SPM Form 5 Terminology and Concepts: Carbon Compounds 1.

. Comparing (Similarities and Differences) Properties of Alkanes and Alkenes Physical Properties Physical state Alkanes Physical state changes from gas to liquid when going down the series. Do not conduct electricity at any state. Low boiling points and melting points (number of carbon atoms per molecule increases). Low densities (number of carbon atom per molecule increases). Insoluble in water (soluble in organic solvent) Alkanes Alkenes

solution Reaction with No reaction. acidified potassium manganate(VII) solution 2. Isomerism

solution. Decolourise purple acidified potassium manganate(VII) solution.

Same with alkanes.

Isomerism phenomenon that two or more molecules are found to have the same molecular formula but different structural formulae. Isomerism in alkanes Molecular formula CH4 C2H6 C3H8 C4H10 C5H12 Number of Structure name isomers - (no isomer) Methane - (no isomer) Ethane - (no isomer) Propane 2 Butane2methylpropane 3 Pentane2methylbutane2,2dimethylpropane

Electrical conductivity.

Same with alkanes.

Boiling points and melting points

Same with alkanes.

Density

Same with alkanes.

Isomerism in alkenes Same with alkanes. Molecular formula C2H4 C3H6 C4H8 Number of isomers - (no isomer) - (no isomer) 3 Structure name Ethene Propene But-1-eneBut-2ene2methylpropene Pent-1-enePent-2ene2-methylbut-1ene 3-methylbut-1-ene 2-methylbut-2-ene SPM Chemistry Form 5 Terminology and Concepts: Carbon Compounds

Solubility in water

Chemical Properties

Alkenes

(Substitution (Addition reaction) reaction) Reactivity Unreactive Reactive Combustion Burn in air and Burn in air and produce produce yellow yellow sooty and sootier flame. flame compare to alkanes. Reaction with No reaction. Decolourise bromine brown bromine

C5H10

1. Organic compounds carbon containing compounds with covalent bonds. 2. Inorganic compounds non-living things and usually do not contain carbon but few carbon containing inorganic compounds such as CO2, CaCO3 and KCN. 3. Hydrocarbons organic compounds that contain hydrogen and carbon atom only. 4. Non-hydrocarbons organic compounds that contain other elements (oxygen, nitrogen, iodine, phosphorus) 5. Saturated hydrocarbons only single bonded (Carbon-Carbon) hydrocarbons. 6. Unsaturated hydrocarbons at least one double / triple bonded (CarbonCarbon) hydrocarbons. 7. Complete combustion organic compounds burn completely which form CO2 and H2O. Example: C2H5OH (l) + O2 (g) > 2CO2 (g) + 3H2O (l) 8. Incomplete combustion organic compounds burn with limited supply of O2 which form C (soot), CO, CO2 and H2O. Homologous Series Homologous series organic compounds with similar formulae and properties. It have the physical properties that change gradually as the number of carbon atoms in a molecule increases. Carbon General Formula Compounds Alkane CnH2n+2 Functional group n = Carbon1, carbon 2, single bond 3, - C C n = Carbon2, carbon 3, double

4, bond -C=CAlkynes CnHn n = Carbon2, carbon 3, triple bond 4, - C = C Arenes CnH2n-6 n= -C=C6, delocalised 7, / free to 8, move around the ring Alcohol CnH2n+1OH n = Hydroxyl 1, group 2, - OH 3, Carboxylic CnH2n+1COOH n = Carboxyl Acids 0, group 1, 2 - COOH Esters CnH2n+1COOCmH2m+1 n = Carboxylate 0, group 1, - COO 2, m= 1, 2, 3, Sources of Hydrocarbon: 1. Coal from the lush vegetation that grew in warm shallow coastal swamps or dead plants slowly become rock. Mainly contains of hydrocarbon and some sulphur and nitrogen. It is used to produce: fertiliser, nylon, explosives and plastics. 2. Natural gas from plants and animals and trapped between the layers of impervious rocks (on top of petroleum). Mainly contains of methane gas and other gas such as propane and butane. It is used for: cooking, vehicle and generate electrical power. 3. Petroleum from plants and animals and trapped between the layers of impervious rocks. It is a complex mixture of alkanes,

Alkene

CnH2n

alkenes, aromatic hydrocarbons and sulphur compound. These compounds can be separated by using fractional distillation.

