Hydrocarbons and Fuels Alkanes, Alkenes, and Alkyne, Halogen derivatives, Aromatic Hydrocarbons,...
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- Hydrocarbons and Fuels Alkanes, Alkenes, and Alkyne, Halogen derivatives, Aromatic Hydrocarbons, Petrol, Alternative fuels,
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- Index Carbon chemistry introduction Alkanes and Alkenes Alkynes Halogen derivatives, CFCs Aromatic hydrocarbons Fuels
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- Organic Chemistry, the Chemistry of Carbon Originally chemical compounds were divided into 2 classes: Inorganic or Organic Organic compounds were derived from living things. It was believed that they contained a vital force and could not be made from inorganic compounds. Carbon has the ability to CATENATE, forming covalent bonds with its own atoms. CCHH
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- Organic Chemistry Organic chemistry is basically the study of compounds containing carbon (with the exclusion of oxides and carbonates) There are so many compounds containing carbon that a whole branch of chemistry is devoted to their study. Organic molecules may be as simple as methane, CH 4 or more complicated such as cholesterol HO
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- Alkanes and Alkenes Alkane general formula Alkene general formula C n H 2n+2 C n H 2n Structural formula Name No Cs Meth Eth Prop But Pent Hex Hept Oct 1234567812345678 CH 3 CH 2 CH 3 CH 3 (CH 2 ) 2 CH 3 Straight Chain CH 3 CH 2 CH 3 Branched Chains and unsaturated Condensed formulaMolecular formulaC3H7C3H7
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- Naming Compounds of Carbon 1.Identify the longest chain 2.Identify the branches and name them. 3.Number the carbon atoms on the longest chain, at the end giving the lowest numbers for the branches. 4.Write the branches in alphabetical order. 5.If there are more branches with the same name use di, tri etc Alkanes
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- Naming Compounds of Carbon 1.Identify the longest chain, that contains a double bond. 2.Identify the branches and name them. 3.Number the carbon atoms on the longest chain, starting from the end nearest the double bond. Pick the lowest number to describe the position of the double bond. 4.Write the branches in alphabetical order. 5.If there are more branches with the same name use di, tri etc Alkenes
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- Naming Organic Compounds H H C H H C CH 2 H C H H C H H C H H C CH 3 C H H CH 2 CH 3 1. Decide on the type of compound (ie. consider functional group) 2. Select the longest chain 3. Name the compound with the branched chains in alphabetical order. alkane 10 Cs decane 7-ethyl-3-methyldecane H H C H H C CH 2 H C H H C H H C H H C CH 3 C H H CH 2 CH 3
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- 1. Decide on the type of compound (ie. consider functional group) 2. Select the longest chain 4. Name the compound with the branched chains in ascending order. alkene 7 Cs heptene hept-2-ene 3. Number the C atoms so that the functional group has the lowest number 5,5-dimethylhept-2-ene H H C H C2H5C2H5 C H H C H CH 3 CC H =
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- 1. Decide on the type of compound (ie. consider functional group) 2. Select the longest chain 3. Name the compound with the branched chains and halogen in alphabetical order. halogen (chloroalkane) 5 Cs pentane 3-chloro-2,2-dimethylpentane H H C H CH 3 C H Cl H C H H CH 3 C H C H
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- STRUCTURAL ISOMERISM There are two types 1. Chain isomerism. Here the isomers have different arrangements of carbon atoms or different chains. For example there are two compounds with the molecular formula C 4 H 10 H H C H H H H C H HC H H C H H C H H C CH 3 H H H C butane2-methylpropane Here, you can see that 2-methylpropane has a side chain.
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- 2. Position Isomerism. Here the isomers have the same carbon skeleton and functional group but the position of the functional group is different. H H C H H H H C Cl HC H H C H H H C H HC 1-chloropropane2-chloropropane H H C H H H H C OH HC H H C H H H C H HC propan-1-olpropan-2-ol
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- Reaction of Alkenes Reaction with Hydrogen, hydrogenation, an addition reaction Reaction with halogens, + H-H Propene Propane 1,2 dibromopropane colourless + Br-Br Orange/red
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- Reaction with Hydrogen Halides + H-I 2 -iodopropane 1 -iodopropane or Normally the H from the halide attaches to the C which already has the most hydrogens.
