Name: Organic Chemistry. Alkanes, Alkenes, Alcohols. Date: Time: 1 hour 53 minutes. Total marks available: 113. Total marks achieved:

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1 Name: Organic Chemistry Alkanes, Alkenes, Alcohols Date: Time: 1 hour 53 minutes Total marks available: 113 Total marks achieved: 2011 to 2013

2 Q1. (a) Explain what is meant by the term isomerism. (2) (b) The displayed formula of heptane (C7H16) is Which one of the displayed formulae below does not represent an isomer of heptane? Place a cross ( ) in the box to indicate your answer.

3 (c) Heptane belongs to a homologous series of compounds called alkanes. The general formula of the alkanes is CnH2n+2 (i) Heptene belongs to a homologous series of compounds called alkenes. Give the general formula of the alkenes. (ii) Complete the following diagram to show the structural formula of heptene (C7H14) by inserting lines to represent the covalent bonds between the carbon atoms. (2)

4 (d) When heptene is added to bromine water, and the mixture is shaken, a reaction occurs. State the type of reaction and give the colour of the bromine water before and after the reaction with heptene. (3) Type of reaction Colour before Colour after (e) Explain, in terms of the bonds present, why heptane is described as saturated and heptene as unsaturated. (2) (Total for Question = 11 marks) Q2. The table shows the displayed formulae of three unsaturated hydrocarbons.

5 (a) Explain the meaning of the term hydrocarbon. (2) (b) Explain the meaning of the term unsaturated. (c) Compounds A, B and C belong to the same homologous series. One characteristic of the compounds in a homologous series is that they have the same general formula. (i) State the name of this homologous series. (ii) State the general formula of this homologous series. (iii) State two other characteristics of the compounds in a homologous series.

6 (2) (d) Compound C has several isomers. (i) What is the name of compound C? (ii) What is the molecular formula of compound C? (iii) Explain the meaning of the term isomers. (2) (iv) Draw the displayed formula of an isomer of compound C. (e) Bromine water can be used to distinguish compound A from ethane. (i) Complete the sentence to show the colour change when compound A is bubbled

7 through bromine water. Bromine water changes from orange to.... (ii) Complete the chemical equation for the reaction between compound A and bromine water. C2H4 + Br2... (Total for Question = 14 marks) Q3. There are two important ways to manufacture ethanol. Reaction 1 C2H4 + H2O C2H5OH Reaction 1 C6H12O6 2C2H5OH + 2CO2 (a) (i) Identify one raw material that could be used as the source of C6H12O6 (ii) Reaction 2 uses a catalyst called zymase, which is present in yeast. Identify the catalyst used in reaction 1. (iii) In both reactions it is important to control the temperature. State why the temperature in reaction 2 is kept below 35 C.

8 (b) A manufacturing company plans to build a factory to produce ethanol on a large scale. The factory will be near an oilfield. The ethanol will be used as a solvent for perfume. Suggest why the company should use reaction 1 rather than reaction 2. (3) (c) In the future, it may be necessary to convert the ethanol (produced by reaction 2) into ethene. Write the equation for this reaction and state the type of reaction that occurs. (2) Equation Type of reaction...

9 ... (Total for Question = 8 marks) Q4. Fractional distillation and cracking are important steps in processing crude oil. (a) Place ticks ( ) in the columns to show which statements apply to each step. You may place a tick in one column, in both columns or in neither column. The first one has been done for you. (5) (b) The formula CH3CH2CH2CH2CH3 represents one of the compounds in crude oil. (i) Give the molecular formula of this compound. (ii) Give the displayed formula of this compound. (iii) Give the empirical formula of this compound.

10 (iv) Give the name of this compound. (v) Give the general formula of the homologous series that contains this compound. (c) The products of the complete combustion of hydrocarbons are carbon dioxide and water. (i) Balance the equation to show the complete combustion of ethene (C2H4). (2) C2H4 +...O2...CO2 +...H2O (ii) Draw a dot and cross diagram to show the bonding in an ethene molecule. Show only the outer electrons in each atom. (2) (d) Ethanol can be manufactured by the hydration of ethene. The equation for this reaction is C2H4(g) + H2O(g) C2H5OH(g) (i) Identify the catalyst and state the temperature used in this process. (2) Catalyst Temperature (ii) A 20 mol sample of ethanol was produced using this reaction. Deduce the amount, in moles, of ethene needed and the volume, in dm3, that this amount of ethene would occupy at room temperature and pressure.