Butanoic acid

C3H7COH

164

< 35C petroleum gas 35C 75C Petrol (gasoline) 75C 170C Naphtha 170C 230C Kerosene 230C 250C Diesel 250C 300C Lubricating oil 300C 350C Fuel oil > 350C Bitumen

SPM Form 5 Terminology and Concepts: Carbon Compounds

Non-Hydrocarbon Carboxylic Acids 1. General formula: CnH2n+1COOH

Solubility in water generally in carboxylic acid (the less than four carbon atoms) are very soluble in water and ionise partially to form weak . Density of carboxylic acid density of carboxylic acid increases due to the increases in the number of carbon atoms in a molecule. Boiling points all carboxylic acid in general have relatively high boiling points than the corresponding alkanes. This is due to the presence of carboxyl group in carboxylic acid. Smell carboxylic acid (< 10 carbon) are colourless and pungent smell. Carboxylic acid (>10 carbons) are waxlike solids.

Where n = 0, 1, 2, 3 (n = number of carbon)

5. Preparation of carboxylic acid

2. Carboxylic acids are non-hydrocarbons which contain carbon, hydrogen and oxygen atoms. 3. The functional group in alcohols is carboxyl group, COOH. Name of carboxylic acids Methanoic acid(Formic acid) Ethanoic acid(Acetic acid) Propanoic acid Butanoic acid Molecular formula of alcohol HCOOH CH3COOH C2H5COOH C3H7COH

Oxidation of an alcohol The oxidation of ethanol is used to prepare ethanoic acid. C2H5OH + 2[O] > CH3COOH + H2O Carried out by refluxing* ethanol with an oxidising agent [acidified potassium dichromate(VI) solution orange colour turns to green / acidified potassium manganate(VII) solution purple colour turns to colourless] * reflux = upright Liebig condense to prevent the loss of a volatile liquid by vaporisation.

4. Physical properties of carboxylic acid Name Methanoic acid(Formic acid) Ethanoic acid(Acetic acid) Propanoic acid 6. Chemical properties of carboxylic acid Molecularformula Boiling point (C) HCOOH 101 Acid properties Ethanoic acid is a weak monoprotic acid CH3COOH 118 that ionises partially in water (produce a low concentration of hydrogen ions). CH3COOH <> CH3COO- + H+ C2H5COOH 141

Ethanoic acid turns moist blue litmus paper red. Reaction with metals Ethanoic acid reacts with reactive metals (copper and metals below it in the reactivity series cannot react with ethanoic acid). (K, Na, Mg, Al, Zn, Fe, Sn, Pb, Cu, Hg, Au) 2CH3COOH + Zn > Zn(CH3COO)2 + H2 In this reaction, a colourless solution (zinc ethanoate) is formed. 2CH3COOH + Mg > Mg(CH3COO)2 + H2 In this reaction, a colourless solution (magnesium ethanoate) is formed. Reaction with bases acid neutralises alkalis (sodium hydroxide). CH3COOH + NaOH > CH3COONa + H2O In this reaction, a salt (sodium ethanoate) and water are formed. Reaction with carbonates Ethanoic acid reacts with metal carbonates (calcium carbonate, magnesium carbonate, zinc carbonate). 2CH3COOH + CaCO3 > Ca(CH3COO)2 + CO2 + H2O In this reaction, a salt (calcium ethanoate), carbon dioxide and water are formed. Reaction with alcohols (Esterification) Ethanoic acid reacts with alcohol (ethanol, propanol, butanol) CH3CO-OH + H-OC4H9 > CH3COOC4H9 + H2O (Concentrated H2SO4 is a catalyst) In this reaction, an ester (colourless sweet-smelling liquid) (butyl ethanoate) and water are formed.

Benzoic acid is used as food preservative. Butanoic acid is used to produce ester (artificial flavouring).

SPM Chemistry Form 5 Terminology and Concepts: Carbon Compounds (Part 2) A) IUPAC (International Union of Pure and Applied Chemistry) is used to name organic compound. Organic compound is divided into three portions which is Prefix + Root + Suffix. 1. Prefix name of the branch or side chain. General formula: CnH2n+1 Where n = 1, 2, 3, (n = number of carbon) Formula CH3 C2H5 C3H7 C4H9 C5H11 Branch or name of group methyl ethyl propyl butyl pentyl

2. Alkyl group signifies that it is not part of the main chain. 3. Two or more types of branches are present, name them in alphabetical order. Number of side chain 2 3 4 5 6 Prefix DiTriTetraPentaHexa-

7. Uses of Carboxylic Acid

Carboxylic acid (methanoic acid and ethanoic acid) is used to coagulate latex. Vinegar (dilute 4% of ethanoic acid) is used as preservative and flavouring. Ethanoic acid is used to make polyvinvyl acetate which is used to make plastics and emulsion paints.

4. More than one side chains are present, prefixes are used. 5. Root the parent hydrocarbon (denotes the longest carbon chain).

