Alkanes: Formulae, Reactions & Structure

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www.igexams.comAlkanes: Formulae,Reactions & StructureQuestion Paper 1LevelInternational A LevelSubjectChemistryExam BoardEdexcelTopicThe Core Principles of ChemistrySub TopicAlkanes: Formulae, Reactions & StructureQuestion Paper 1BookletTime Allowed:59 minutesScore:/49Percentage:/100Grade Boundaries:A* 85%A777.5%BCDEU70%62.5%57.5%45% 45%

www.igexams.com1 The following molecules are alkenes.PQR(a) Which molecule has a geometric isomer?S(1)A PB QC RD S(b) Which molecule would produce 2-bromohexane as the major product onaddition of hydrogen bromide?(1)A PB QC RD S(c) Which molecule has 14 hydrogen atoms?(1)A PB QC RD S(Total for Question 1 3 marks)

www.igexams.com2 What is the systematic name for the following molecule?CH3CH3 CHC2H5CH2 CCH3C2H5A 2,4-diethyl-2-methylpentaneB 2,4-diethyl-4-methylpentaneC 3,3,5-trimethylheptaneD 3,5,5-trimethylheptane(Total for Question 2 1 mark)3 Which of the following is a step in the propagation stage of the chlorination of methane?A Cl2 o Cl. Cl.B CH3. Cl. o CH3ClC CH3. Cl2 o CH3Cl Cl.D CH4 Cl. o CH3Cl H.(Total for Question 3 1 mark)4 How many structural isomers have the molecular formula C6H14?A FourB FiveC SixD Seven(Total for Question 4 1 mark)

www.igexams.com5 (a) Which of the following represents the equation for the reaction between ethaneand chlorine in the presence of UV radiation?(1)A C2H6 Cl2 o C2H4Cl2 H2B C2H6 Cl2 o C2H5Cl HClC C2H6 Cl2 o 2CH3ClD C2H6 2Cl2 o 2CH3Cl 2HCl(b) The UV radiation initially causes the formation of(1)–A Cl ions.B Cl ions.C ClƔ free radicals.D C2H5Ɣ free radicals.(c) Once it has started, the reaction can proceed for a time without UV light because(1)A a chain reaction is occurring.B initiation is occurring.C a substitution reaction is occurring.D termination steps cannot occur without UV light.(Total for Question 5 3 marks)6 Which of the following is the systematic name for the hydrocarbon shown below?A 5-ethyl-4-methylhexaneB 2-ethyl-3-methylhexaneC 4,5-dimethylheptaneD 3,4-dimethylheptane(Total for Question 6 1 mark)

www.igexams.com7 Alkanes react with halogens in the presence of ultraviolet (UV) light.(a) Write the equation for the overall reaction of bromine with methane to formbromomethane. State symbols are not required.(1)(b) Propane reacts with chlorine to produce C3H7Cl. There are two possible isomerswith this molecular formula.Draw the skeletal formulae of these two isomers and give their systematic names.Name: . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .(4)Name: . . . . . . . .(c) Ethane reacts with chlorine in UV light by a free radical substitution mechanisminvolving a number of steps.(i) Explain why ethane does not react with electrophiles.(1). . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .(ii) Explain why ethane undergoes substitution and not addition reactions.(1). . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

www.igexams.com(iii) The first step of the reaction of chlorine with ethane in UV light involveshomolytic fission.Write the equation for this fission and state the name of this reaction step.Curly half-arrows are not required.(2)Equation:Name of reaction step . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .(iv) The ethyl free radical is an intermediate in the propagation stage of the reaction.Draw the dot-and-cross diagram of this free radical.Use dots ( ) for the hydrogen electrons, crosses (x) for the electrons of one ofthe carbon atoms and asterisks (*) for the electrons of the other carbon atom.Show only outer shell electrons.(v) What change to the reaction mixture of ethane and chlorine would increasethe production of polychlorinated alkanes such as 1,1-dichloroethane and1,2-dichloroethane?(2)(1). . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .(Total for Question 7 12 marks)

www.igexams.com8 The reaction of liquid bromine is a standard test for alkenes.(a) (i) Complete the equation for the reaction of cyclohexene with liquid bromine,using a skeletal formula.(1) Br2 (ii) What colour change would you see when this reaction occurs?From . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .(1)to . . . . . . . . . .(b) Gaseous but-1-ene is another alkene that readily reacts with liquid bromine.Using molecular formulae, the equation for the reaction isC4H8 Br2 C4H8Br2(i) Using the bond enthalpy values in the table, calculate the enthalpy change forthis reaction.BondBond enthalpy/kJ mol–1CH413CC347C C612CBr290BrBr193(2)

www.igexams.com(ii) Give one reason why the value calculated for the reaction in part (b)(i) usingbond enthalpies is different from the true value.Do not consider experimental error, mean bond enthalpy values ornon-standard conditions.(1). . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .(iii) Using appropriate curly arrows, write the mechanism of the reaction betweenbut-1-ene and bromine.(iv) Identify, by name or by displayed formula, the product formed whenbromine water is added to but-1-ene.(3)(1). . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .(Total for Question 8 9 marks)

www.igexams.com9 Compound X has the molecular formula C5H12.(a) Draw the displayed formulae of the three structural isomers of C5H12.(2)(b) C5H12 reacts with chlorine to form a mixture of products.(i) Classify the type and mechanism of this reaction.(2). . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .(ii) Write the equations for the two propagation steps for this mechanism. Use themolecular formula, C5H12, in your first equation. Curly arrows are not required.(2)(iii) Write the equation for one termination step for this mechanism. Curly arrowsare not required.(1)

www.igexams.com(c) An experiment was carried out to determine the enthalpy change of combustionof compound X, C5H12.100.0 g of water was heated by burning 0.144 g of compound X.The temperature rise of the water was 14.5 C.(i) Calculate the energy transferred, in kJ, in this experiment.Use the equationheat energy produced (J) mass of water 4.18 temperature change(1)energy transferred . . . . . . . . . . . . . . . . . . . . . kJ(ii) Calculate the number of moles of compound X used in this experiment.(1)moles of X . . . . . . . . . . . . . . . . . . . . . . . . . . . .(iii) Calculate the enthalpy change of combustion of compound X. Include a signand units in your answer.(2)enthalpy change of combustion . . . . . . . . . . . . . . . . . . . . . . . . . . . .

www.igexams.com(iv) The Data Book values for the enthalpy changes of combustion of the threestructural isomers with the formula C5H12 are:–3509.1 kJ mol–1–3503.4 kJ mol–1–3492.5 kJ mol–1The experimental value calculated in (c)(iii) is very different from these values.Give two reasons, other than heat loss, for this large difference.(2). . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .(v) Explain why it is not possible to deduce which of the isomers is compound Xby comparing this experimental value and the Data Book values.(1). . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

www.igexams.com*(d) Complete the Hess cycle and use it to calculate the enthalpy change ofcombustion of C5H12 from the following data.Show all of your working.Standard enthalpy change of formation of C5H12(l)–173.2 kJ mol–1Standard enthalpy change of combustion of H2(g)–285.8 kJ mol–1Standard enthalpy change of combustion of carbon(s, graphite)–393.5 kJ mol–1(4)5CO2(g) 6H2O(l)C5H12(l) 8O2(g). . .(Total for Question 9 18 marks)

6 Which of the following is the systematic name for the hydrocarbon shown below? A 5-ethyl-4-methylhexane B 2-ethyl-3-methylhexane C 4,5-dimethylheptane D 3,4-dimethylheptane (Total for Question

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