11 Assume that all of the ethene is converted into ethanol and that the molar volume of ethene is 24 dm3 at rtp. (3) Amount of ethene mol Volume of ethene Volume =... dm3 (Total for Question = 19 marks) Q5. Decane is a hydrocarbon found in crude oil. The diagram shows the structure of a decane molecule. (a) (i) Explain why decane is described as a hydrocarbon. (2) (ii) Give the molecular formula for decane. (b) Decane and ethene, C2H4, are produced during the cracking of eicosane, C20H42 Ethene is used to make poly(ethene).

12 (i) What is the name given to this type of polymerisation? (ii) Use the diagram to state two changes that occur during the formation of poly(ethene). (2) (c) Explain why cracking is an important process in the oil industry. (4)

13 (Total for Question = 10 marks) Q6. This is a recipe for making plum wine.

14 (a) Sugar contains sucrose, C12H22O11 When yeast is added, water reacts with sucrose to form glucose, C6H12O6 Write a chemical equation for this reaction.

15 (b) The glucose is then converted into ethanol by the yeast C6H12O6(aq) 2C2H5OH(aq) + 2CO2(g) (i) How would you know when the reaction has stopped? (ii) How could the solid yeast be removed from the mixture? (c) Ethanol can be converted into chloroethene, CH2 CHCl, in three stages. CH2 Stage 1 Ethanol is dehydrated to form ethene, CH2 Stage 2 Ethene is converted into 1,2-dichloroethane, CH2ClCH2Cl Stage 3 1,2-dichloroethane is converted into chloroethene and hydrogen chloride (i) Why is the reaction in Stage 1 described as dehydration? (ii) Identify the catalyst used in the reaction in Stage 1. (iii) Suggest the name or formula of the substance used to react with ethene in Stage 2. (iv) Write a chemical equation for the reaction in Stage 3.

16 (d) Chloroethene can be used to make the polymer poly(chloroethene), also known as PVC. The displayed formula for part of the PVC molecule is (i) Draw a displayed formula for a chloroethene molecule. (ii) Describe, in terms of structure and bonding, what happens when chloroethene molecules are converted into poly(chloroethene). (3) (Total for Question = 11 marks) Q7.

17 This information was taken from a label on a packet containing a pizza. (a) (i) Which type of fat contains a double carbon to carbon (C==C) bond? (ii) The colour of bromine water is orange. State the final colour of the mixture after bromine water is shaken with (2) an unsaturated fat.. a saturated fat.. (iii) What type of reaction takes place when bromine reacts with a compound containing a C==C bond? (b) In February 2005, some companies had to remove their pizzas from sale because the food colourings in them were found to contain the artificial dye called Sudan 1, which is known to cause cancer. The chromatogram shows how the dyes in the colourings were detected and identified.

18 (i) Which one of the food colourings, A, B, C or D, is made up of only one dye? (ii) Identify the food colourings that may have contained Sudan 1. (iii) Explain how the chromatogram shows that the five food colourings are different from each other. (Total for Question = 7 marks)

19 Q8. The table shows percentage by mass of the fractions obtained from a sample of crude oil and the percentage market demand for these fractions. (a) Why is the market demand for the gasoline fraction greater than that for the fuel oil fraction? (b) Cracking is used to make long-chain hydrocarbon molecules into shorter-chain hydrocarbon molecules. (i) Complete the equation to show the other hydrocarbon molecule formed when C20H42 is cracked. C20H42 C16H34 +. (ii) Give the name of a catalyst used in industry to crack long-chain hydrocarbons and state a temperature at which cracking is carried out. (2) Catalyst

20 Temperature (c) Ethene (C2H4) can be produced by cracking long-chain hydrocarbon molecules obtained from crude oil. The ethene produced can then be used to make ethanol. Ethanol can also be made by the fermentation of sugars. (i) Give two advantages of making ethanol from ethene, rather than by fermentation. (2) (ii) Suggest two reasons why ethanol is sometimes made by fermentation, rather than from ethene. (2) (Total for Question = 8 marks)

21 Q9. The table shows the structures of six organic compounds, A to F. (a) The letter of the compound in the table that is not shown as a displayed formula is... (b) (i) State what is meant by the term hydrocarbon, and give the letter of one compound in the table that is not a hydrocarbon. (3) Hydrocarbon Letter (ii) State what is meant by the term unsaturated, and give the letter of one compound in the table that is unsaturated. (2) Unsaturated......