Number of carbon atoms 1 2 3 4 5 6 7 8 9 10

o

Root name methethpropbutpenthexheptoctnandec-

Hexane Heptane Octane Nonane Decane

C6H14 C7H16 C8H18 C9H20 C10H22

Molecular formula is a chemical formula that shows the actual number of atoms of each type of elements present in a molecule of the compound. Example: molecular formula of butane is C4H24+2 = C4H10 Name Condensed structural formula of alkane Methane CH4 Ethane CH3CH3 Propane CH3CH2CH3 Butane CH3CH2CH2CH3 Pentane CH3CH2CH2CH2CH3 Hexane CH3CH2CH2CH2CH2CH3 Heptane CH3CH2CH2CH2CH2CH2CH3 Octane CH3CH2CH2CH2CH2CH2CH2CH3 Nonane CH3CH2CH2CH2CH2CH2CH2CH2CH3 Decane CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3 Structural formula is a chemical formula that shows the atoms of elements are bonded (arrangement of atoms) together in a molecule by what types of bond. 3. Physical properties of alkanes Name Molecularformul RM Density( Physica a M g cm-3) l state at 25C Methan CH4 16 Gas e Ethane C2H6 30 Gas Propane C3H8 44 Gas Butane C4H10 58 Gas Pentane C5H12 72 0.63 Liquid Hexane C6H14 86 0.66 Liquid

The longest continuous (straight chain) carbon chain is selected. o Identify the number of carbon. 6. Suffix functional group. Homologous series Alkane Alkene Alcohol Carboxylic acid Ester Functional group -CC-C=C OH COOH COO Suffix -ane -ene -ol -oic -oate

7. Example: 4-methylhept-2-ene. 8. Prefix + Root + Suffix B) Family of Hydrocarbon Alkane 1. General formula: CnH2n+2 Where n = 1, 2, 3, (n = number of carbon) 2. Each carbon atom in alkanes is bonded to four other atoms by single covalent bonds. Alkanes are saturated hydrocarbon. Name of alkane Methane Ethane Propane Butane Pentane Molecular formula of alkane CH4 C2H6 C3H8 C4H10 C5H12

Heptan e Octane Nonane Decane

C7H16 C8H18 C9H20 C10H22

100 0.68 114 0.70 128 0.72 142 0.73

Liquid Liquid Liquid Liquid

Alkanes with more than 17 carbon atoms are solid.

Solubility in water all members in alkanes are insoluble in water but soluble in many organic solvent (benzene and ether). Density of alkane the density of water is higher than density of alkane. When going down the series, relative molecular mass of alkanes is higher due to the higher force of attraction between molecules and alkane molecules are packed closer together. Electrical conductivity all members in alkanes do not conduct electricity. Alkanes are covalent compounds and do not contain freely moving ions. Boiling and melting points all alkanes in general have low boiling points and melting points. Alkanes are held together by weak intermolecular forces.

+ 2H2OIncomplete combustion occurs when insufficient supply of oxygen CH4 + O2 > C + H2O 2CH4 + 3O2 > 2CO + 4H2O Substitution reaction of alkanes (Halogenation) Substitution reaction is one atom (or a group of atoms) in a molecule is replaced by another atom (or a group of atoms). Substitution reaction of alkanes take place in ultraviolet light. Example: Alkanes react with bromine vapour (or chlorine) in the presence of UV light. CH4 + Cl2 > HCl + CH3Cl (Chloromethane) CH3Cl + Cl2 > HCl + CH2Cl2 (Dichloromethane) CH2Cl2 + Cl2 > HCl + CHCl3 (Trichloromethane) CHCl3 + Cl2 > HCl + CCl4 (Tetrachloromethane) The rate of reaction between bromine and alkanes is slower than the rate of reaction between chlorine and alkanes.

SPM Chemistry Form 5 Terminology and Concepts: Carbon Compounds (Part 3) Family of Hydrocarbon Alkene 1. General formula: CnH2n Where n = 2, 3, 4 (n = number of carbon) 2. Alkenes are unsaturated hydrocarbons which contain one or more carbon-carbon (C = C) double bonds in molecules. 3. The functional group in alkenes is carboncarbon double (C = C) bond. Name of alkene Ethene Propene Butene Molecular formula of alkene C2H4 C3H6 C4H8

4. Chemical properties of alkanes

Reactivity of alkanes Alkanes are less reactive (saturated hydrocarbon). Alkanes have strong carbon-carbon (C C) bonds and carbon-hydrogen (C H) bonds. All are single bonds which require a lot of energy to break. Alkanes do not react with chemicals such as oxidizing agents, reducing agents, acids and alkalis. Combustion of alkanes Complete combustion of hydrocarbons CxHy + (x + y/4) O2 > xCO2 + y/2 H2O CH4 + 2O2 > CO2

Pentene Hexene Heptene Octene Nonene Decene

C5H10 C6H12 C7H14 C8H16 C9H18 C10H20

Molecular formula is a chemical formula that shows the actual number of atoms of each type of elements present in a molecule of the compound. Example: molecular formula of butene is C4H2x4 = C4H8

Alkenes are covalent compounds and do not contain freely moving ions. Boiling and melting points all alkenes in general have low boiling points and melting points. Alkenes are held together by weak attractive forces between molecules (intermolecular forces) van der Waals force. When going down the series, more energy is required to overcome the attraction. Hence, the boiling and melting points increases.

