SPM Chemistry Form 5 Terminology and Concepts: Carbon Compounds 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 (Carbon-Carbon) 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 Alkene Alkynes Arenes CnH2n CnHn CnH2n-6 Functional group n = 1, 2, 3, n = 2, 3, 4, n = 2, 3, 4, n = 6, 7, 8, n = 1, 2, 3, n = 0, 1, 2 Carbon-carbon single bond -CCCarbon-carbon double bond -C=CCarbon-carbon triple bond -C=C-C=Cdelocalised / free to move around the ring Hydroxyl group - OH Carboxyl group - COOH Carboxylate group - COO -

Alcohol Carboxylic Acids Esters

CnH2n+1OH CnH2n+1COOH

CnH2n+1COOCmH2m+1 n = 0, 1, 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, alkenes, aromatic hydrocarbons and sulphur compound. These compounds can be separated by using fractional distillation.

< 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

Berry Quiz: How many known carbon compounds there are in the world now? Estimated to be around 10 million carbon compounds known. However, theoretically the number could be way larger. (Source: Wikipedia) 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 Prefix DiTriTetra-

5 6

PentaHexa-

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 o

Root name methethpropbutpenthexheptoctnandec-

The longest continuous (straight chain) carbon chain is selected. 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 Molecular formula of alkane CH4 C2H6

Propane Butane Pentane Hexane Heptane Octane Nonane Decane

C3H8 C4H10 C5H12 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 Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane Condensed structural formula of alkane CH4 CH3CH3 CH3CH2CH3 CH3CH2CH2CH3 CH3CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH2CH2CH2CH3 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 Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Molecularformula RMM CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 16 30 44 58 72 86 100 114 128 Density(g cm-3) 0.63 0.66 0.68 0.70 0.72 Physical state at 25C Gas Gas Gas Gas Liquid Liquid Liquid Liquid Liquid

Decane

C10H22

142

0.73

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.

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 + 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 carbon-carbon double (C = C) bond. Name of alkene Ethene Propene Butene Pentene Hexene Heptene Octene Nonene Decene

Molecular formula of alkene C2H4 C3H6 C4H8 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

4. Physical properties of alkenes Name Ethene Propene Butene Pentene Hexene Heptene Octene Nonene Decene

Molecularformula RMM C2H4 C3H6 C4H8 C5H10 C6H12 C7H14 C8H16 C9H18 C10H20 28 42 56 70 84 98 112 126 140

Density(g cm-3) 0.0011 0.0018 0.0023 0.6430 0.6750 0.6980 0.7160 0.7310 0.7430

Physical state at 25C Gas Gas Gas Liquid Liquid Liquid Liquid Liquid Liquid

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. 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

Reactivity of alkenes Alkenes are more reactive (unsaturated hydrocarbon). Alkenes have carbon-carbon (C = C) double bonds which is more reactive than carboncarbon (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)

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 carbon-carbon 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 1bromopropane and 2-bromopropane). 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 carbon-carbon double bond in a chemical test. SPM Form 5 Terminology and Concepts: Carbon Compounds 1. Comparing (Similarities and Differences) Properties of Alkanes and Alkenes 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 (Substitution reaction) Alkenes Same with alkanes.

Physical Properties Physical state

Electrical conductivity. Boiling points and melting points Density

Same with alkanes. Same with alkanes.

Same with alkanes.

Solubility in water Chemical Properties

Same with alkanes. Alkenes (Addition reaction)

Reactivity Combustion

Unreactive Burn in air and produce yellow sooty flame.

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

Reactive Burn in air and produce yellow and sootier flame compare to alkanes. Decolourise brown bromine solution. Decolourise purple acidified potassium manganate(VII) solution.

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

Molecular formula CH4 C2H6 C3H8 C4H10 C5H12

Isomerism in alkenes Number of isomers - (no isomer) - (no isomer) 3 5 Structure name Ethene Propene But-1-eneBut-2-ene2methylpropene Pent-1-enePent-2-ene2methylbut-1-ene 3-methylbut-1-ene 2-methylbut-2-ene

Molecular formula C2H4 C3H6 C4H8 C5H10