22 Letter (iii) State what is meant by the term isomers, and give the letters of two compounds in the table that are isomers of each other. (3) Isomers Letters. and. (c) Some of the compounds in the table are members of the same homologous series. (i) One feature of a homologous series is that adjacent members have formulae that differ by CH2 State two other features of members of the same homologous series. (2) 1 2 (ii) Give the letters of two adjacent members of the same homologous series shown in the table. Letters. and. (d) (i) Compound G has the molecular formula C2H4Br2

23 It can be made from a compound in the table by a reaction that does not need UV light. Draw the displayed formula of compound G. (ii) Compound H reacts with bromine to form one of the compounds in the table. The reaction needs UV light. Draw the displayed formula of compound H. (Total for Question = 14 marks) Q10. These are the displayed formulae of six organic compounds. (a) Use the letters above to select (i) the compound that is not a hydrocarbon.

24 (ii) one compound with the empirical formula CH2 (iii) one compound that can form a polymer. (b) Describe a test that will distinguish between compounds Q and T, and state the observation made with compound T. (2) Test Observation with compound T (c) Draw the displayed formula of an alkene containing four carbon atoms. (d) Three of the compounds belong to the alkane homologous series. All the alkanes in this homologous series have the same general formula. (i) What is the general formula of the alkanes? (ii) State two other features of a homologous series. (2) 1

25 2 (e) The displayed formulae below represent isomers. Explain what isomers are. (2) (Total for Question = 11 marks) Q1. On the whole this question was well answered. In (a), most students knew that isomers had different displayed or structural formulae, but some lost the first mark stating they have the same chemical or general formula rather than the same molecular formula. Rather strangely, a number of students who answered (a) correctly failed to identify the structure in (b) that was not an isomer of heptane.

26 The general formula of the alkenes was well known and most students were able to accurately complete the displayed formula of heptene, although some placed the double bond between the second and third carbon atoms from the left, whilst others drew either all single or all double bonds. In (d), very few knew that the reaction was addition, but the colour change was usually well known, although once again clear or transparent was given instead of colourless. The most common error in (e) was to fail to state that in a saturated hydrocarbon all of the carbon-carbon bonds are single. Q2. Parts (a) and (b) of this question about hydrocarbons were generally well done, although some lost marks in (a) through referring to hydrocarbons as atoms, or containing a mixture of hydrogen and carbon. The main problem in part (c) was with (iii), where the usual errors of giving a trend in chemical properties or the same physical properties were seen. Also, this time some repeated the general formula answer given in the question, and with many quoting properties specific to alkenes, such as decolourising bromine water or having double bonds. There were many good attempts at part (d), although in (iii) there were references to general formula instead of molecular formula, and some confusion with isotopes, while in (iv) some pentavalent carbon atoms appeared. Most knew the final colour in (e)(i), but the formula in (e)(ii) was sometimes carelessly written. Careless writing of symbols and use of subscripts is normally penalised once in each paper, and this part was chosen for the purpose - this meant that answers such as C2H4BR2 and C2H4Br2 did not score. Q3. Some candidates scored highly in part (a), but there were many errors, including glucose (not a raw material) in (i), catalysts such as iron and vanadium oxide in (ii), and to prevent ethanol from boiling away in (iii). Part (b) was generally well answered, with few candidates failing to score at least one mark. Some of the points that did not score included the release of carbon dioxide, and the oil being used to provide heat rather than ethene. Part (c) was also well answered, with errors including the equation in reverse, and water appearing on both sides. Q4. Parts (a) and (b) were well answered, with the commonest answers being in (b)(iii) (where there seemed to be a reluctance to give the same answer as in (b)(i)), and with some ambiguous answers (such as puntane and bentane in (b)(iv)). The ethene diagram