5. Chemical properties of alkenes

4. Physical properties of alkenes Name Molecularformul RM Density( Physica a M g cm-3) l state at 25C Ethene C2H4 28 0.0011 Gas Propen C3H6 42 0.0018 Gas e Butene C4H8 56 0.0023 Gas Penten C5H10 70 0.6430 Liquid e Hexene C6H12 84 0.6750 Liquid Hepten C7H14 98 0.6980 Liquid e Octene C8H16 112 0.7160 Liquid Nonene C9H18 126 0.7310 Liquid Decene C10H20 140 0.7430 Liquid

Reactivity of alkenes Alkenes are more reactive (unsaturated hydrocarbon). Alkenes have carbon-carbon (C = C) double bonds which is more reactive than carbon-carbon (C-C) single bonds. All the reaction occur at the double bonds. Combustion of alkenes Complete combustion of hydrocarbons (alkenes) CxHy + (x + y/4) O2 > xCO2 + y/2 H2O C2H4 + 3O2 > 2CO2 + 2H2O (Alkenes burn with sootier flames than alkanes. It is because the percentage of carbon in alkene molecules is higher than alkane molecules and alkenes burn plenty of oxygen to produce carbon dioxide and water) Incomplete combustion occurs when insufficient supply of oxygen C2H4 + O2 > 2C + 2H2O C2H4 + 2O2 > 2CO + 2H2O (The flame in the incomplete combustion of alkenes is more smoky than alkanes)

Solubility in water all members in alkenes are insoluble in water but soluble in many organic solvent (benzene and ether). Density of alkene the density of water is higher than density of alkene. When going down the series, relative molecular mass of alkenes is higher due to the higher force of attraction between molecules and alkene molecules are packed closer together. Electrical conductivity all members in alkenes do not conduct electricity.

Polymerisation reaction of alkenes Polymers are substances that many monomers are bonded together in a repeating sequence. Polymerisation is small alkene

molecules (monomers) are joined together to form a long chain (polymer). nCH2 = CH2 > -(- CH2 CH2 -)-n ethene (monomer)(unsaturated compound) > polyethene polymer (saturated compound) It must be carry out in high temperature and pressure. Addition of hydrogen (Hydrogenation) Addition reaction is atoms (or a group of atoms) are added to each carbon atom of a carbon-carbon multiple bond to a single bond. C2H4 + H2 > C2H6 (catalyst: nickel and condition: 200C) Example: margarine (produce from hydrogenation of vegetable oils). Addition of halogen (Halogenation) Halogenation is the addition of halogens to alkenes (no catalyst of ultraviolet light is needed). Alkene + Halogen > Dihaloalkane C2H4 + Br2 > C2H4Br2 In this reaction the brown colour of bromine decolourised (immediately) to produce a colourless organic liquid. Bromination is also used to identify an unsaturated (presence of a carboncarbon double bond) organic compound in a chemical test. Addition of hydrogen halides Hydrogen halides (HX) are hydrogen chlorine, hydrogen bromide, hydrogen iodide and etc. This reaction takes place rapidly in room temperature and without catalyst. CnH2n + HX > CnH2n+1X C2H4 + HBr > C2H5Br (Bromoethane) (There are two products for additional of hydrogen halide to propene. The products are 1-bromopropane and 2bromopropane). Addition of water (Hydration) Alkenes do not react with water under ordinary condition. It can react with a mixture of alkene and steam pass over a catalyst (Phosphoric acid, H3PO4). The product is an alcohol.

CnH2n + H2O > CnH2n+1OH C2H4 + H2O > C2H5OH Additional of acidified potassium manganate(VII), KMnO4 CnH2n + [O] + H2O > CnH2n(OH)2 C2H4 + [O] + H2O > C2H5(OH)2 The purple colour of KMnO4 solution decolourised immediately to produce colourless organic liquid. Also used to identify the presence of a carboncarbon double bond in a chemical test.

SPM Form 5 Terminology and Concepts: Carbon Compounds Part 4 1. Comparing (Similarities and Differences) Properties of Alkanes and Alkenes Physical Properties Physical state Alkanes Physical state changes from gas to liquid when going down the series. Do not conduct electricity at any state. Low boiling points and melting points (number of carbon atoms per molecule increases) Alkenes Same with alkanes.

