip is measured and recorded. 3. A 15g weight is hung on the strip using another clip. 4. The increase in length of the strip is measured and recorded. 5. The weight is removed and the final length of the strip is measured and recorded. 6. Steps 1 to 5 are repeated by using the unvulcanised strip. Results Original Increase in Final length when Type of rubber length/cm Final length/cm length/cm weight is removed/cm Unvulvanised l0 l1 l1 l0 la ( la > l0) rubber Vulcanised rubber l0 l2 l2 l0 lb ( lb = l0 ) Discussion: 1. l2 l0 is less than l1 l0. This shows that the vulcanised rubber is harder than the unvulcanised rubber. 2. lb = l0 because the vulcanised will return to its original length after being stretched.

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Conclusion : Rubber rubber is harder, stronger and more elastic than unvulcanised rubber. Properties of vulcanised rubber diagram:

1. The sulphur atoms form cross-links between the long chains of polymers. 2. The sulphur cross-links prevent the chains of polymers from slipping over one another. Hence the strength of the rubber is increased. 3. When the force is released, the stretched piece of vulcanised rubber will return to its original length because the cross-links pull the polymer chains back to its original arrangement . 4. The presence of sulphur in vulcanised rubber increases the relative molecular mass of the rubber . The attractive forces between the larger rubber molecules will increase and the melting point of the rubber becomes higher. . Thus vulcanised rubber does not become soft and sticky. 5. Vulcanised rubber is more resistant to oxidation by the oxygen and ozone in the air because the number of carbon-carbon double bonds is reduced by the sulphur cross-links. 6. The strength and elasticity of vulcanised rubber will increase further if more sulphur cross-links are formed. STRUCTURED QUESTIONS 1. The figure below shows a flow chart for a series of changes on an alcohol R with the molecular formula C3H8O.

(a) Draw the set-up of apparatus to carry out step I in the laboratory. [2marks] (b) A mixture of alcohol R and acidified potassium dichromate(VI) solution is heated in step II (i) What can be observed in step II? [1 mark]

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(ii) Write the chemical equation for the reaction in step II. [1 mark] (c) Describe briefly how you can carry out step III in the laboratory [2 marks] (d) Draw the structural formula of compound Y. [1 mark] (e) (i) Name a catalyst that is used in step V. [1 mark] (ii) Describe briefly how you can carry out step V in the laboratory [2 marks] (iii) Give two differences in the physical properties between propyl propanoate and alcohol R. [2 marks] (f) Name the reagents used in step VI 2. The flow chart in the figure below shows the conversion of latex to vulcanised rubber through Step P and Q.

(a) Step P involves the coagulation of latex to form the unvulcanised rubber (i) Name a suitable reagent for step P [1 mark] (ii) Explain the changes that occur in step P [3 marks] (b) Draw the structural formula of the polymeric chain of unvulcanised rubber. Give its IUPAC name. [2 marks] (c) (i) Name process Q [1 mark] (ii) Describe briefly how unvulcanised rubber is converted into vulcanised rubber in step Q [1 mark] (d) List down three differences in the properties between unvulcanised rubber and vulcanised rubber [3 marks] (e) Describe the structural changes that occur when unvulcanised rubber is converted to vulcanised rubber in step Q [2 marks]

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