Organic Chemistry Specification Points Year 10 – Organic Chemistry Crude oil, hydrocarbons and alkanes Crude oil is a finite resource found in rocks made from the remains of an ancient biomass, mainly plankton that was buried in mud. Crude oil is a mixture of a very large number of compounds, mainly hydrocarbons (molecules made of hydrogen and carbon only). Most of the hydrocarbons in crude oil are hydrocarbons called alkanes. Alkanes are a homologous series with a general formula of CnH2n+2 The first four members of the alkanes are methane, ethane, propane and butane. Alkane molecules can be represented in the following forms: C2H6 or structural formula. Fractional distillation and petrochemicals Hydrocarbons in crude oil can be separated into fractions by fractional distillation by evaporating the oil and allowing it to condense at different temperatures. Fractions contain molecules with a similar number of carbon atoms. The fractions are processed to produce fuels and feedstock for the petrochemical industry. Many of the fuels on which we depend for our modern lifestyle, such as petrol, diesel oil, kerosene, heavy fuel oil and liquefied petroleum gases, are produced from crude oil. Many useful materials on which modern life depends are produced by the petrochemical industry, such as solvents, lubricants, polymers, detergents. Properties of hydrocarbons Some properties of hydrocarbons depend on the size of their molecules, including boiling point and viscosity which increase with increasing molecular size and flammability which decreases with increasing molecular size. These properties influence how hydrocarbons are used as fuels. During combustion, the carbon and hydrogen in the fuels are oxidised. The complete combustion of a hydrocarbon produces carbon dioxide and water and energy. Students should be able to write balanced equations for the complete combustion of hydrocarbons with a given formula. Knowledge of trends in properties of hydrocarbons is limited to boiling points, viscosity and flammability. Cracking and alkenes Hydrocarbons can be broken down (cracked) to produce smaller, more useful molecules. This process involves heating the hydrocarbons to vaporise them. The vapours are either passed over a hot catalyst or mixed with steam and heated to a very high temperature so that thermal decomposition reactions then occur. Be able to balance cracking equations. The products of cracking include alkanes and another type of hydrocarbon called alkenes. Alkenes are more reactive than alkanes and react with bromine water, turning it from orange to colourless. Cracking produces small molecules which have high demand for use in fuels. Alkenes are used to make polymers and as starting material to make many other chemicals. Structure and formulae of alkenes Alkenes are hydrocarbons with a double carbon to carbon bond. The general formula for the homologous series of alkenes is CnH2n Alkenes are unsaturated, they have two fewer hydrogen atoms than the comparable alkane The first 4 members of the homologous series are ethene, propene, butene and pentene. Alkene molecules can be represented in the following forms: C3H6 or structural formulae. Reactions of alkenes Alkenes are hydrocarbons with the functional group C=C. Alkenes react with oxygen in combustion reactions in the same way as other hydrocarbons, but they tend to burn in air with smoky flames because of incomplete combustion. Alkenes react with hydrogen, water and the halogens, by the addition of atoms across the carbon-carbon double bond so that the double bond becomes a single carbon-carbon bond. The addition of hydrogen to an alkene (unsaturated) takes place in the presence of a catalyst to produce the corresponding alkane (saturated). The addition of water to an alkene takes place by reaction with steam in the presence of a catalyst to produce an alcohol. Addition of a halogen to an alkene produces a saturated compound with two halogen atoms in the molecule, eg: ethene reacts with bromine to produce dibromoethane. Students should be able to draw fully displayed structural formulae of the first four members of the alkenes and the products of their addition reactions with hydrogen, water, chlorine, bromine and iodine. Polymers Polymers have very large molecules. The atoms in the polymer molecules are linked to other atoms by strong covalent bonds. The intermolecular forces between polymer molecules are relatively strong and so these substances are solids at room temperature. Addition polymerisation Alkenes can be used to make polymers such as poly(ethene) and poly(propene) by addition polymerisation. In addition polymerisation reactions, many small molecules (monomers) join together to form very large molecules (polymers). Students should be able to: • recognise addition polymers and monomers from diagrams in the forms shown and from the presence of the functional group C=C in the monomers • draw diagrams to represent the formation of a polymer from a given alkene monomer • relate the repeating unit to the monomer. Ceramics, polymers and composites Most of the glass we use is soda-lime glass, made by heating a mixture of sand, sodium carbonate and limestone. Borosilicate glass, made from sand and boron trioxide, melts at higher temperatures than soda-lime glass. Clay ceramics (pottery and bricks) are made by shaping wet clay and then heating in a furnace. The properties of polymers depend on what monomers they are made from and the conditions under which they are made. For example, low density (LD) and high density (HD) poly(ethene) are produced from ethene using different catalysts and reaction conditions. Thermosoftening polymers consist of individual, tangled polymer chains and melt when they are heated. Thermosetting polymers consist of polymer chains with cross-links between them and so they do not melt when they are heated. Most composites are made of two materials, a matrix or binder surrounding and binding together fibres or fragments of the other material, which is called the reinforcement. Examples of composites include wood, concrete and fibreglass. Some advanced composites are made using carbon fibres or carbon nanotubes instead of glass fibres. Students should be able to, given appropriate information: • compare quantitatively the physical properties of glass and clay ceramics, polymers, composites and metals • explain how the properties of materials are related to their uses and select appropriate materials. Independent Study suggestions 1. Look at the specification points above – use the textbook pages (244-277) or the revision guide pages (150-151) to make a few notes/spider diagram/revision cards 2. Have a go at the questions in the revision guide on pages 153-156 3. Watch the Fuse School short 3-4 minute explanation videos on any area you need extra help with: Coal, oil and gas: https://www.fuseschool.org/topics/59/contents/828 Fractional distillation: https://www.fuseschool.org/topics/59/contents/269 Uses of crude oil fractions: https://www.fuseschool.org/topics/59/contents/830 Functional groups: https://www.fuseschool.org/topics/59/contents/270 Formulae of organic compounds: https://www.fuseschool.org/topics/59/contents/268 Alkanes and Alkenes: https://www.fuseschool.org/topics/59/contents/233 Complete and incomplete combustion: https://www.fuseschool.org/topics/65/contents/330 Isomers: https://www.fuseschool.org/topics/59/contents/1198 Cracking: https://www.fuseschool.org/topics/59/contents/273 Alkenes and bromine water: https://www.fuseschool.org/topics/59/contents/829 Halogenation: https://www.fuseschool.org/topics/59/contents/883 Polymers: https://www.fuseschool.org/topics/59/contents/1000 Making polyethene: https://www.fuseschool.org/topics/59/contents/943 Polymers from chloroethene an propene https://www.fuseschool.org/topics/59/contents/279 Thermosetting polymers: https://www.fuseschool.org/topics/59/contents/972
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