Electrical conductivity .

Same with alkanes.

Boiling points and melting points

Same with alkanes.

Density

Solubility in water

Chemical Properties

. Low densities (number of carbon atom per molecule increases) . Insoluble in water (soluble in organic solvent) Alkanes (Substituti on reaction) Unreactiv e Burn in air and produce yellow sooty flame.

Isomerism in alkanes Same with alkanes. Molecula r formula CH4 C2H6 Same with alkanes. C3H8 C4H10 Alkenes (Addition reaction) Reactive Burn in air and produce yellow and sootier flame compare to alkanes. Decolourise brown bromine solution. Decolourise purple acidified potassium manganate( VII) solution. Isomerism in alkenes Molecular formula C2H4 C3H6 C4H8 Number of isomers - (no isomer) - (no isomer) 3 Structure name C5H12 Numbe r of isomers - (no isomer) - (no isomer) - (no isomer) 2 3 Structure name

Methane Ethane Propane Butane2methylpropane Pentane2methylbutane2,2 dimethylpropane

Reactivity Combustion

Ethene Propene But-1-eneBut2-ene2methylpropene Pent-1enePent-2ene2methylbut-1ene 3-methylbut-1ene 2-methylbut-2ene

Reaction with bromine solution Reaction with acidified potassium manganate( VII) solution

No reaction.

C5H10

No reaction.

2. Isomerism Isomerism phenomenon that two or more molecules are found to have the same molecular formula but different structural formulae.

SPM Form 5 Terminology and Concepts: Carbon Compounds (Part 5)

Non-Hydrocarbon Alcohol 1. General formula: CnH2n-1OH

5. Chemical properties of alcohol

Where n = 1, 2, 3 (n = number of carbon)

2. Alcohols are non-hydrocarbons which contain carbon, hydrogen and oxygen atoms. 3. The functional group in alcohols is hydroxyl group, OH. Name of alcohol Molecular formula of alcohol Methanol CH3OH Ethanol C2H3OH Propanol / Propan-1-ol C3H5OH Butanol / Butan-1-ol C4H7OH Pentanol / Pentan-1-ol C5H9OH Hexanol / Hexan-1-ol C6H11OH Heptanol / Heptan-1-ol C7H13OH Octanol / Octan-1-ol C8H15OH Nonanol / Nonan-1-ol C9H17OH Decanol / Decan-1-ol C10H19OH 4. Physical properties of alcohol Name Molecular Melting Boiling formula point point (C) (C) Methanol CH3OH -97 65 Ethanol C2H3OH -117 78 Propanol C3H5OH -127 97 Butanol C4H7OH -90 118 Pentanol C5H9OH -79 138

Physical state at 25C Liquid Liquid Liquid Liquid Liquid

Solubility in water all members in alcohol are very soluble in water (miscible with water). Volatility all alcohols are highly volatile. Colour and Smell alcohols are colourless liquid and have sharp smell. Boiling and melting points all alcohols in general have low boiling points (78C).

Combustion of alcohol Complete combustion of alcohol. C2H5OH + 3O2 > 2CO2 + 3H2O (Alcohol burns with clean blue flames. Alcohol burns plenty of oxygen to produce carbon dioxide and water. This reaction releases a lot of heat. Therefore, it is a clean fuel as it does not pollute the air.) Other example: 2C3H7OH + 9O2 > 6CO2 + 8H2O Oxidation of ethanol In the laboratory, two common oxidising agents are used for the oxidation of ethanol which are acidified potassium dichromate(VI) solution (orange to green) and acidified potassium manganate(VII) solution (purple to colourless). C2H5OH + 2[O] > CH3COOH + H2O Ethanol oxidised to ethanoic acid (a member of the homologous series of carboxylic acids will be discussed in Part 6). Other example: C3H7OH + 2[O] > C2H5COOH + H2O Removal of water (Dehydration) Alcohol can change to alkene by removal of water molecules (dehydration). It results in the formation of a C=C double bond. CnH2n+1OH > CnH2n + H2O C2H5OH > C2H4 + H2O Two methods are being used to carry out a dehydration in the laboratory. a) Ethanol vapour is passed over a heated catalyst such as aluminium oxide, unglazed porcelain chips, pumice stone or porous pot. b) Ethanol is heated under reflux at 180C with excess concentrated sulphuric acid, H2SO4. Other example: C3H7OH > C3H6 + H2O

6. Uses of Alcohol

Alcohol as a solvent (cosmetics, toiletries, thinners, varnishes, perfumes). Alcohol as a fuel (fuel for racing car, clean fuel, alternative fuel).

