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Unit 2 mod1 chem.

homologous series alkanes


Alkanes (Module 1) General formula CnH2n+2

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Alkanes are the simplest family of hydrocarbons - compounds containing carbon and hydrogen only. They only contain carbon-hydrogen bonds and carbon-carbon single bonds. The first three are: methane CH4, ethane C2H6 and propane C3H8. Alkanes are saturated meaning that they have only single bonds Alkanes undergo two types of reactions:- combustion and halogenation. They burn with a clean blue flame to form carbon dioxide and water e.g. C3H8 + 5O2 3CO2 + 4H2O They react with halogens in the presence of uv light to form a substituted alkane and a hydrogen halide e.g. CH4 (g) + 2O2 (g) CH3Cl (g) + HCl (g) Alkanes contain only carbon and hydrogen. Their electronegativities are very similar which means the C-H bond is essentially non-polar. Non-polar bonds do not attract either electrophiles or nucleophiles which are the species which undergo a reaction. Hence alkanes are generally unreactive. In the chlorination of methane, small amounts of ethane gas is always detected. This does not make any sense based on the simple series of substitutions. CH4 + Cl2 CH3Cl + HCl CH3Cl + Cl2 CH2Cl2 + HCl CH2Cl2 + Cl2 CHCl3 + HCl CHCl3 + Cl2 CCl4 + HCl It means the reaction occurs by some different means. A mechanism is proposed for the process. A mechanism is a proposed series of small steps from start to finish of a chemical reaction.

Unit 2 mod1 chem. homologous series alkanes

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Alkanes undergo free radical substitution mechanism. There are 3 stages. Initiation The reaction is initiated (started) by uv light breaking a chlorine molecule into free radicals (homolytic fission) Cl2 2Cl Propagation (this stage has 2 parts, the 1st part occurs with a molecule reacting with the free radicial and the 2nd part occurs with the free radical produced from the 1st part reacting with a halogen molecule regenerating a free radical for the process to start again) These are the reactions which keep the chain going. CH4 + Cl CH3 + HCl CH3 + Cl2 CH3Cl + Cl Termination These are the combination of any two free radicals 2Cl Cl2 CH3 + Cl CH3Cl CH3 + CH3 C2H6 (ethane gas)

The empirical and molecular formulae of hydrocarbons can be determined experimentally using combustion analysis and eudiometry. Combustion analysis involves burning a known mass of the hydrocarbon (or even if the compound is not a hydrocarbon) in air and finding the masses of the products. Sample calculation given below
95.6 mg of a compound containing carbon, hydrogen and oxygen l (molar mass = 156 g/mol) is burned in oxygen gas to give 269 mg CO2 and 110 mg H2O. What is the empirical formula of the compound? Ar C = 12.011, H = 1.008, O = 15.999 Solution: Mass of carbon present: 269 mg x (12.011 44.0098) = 73.4 mg Mass of hydrogen present : 110 mg x (2.016 18.0152) = 12.31 mg mass of oxygen: 95.6 - (73.4 + 12.31) = 9.88 mg C H O Mass(mg) 73.4 12.31 9.88 # of mol 6.11 12.21 0.617 ratio 9.9 19.8 1 E.F = C10H20O

Unit 2 mod1 chem. homologous series alkanes

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Eudiometry involves the use of Avogadros Law in using volumes to determine the molecular formula. The formula used in eudiometry is given below

NB unless you are told otherwise, assume excess oxygen is used. The reason for cooling is to remove any water vapour present and the products would just be a combination of carbon dioxide gas and excess oxygen gas. Potash/KOH and NaOH is used to absorb CO2 gas present, which allows one to determine the value of x. From Problem 15, after potash was used, volume decreased from 90ml to 70ml. This means that 20ml of CO2 present. Ratio of CxHy : CO2 = 10 : 20 = 1: 2 therefore x = 2 This means that 70ml is excess oxygen and if 100ml of oxygen was present for the reaction, then only 30 ml of oxygen was used. ratio CxHy : O2 = 10 : 30 = 1: 3 =3

if x = 2 then 2 + y = 3, therefore y = 4 and molecular formula is C2H4 4

Worksheet 1. Why are alkanes so unreactive? 2. By use of equations give a possible occurrence of when a molecule of octane is cracked ..

Unit 2 mod1 chem. homologous series alkanes


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7. 15 ml of a gaseous hydrocarbon was required for combustion in 357 ml of air ( 21% of O2 by volume ) . If the gaseous products occupied 327 ml (at rtp) what is the formula of the hydrocarbon.

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