27 in (c)(ii) was generally well done, with few errors seen, such as the wrong number of carbon and/or hydrogen atoms shown. Part (d) was well answered. Q5. The definition of a hydrocarbon was well known, with only a small minority failing to mention that only hydrogen and carbon are present. However, some candidates described a hydrocarbon as a mixture of hydrogen and carbon and others incorrectly referred to the hydrogen and carbon present as being molecules rather than atoms. The molecular formula of decane was almost always given correctly, with a few stating that there were twelve atoms of hydrogen present. Almost everyone knew that the type of polymerisation was addition but many could not completely describe how the polymer was formed. Most realised that the one of the bonds in the double bond breaks, although this was usually described less accurately as 'the double bond breaks', but few were then able to take the next step and state that the monomer molecules joined together to make a chain. In part (c), there was a lot of confusion between cracking and fractional distillation, with many describing the latter and the usefulness of the fractions obtained. Many answers lacked structure and contained much irrelevant information about, for example, how cracking is achieved. However, very few failed to score at least one or two marks and there were many fully correct descriptions of the importance of cracking. Q6. The equation for the reaction of sucrose with water should have been straightforward since the formulae of two of the three substances involved were given in the question, with only water omitted. However, some candidates still preferred to invent compounds and include them in the equation. Some who got all formulae correct then failed to correctly balance the equation. Many spotted in (b)(i) that the bubbling would stop to signify the end of the reaction. The need to remove the yeast by filtration was well understood, although a variety of unsuitable methods, including chromatography, were seen. Part (c) produced many good answers, although the most accurate description of dehydration as removing the elements of water was rarely seen. One of the three acceptable alternatives to the catalyst was given in most cases and many were able to deduce from the two given formulae that chlorine was required to convert ethene into 1,2-dichloroethane. The equation in (c)(iv) was well answered, although some candidates who, perhaps unwisely, decided to change the structural formulae into molecular formulae made mistakes such as C2H4Cl instead of C2H3Cl.

28 (d)(i) was usually answered by the better candidates with no alterations or corrections, but others, at the end of a lot of crossing out, ended up with the incorrect answer. Often extension lines or two chlorine atoms were included. In (d)(ii), most candidates scored some marks as they had the idea that the double bond was broken and that the monomers joined together, although there were quite a few answers which talked about 'free hands' and the like. Although analogies such as these are sometimes useful in visualising concepts in Chemistry, they are of little use in answers to examination questions. Fewer talked about a long chain being formed and that the polymer contained only single bonds. Q7. In (a), most recognised that unsaturated fats contain a carbon-to-carbon double bond, but a number of students still used 'clear' to describe a colourless solution, seemingly failing to appreciate that all solutions, regardless of colour, are clear. Although bromine water was described in the question as being orange, yellow and brown were not penalised. The number of students who knew that the reaction is an addition was lower than expected. Most students correctly identified the food colourings in (b)(i) and (ii), but confusion between colourings and dyes in part (ii) made some answers difficult to interpret. There was no need to analyse the differences between named colourings. Comments on height and/or solubility of the dyes were also not required as the overall patterns should have been compared. Q8. In (a), very few candidates mentioned that gasoline is in such a high demand because of the large number of cars in the world. Some candidates effectively repeated the question by stating that it was in such high demand because it had a lot of uses. In (b), the vast majority had no problem in recognising the second hydrocarbon in (i). The name of the catalyst and the operating temperature were less well known. There were the obvious confusions between this process and the others listed in the specification, hence iron was often quoted as the catalyst and a temperature of 450 C was sometimes given. In (c)(i), many candidates knew that this was a fast process and that the ethanol produced was pure. The fact that it was a continuous process was rarely mentioned. Some gave answers which were too vague e.g. 'more ethanol is produced', which did not score since the amount of ethanol produced depends on the amounts of starting materials taken: it is the yield that is relevant. There were many good answers to (c)(ii) with the most common responses being, 'it uses a renewable resource' and 'it takes place at low temperatures'. It is important for candidates to realise that references to cost in industrial processes must always be qualified with a reason.

29 Q9. This question on fundamental organic chemistry was well attempted by most students. Many scored full, or almost full, marks in part (b), with the commonest error being in (ii), where the meaning of "saturated" was sometimes given. In (b)(iii), there were many answers that referred to isomers having just "the same formula", which is not precise enough to score the mark. In (c), there are still many examples of physical properties being described as similar, rather than showing a trend. Part (d) proved more of a challenge, with many examples in (i) containing two bromines joined to the same carbon atom, while in (ii) many answers showed the correct formula of bromomethane or only one C and three H atoms. Q10. Parts (a) and (b) were generally well done, although hydrogen sometimes appeared instead of bromine in the test for unsaturation. Many attempts at the displayed formula in (c) were successful, although some did not have four carbon atoms and rather more had a pentavalent carbon. In (d), the general formula was often correct, although it was disappointing to see many carelessly written attempts (such as CnH2n+2). The features of a homologous series were often correct. In (e), although some alternative wordings are acceptable, candidates should be aware that "chemical formula" is not equivalent to "molecular formula". Q1.

30 Q2.

31

32 Q3.

33 Q4.

34 Q5.

35

36 Q6.

37

38 Q7.

39 Q8.

40 Q9.

41

42

43 Q10.

44 Powered by TCPDF (

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