Alcohol as a source of chemicals (polymer, explosives, vinegar, fiber). Alcohol as a source of medical product (antiseptics for skin disinfection, rubbing alcohol).

7. Misuse and Abuse

Depressant drug Alcoholic drinks Addictive drug

SPM Form 5 Terminology and Concepts: Carbon Compounds Part 6 Non-Hydrocarbon Carboxylic Acids 1. General formula: CnH2n+1COOH

Solubility in water generally in carboxylic acid (the less than four carbon atoms) are very soluble in water and ionise partially to form weak . Density of carboxylic acid density of carboxylic acid increases due to the increases in the number of carbon atoms in a molecule. Boiling points all carboxylic acid in general have relatively high boiling points than the corresponding alkanes. This is due to the presence of carboxyl group in carboxylic acid. Smell carboxylic acid (< 10 carbon) are colourless and pungent smell. Carboxylic acid (>10 carbons) are waxlike solids.

5. Preparation of carboxylic acid

Where n = 0, 1, 2, 3 (n = number of carbon)

2. Carboxylic acids are non-hydrocarbons which contain carbon, hydrogen and oxygen atoms. 3. The functional group in alcohols is carboxyl group, COOH. Name of carboxylic acids Methanoic acid(Formic acid) Ethanoic acid(Acetic acid) Propanoic acid Butanoic acid Molecular formula of alcohol HCOOH CH3COOH C2H5COOH C3H7COH

Oxidation of an alcohol The oxidation of ethanol is used to prepare ethanoic acid. C2H5OH + 2[O] > CH3COOH + H2O Carried out by refluxing* ethanol with an oxidising agent [acidified potassium dichromate(VI) solution orange colour turns to green / acidified potassium manganate(VII) solution purple colour turns to colourless] * reflux = upright Liebig condense to prevent the loss of a volatile liquid by vaporisation.

6. Chemical properties of carboxylic acid

4. Physical properties of carboxylic acid Name Methanoic acid(Formic acid) Ethanoic acid(Acetic acid) Propanoic acid Butanoic acid Molecularformula Boiling point (C) HCOOH 101 CH3COOH C2H5COOH C3H7COH 118 141 164

Acid properties Ethanoic acid is a weak monoprotic acid that ionises partially in water (produce a low concentration of hydrogen ions). CH3COOH <> CH3COO- + H+ Ethanoic acid turns moist blue litmus paper red. Reaction with metals Ethanoic acid reacts with reactive metals (copper and metals below it in

the reactivity series cannot react with ethanoic acid). (K, Na, Mg, Al, Zn, Fe, Sn, Pb, Cu, Hg, Au) 2CH3COOH + Zn > Zn(CH3COO)2 + H2 In this reaction, a colourless solution (zinc ethanoate) is formed. 2CH3COOH + Mg > Mg(CH3COO)2 + H2 In this reaction, a colourless solution (magnesium ethanoate) is formed. Reaction with bases acid neutralises alkalis (sodium hydroxide). CH3COOH + NaOH > CH3COONa + H2O In this reaction, a salt (sodium ethanoate) and water are formed. Reaction with carbonates Ethanoic acid reacts with metal carbonates (calcium carbonate, magnesium carbonate, zinc carbonate). 2CH3COOH + CaCO3 > Ca(CH3COO)2 + CO2 + H2O In this reaction, a salt (calcium ethanoate), carbon dioxide and water are formed. Reaction with alcohols (Esterification) Ethanoic acid reacts with alcohol (ethanol, propanol, butanol) CH3CO-OH + H-OC4H9 > CH3COOC4H9 + H2O (Concentrated H2SO4 is a catalyst) In this reaction, an ester (colourless sweet-smelling liquid) (butyl ethanoate) and water are formed.

SPM Form 5 Terminology and Concepts: Carbon Compounds (Part 7) Non-Hydrocarbon Esters 1. General formula: CnH2n+1COOCmH2m+1 Where n = 0, 1, 2, 3 and m = 1, 2, 3 (n and m = number of carbon) RCOOR where R and R represented the same or different alkyl groups. 2. Esters are non-hydrocarbons which contain carbon, hydrogen and oxygen atoms. 3. The functional group in ester is carboxylate group, COO -. CnH2n+1COOH + CmH2m+1OH > CnH2n+1COOCmH2m+1 + H2O

First part: taken from the alcohol (alkyl group) Second part: taken from the carboxylic acid (-oic to -oate) Prepared from

7. Uses of Carboxylic Acid

Carboxylic acid (methanoic acid and ethanoic acid) is used to coagulate latex. Vinegar (dilute 4% of ethanoic acid) is used as preservative and flavouring. Ethanoic acid is used to make polyvinvyl acetate which is used to make plastics and emulsion paints. Benzoic acid is used as food preservative. Butanoic acid is used to produce ester (artificial flavouring).