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- Alkyne family C n H 2n-2 C2H2C2H2 Addition reactions with H 2 similar to alkenes. but two stages are possible Ethene CaC 2 + 2 H 2 O Ca(OH) 2 + C 2 H 2 Ni Catalyst 150 o C 1st 2nd CCHH CCHH CCHH + + H2H2 H2H2 Ethene Ethane HH
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- Halogen Derivatives Halogenalkanes and Halogenalkenes CHCl 3 CCl 4 CH 3 CCl 3 CCl 2 =CCl 2 CH 2 =CHClCF 2 =CF 2 2-bromo-2-chloro-1,1,1-trifluorethane Halothane CCl 2 F 2 Lava lamps, non-polar alkanes and chloroalkanes mixed with polar water. CCl 2 H 2 Chloroform Freon Correcting fluid Gortex, Teflon Solvent for grease Vinyl chloride Paint Stripper Degreasing agent
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- Halogen Derivatives, CFCs All CFCs are very unreactive, are not flammable and not toxic. They are used as flame retardants. CCl 3 F CCl 2 F 2 Chlorofluorocabons CFCs e.g. 1,1,1,2-tetrafluoroethane is used as a refrigerant. Used as a blowing agent to make expanded foam Recently Hydrofluorocarbons have replaced some CFCs. The first refrigerant, and in aerosols.
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- Ozone destruction O 3 CFCs are very stable, lasting for 100 years in the atmosphere. So over time, CFCs can reach the stratosphere. Here, UV radiation attacks the CFCs forming free radicals ( ). Free radicals react with O 3, the reaction is complex, but one Cl free radical can break down 1 million O 3 molecules. ClO + OCl + O 2 Chlorofluorocabons CFCs CCl 3 F CCl 2 F+ Cl U.V.light Cl + O 3 ClO + O 2
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- Aromatic Hydrocarbons Aromatic carbon molecules contain the benzene ring. Benzene F.A. Kekule proposed the original structure as a result of a dream. C6H6C6H6 Aliphatic carbon molecules contain the linear chains of carbon ring. Aromatic carbon molecules containing the benzene ring and aliphatic chains are called Arenes. The first structures are unstable and the electrons delocalise to form a much more stable structure.
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- Aromatic Properties CH 3 CH=CH 2 The benzene ring does not contain 3 double bonds, and so does not take part easily in addition reactions. It is insoluble in water, being non-polar. It burns with a smoky flame as carbon is produced. Aromatic compounds are used in dyes, herbicides, insecticides fungicides, Methylbenzene (toluene) Phenylethene (styrene) C 6 H 5 CH 2 CH 1,2 - dimethylbenzene 1,3 - dimethylbenzene
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- Aromatic compounds COOH OH Cl CHCCl 3 Poly-aromatic hydrocarbons PAH DDT dichlorodiphenyltrichloroethane COOCH 3 Aspirin 2-ethanoyloxybenzenecarboxcyclic acid NHCOCH 3 Paracetamol 4-hydroxyphenylethanamide
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- Petrol Long chain Hydrocarbons tend to burn unevenly in a car engine, causing knocking. Branched chained hydrocarbons burn more evenly, so prevent knocking. By products from the combustion of petrol are CO, CO 2, NO x and unburned Hydrocarbons The alkane 2,2,4,-trimethylpentane has good antiknock properties This also has a high octane rating, 100. Straight chain hydrocarbons have a lower octane rating, heptane has an octane number of 0. Benzene is 106. Unleaded petrol in UK has octane rating of 95. Petrol is a blend of different hydrocarbons and this can change depending on the season. In the winter you would need a petrol which was more volatile. Companies change their blend 3 or 4 times a year. CC H H H CH 3 C H H H C H H C H
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- Petrol Reforming, this is the process by which straight-chain alkanes undergo a chemical change to change them into new, smoother burning compounds. High temperatures, pressures and a catalyst are used. Branched-alkanes, cycloalkanes and aromatic compounds are produced. Hydrocracking, this takes place at high temperatures in the presence of hydrogen. Long straight chain hydrocarbons are changed into small branched chain and straight chain alkanes.
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- Alternative Fuels, biofuels Biogas Methane, produced by anaerobic respiration Ethanol Produced by fermentation, octane rating of 111 Methanol A liquid, made from steam and methane. Octane rating of 114, also clean burning. Toxic and corrosive Hydrogen economy The dream fuel, but needs electricity to make it. Fuel Cells 2x more efficient than the internal combustion engine. Requires a source of hydrogen and oxygen.
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- Did you know? CFCs where replaced by HFCs which do not degrade the ozone layer. However, they are greenhouse gases 1200x more powerful than CO 2. A fridge contains 0.67kg of HFCs, equivalent to 800 kg of CO 2. For this reason, some fridges now use HCs, such as butane and propane. These are only 3 to 4x as powerful a green house gas as CO 2.
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- Did you know? Methane is 23x more powerful a greenhouse gas as CO 2. Sewage methane can replace the use of natural gas for the generation of electrical power. So why does burning biogas give a negative value?