Name of ester Molecular formula of ester Ethyl HCOOC2H5 methanoate Methyl CH3COOCH3 ethanoate Propyl CH3COOC3H7 ethanoate Ethyl C2H5COOC2H5 propanoate 4. Physical properties of ester Name 3-metylbutyl acetate Ethyl butanoate Octyl ethanoate Isoamyl isovalerate

Ethanol + Methanoic acid Methanol + Ethanoic acid Propanol + Ethanoic acid Ethanol + Propanoic acid

Odour Banana Pineapple Orange Apple

Simple esters are colourless liquid and are found in fruits and flowers.

Esters have sweet pleasant smell. Esters are covalent compounds. Esters are insoluble in water but soluble in organic solvent. Esters are less dense than water. Esters are neutral and cannot conduct electricity. The higher and more complex esters have higher boiling points and less volatile.

1. Fatrs are non-hydrocarbons which contain carbon, hydrogen and oxygen atoms. 2. Fats (lipids / triglycerides) are belonging to the group in ester. 3. Natural esters are formed from glycerol and fatty acids. Name Molecular formula of ester of fat Types of fatty acids Saturate d Saturate d

Natural sources:

Vegetable oils (palm oil) and liquids esters can be found in plants derived from glycerol and fatty acids. Fats are solid esters (milk fat) derived from glycerol and fatty acids. Waxes (beewax) are solid ester derived from long-chain fatty acids and longchain alcohols.

5. Uses of Esters

Preparation of cosmetics and perfumes (esters are volatile and have sweet smell). Synthetic esters used as food additives (artificial flavour). Natural esters serves as storage reserve of energy in living things. In plant, wax (esters) helps to prevent dehydration and attack of microorganisms. Esters used as solvents for glue and varnishes. Esters used to make plastics softer. Esters used to produce polyester (threads and synthetics fabrics) Esters used to produce soap and detergents.

Lauric CH3(CH2)10COOH acid* Palmi CH3(CH2)14COOH tic acid* Steari CH3(CH2)16COOH Saturate c d acid* Oleic CH3(CH2)7CH=CH(CH2)7COOH Unsatur oxide ated ** Linole CH3(CH2)4CH=CHCH2CH=CH(CH2) Unsatur ic ated 7COOH acid* ** Linole CH3CH2CH=CHCH2CH=CHCH2CH= Unsatur nic CH(CH2)7COOH ated acid* ** * Saturated: C-C single bonds ** Unsaturated (monounsaturated): C=C double bonds *** Unsaturated (polyunsaturated): C=C double bonds 4. Animal fats have higher percentage of saturated fatty acids than unsaturated fatty acids.

SPM Form 5 Terminology and Concepts: Carbon Compounds (Part 8 ) Non-Hydrocarbon Fats

5. Plant oils have higher percentage of unsaturated fatty acids than saturated fatty acids. 6. Physical properties of fats Saturated C-C single bonds single higher animals high solid Unsaturated C=C double bonds double lower plants low liquid

obesity raise the level of cholesterol deposition will cause block the flow of blood which lead to stroke and heart attack.

9. Palm oil

Types of fatty acids Bonding Melting point Sources Cholesterol State at room temperature

It is extracted from fresh oil palm fruits. Palm oil extracted from the pulp of the fruits.

Steps in extraction of palm oil: 1. sterilising (oil palm fruit) 2. stripping 3. digestion (crushing the husk and fruit and separate the oil by heating) 4. squeezed out the oil 5. extraction (separate the oil from water) 6. purification the oil (palm oil is treated with phosphoric acid and then steam is passed through to separate the acid) 7. vacuum Palm kernel oil extracted from the kernel or seed. Steps in extraction of palm oil: 1. 2. 3. 4. 5. sterilising (oil palm fruit) stripping crushing the husk and fruit extracting kernel oil purification (purify the oil from kernel)

Fats (animal) in general are solids at room temperature and acted as:

thermal insulator protective cushion to protect the vital organ provide energy and stored in body carry Vitamin A, D, E, K (insoluble in water) Example: butter, fish oil (liquid in room temperature) Fats (plant) are called oils. Oils are liquids at room temperature. Example: olive oil, peanut oil, palm oil and bran oil

7. Chemical properties of fats

Unsaturated fats can be converted into saturated fats by hydrogenation (additional reaction) in 200C and 4 atm in the presence of nickel catalyst. Example: production of margarine from sunflower oil of palm oil.

Goodness in palm oil:

8. Effect of fats Fatty food produce high energy but high consumption of fatty food will results:

higher proportion of unsaturated fats. easy to digest and absorb. rich in vitamin A (carotenoid) rich in vitamin E (tocophenols and tocotrienols) resist oxidation in high temperature.

SPM Form 5 Terminology and Concepts: Carbon Compounds (Part 9 Final)

Polymers 1. Polymer many small units (monomers) joining together to formed large molecule. 2. Polymer can be classified into two groups:

Reaction to form polymer: additional polymerisation (one of the double bond in isoprene becomes single bond)

6. Structure of rubber molecule

synthetic polymers / man-made polymers (polythene; PVC polyvinyl chloride; artificial silk; and polypropene) natural polymers (natural rubber; starch; cellulose; and proteins)

3. Natural polymer: Carbohydrates (polysaccharides) (starch, glycogen and cellulose)

Latex is colloid (35% rubber particles and 65% water). Rubber particle contains rubber molecules which are wrapped by a layer of negatively-charged protein membrane. Same charge of rubber molecules repels each other. This prevent rubber from coagulate.

7. Coagulation process of latex The process for the coagulation of latex is summarised as: 1. Acid (H+) can neutralise the negativelycharged protein membrane. Example of acid: formic acid, methanoic acid, suphuric acid and hydrochloric acid. 2. The rubber molecules will collide after the protein membrane is broken. 3. Rubber molecules (polymers) are set free 4. Rubber molecules combine with one another (coagulation). 8. Natural coagulation process of latex For the natural coagulation of latex: 1. Latex is exposed to air without adding acid (duration overnight). 2. Coagulation process occurs in slower pace due to the bacteria (microorganism) action which produce acid) 9. Prevent coagulation process of latex The following are latex coagulation prevention method:

General formula: Cx(H2O)y with the ratio of H:O = 2:1 Carbohydrates have cyclic structure. Monomer: glucose (C6H12H6) Reaction to form polymer: condensation reaction (- H2O)

4. Natural polymer: Protein (polypeptide)

Protein consists of carbon, hydrogen, oxygen and nitrogen (some have sulphur, phosphorus and other elements) Monomer: amino acids Amino acids have two functional group which are carboxyl group (-COOH) and amino group (-NH2) Reaction to form polymer: condensation reaction (- H2O)

5. Natural polymer: Natural rubber

Extracted from the latex of rubber tree (Hevea brasiliensis) which the tree originates from Brazil. A molecule of rubber contains 5000 isoprene units. Monomer: isoprene, C3H8 or 2methylbuta-1,3-diene.

1. Alkaline / Basic solution is added to the latex. Example: ammonia (NH3). 2. Positively-charged hydrogen ion / H+ produced by bacteria can be neutralised by negatively-charged hydroxide ion / OH- from ammonia solution. 10. Properties of natural rubber

This also reduces the number of carbon-carbon double bonds in rubber molecules. Therefore, vulcanised rubber is more resistant to oxygen, ozone, sunlight and other chemicals.

13. Comparison between the properties of vulcanised rubber and unvulcanised rubber Properties Vulcanised rubber Unvulcanised rubber Double Decreases More number of bonds (formation of double bonds sulphur crosslinks) Melting High (presence of Low point sulphur) Elasticity More elastic Less elastics (sulphur crosslinks prevents the polymer chain or rubber from slipping past. Strength Strong and hard Weak and soft and (depends on (polymer chain hardness degree of of rubber will vulcanisation) break when rubber is over stretched. Resistant to Resistant to heat Poor resistant to heat heat Oxidation Resistant to Easily oxidised by oxidation oxygen, UV light (reduction of (presence of number of double many double bonds per rubber bonds per molecule) rubber molecules) 14. R & D of rubber

elastic cannot withstand heat (become sticky and soft above 50C; decompose above 200C; hard and brittle cooled) easily oxidised (present of C=C) insoluble in water (due to the long hydrocarbon chains) soluble in organic solvent (propanone, benzene, petrol etc.)

11. Vulcanisation of rubber Vulcanisation process of hardening rubber and increases rubber elasticity by heating it with sulphur or sulphur compounds. Methods:

heating natural rubber with sulphur at 140C using zinc oxide as catalyst or dipping natural rubber in a solution of disulphur dichloride (S2Cl2) in methylbenzene.

12. Properties of vulcanisation of rubber

The sulphur atoms are added to double bonds in the natural rubber molecules to form disulphide linkages (-C-S-S-C-) / sulphur cross-links between the long polymer chains. Therefore, vulcanised rubber is more elastics and stronger. This increases the molecular size and the intermolecular forces of attraction between rubber molecules. Therefore, vulcanised rubber is more resistant to heat (does not become soft and sticky when hot).

RRIM Rubber Research Institute of Malaysia MRB Malaysian Rubber Board Rubber Technology Centre Various local higher institutions of learning