Draw one possible structure for each of the species A to J, using Table 2 on the Data Sheet where appropriate.

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1 Each of the parts (a) to (e) below concerns a different pair of isomers. Draw one possible structure for each of the species A to J, using Table 2 on the Data Sheet where appropriate. (a) Compounds A and B have the molecular formula C 5 H 0 A decolourises bromine water but B does not. A B (2) (b) Compounds C and D have the molecular formula C 2 H 4 O 2 Each has an absorption in its infra-red spectrum at about 700 cm but only D has a broad absorption at 3350 cm C D (2) (c) Compounds E and F are esters with the molecular formula C 5 H 0 O 2 The proton n.m.r. spectrum of E consists of two singlets only whereas that of F consists of two quartets and two triplets. E F (2) Page of 92

2 (d) Compounds G and H have the molecular formula C 3 H 6 C l2 G shows optical activity but H does not. G H (2) (e) Compounds I and J have the molecular formula C 6 H 2 Each has an absorption in its infra-red spectrum at about 650 cm and neither shows geometrical isomerism. The proton n.m.r. spectrum of I consists of a singlet only whereas that of J consists of a singlet, a triplet and a quartet. I J (2) (Total 0 marks) 2 The alkanes form an homologous series of hydrocarbons. The first four straight-chain alkanes are shown below. methane CH 4 ethane CH 3 CH 3 propane CH 3 CH 2 CH 3 butane CH 3 CH 2 CH 2 CH 3 (a) (i) State what is meant by the term hydrocarbon. Give the general formula for the alkanes. Page 2 of 92

3 (iii) Give the molecular formula for hexane, the sixth member of the series. (3) (b) Each homologous series has its own general formula. State two other characteristics of an homologous series (2) (c) Branched-chain structural isomers are possible for alkanes which have more than three carbon atoms. (i) State what is meant by the term structural isomers. Name the two isomers of hexane shown below. Name... Name... Page 3 of 92

4 (iii) Give the structures of two other branched-chain isomers of hexane. Isomer 3 Isomer 4 (6) (d) A hydrocarbon, W, contains 92.3% carbon by mass. The relative molecular mass of W is 78.0 (i) Calculate the empirical formula of W. Calculate the molecular formula of W. (4) (Total 5 marks) 3 (a) Complete the mechanism below by drawing appropriate curly arrows. (3) Page 4 of 92

5 (b) Draw and name the geometrical E-Z isomers of pent-2-ene. Isomer Isomer 2 Name Name (2) (c) Pent--ene reacts with hydrogen bromide to produce 2-bromopentane as the major product. (i) Outline the mechanism for this reaction. Identify the minor product formed in this reaction. (iii) Explain why 2-bromopentane is the major product of this reaction. (7) (Total 2 marks) Page 5 of 92

6 4 The alkene 3-methylpent-2-ene (CH 3 CH=C(CH 3 )CH 2 CH 3 ) reacts with hydrogen bromide to form a mixture of 3-bromo-3-methylpentane and 2-bromo-3-methylpentane. (a) The alkene 3-methylpent-2-ene (CH 3 CH=C(CH 3 )CH 2 CH 3 ) exists as E and Z stereoisomers. Draw the structure of Z-3-methylpent-2-ene. () (b) Name and outline the mechanism for the formation of 3-bromo-3-methylpentane from this reaction of 3-methylpent-2-ene with hydrogen bromide. Explain why more 3-bromo-3-methylpentane is formed in this reaction than 2-bromo- 3-methylpentane (7) (Total 8 marks) Page 6 of 92

7 5 (a) (i) Name the process used to separate petroleum into fractions. Give the molecular formula for an alkane with nine carbon atoms (iii) Write an equation for the complete combustion of the alkane C H 24 (iv) Write an equation for the incomplete combustion of C H 24 to produce carbon and water only. (4) (b) Alkenes can be produced by cracking the naphtha fraction obtained from petroleum. (i) Write an equation for the thermal cracking of one molecule of C 0 H 22 to give one molecule of propene and one molecule of an alkane only. Draw the structure of the chain isomer of but--ene. (2) Page 7 of 92

8 (c) The alkanes and the alkenes are examples of homologous series of compounds. One feature of an homologous series is the gradual change in physical properties as the relative molecular mass increases. State two other general features of an homologous series of compounds. Feature Feature (2) (Total 8 marks) 6 The structure of cyclohexene is shown. Which of the following is the general formula of cyclic alkenes such as cyclohexene? A C n H 2n 4 B C n H 2n 2 C C n H 2n D C n H 2n+2 (Total mark) 7 Compound J, known as leaf alcohol, has the structural formula CH 3 CH 2 CH=CHCH 2 CH 2 OH and is produced in small quantities by many green plants. The E isomer of J is responsible for the smell of freshly cut grass. (a) Give the structure of the E isomer of J. () Page 8 of 92

9 (b) Give the skeletal formula of the organic product formed when J is dehydrated using concentrated sulfuric acid. () (c) Another structural isomer of J is shown below. Explain how the Cahn-Ingold-Prelog (CIP) priority rules can be used to deduce the full IUPAC name of this compound (6) Page 9 of 92

10 (d) The effect of gentle heat on maleic acid is shown below. A student predicted that the yield of this reaction would be greater than 80%. In an experiment,0.0 g of maleic acid were heated and 6.53 g of organic product were obtained. Is the student correct? Justify your answer with a calculation using these data (2) (Total 0 marks) 8 2-bromo-2-methylpentane is heated with potassium hydroxide dissolved in ethanol. Two structural isomers are formed. (a) State the meaning of the term structural isomers () Page 0 of 92

11 (b) Name and draw the mechanism for the formation of one of the isomers. Name of mechanism... Mechanism (5) (Total 6 marks) 9 Dodecane (C 2 H 26 ) is a hydrocarbon found in the naphtha fraction of crude oil. Dodecane can be used as a starting material to produce a wide variety of useful products. The scheme below shows how one such product, polymer Y, can be produced from dodecane. (a) Name the homologous series that both C 2 H 4 and C 4 H 8 belong to. Draw a functional group isomer of C 4 H 8 that does not belong to this homologous series. Name... Functional group isomer (2) Page of 92

12 (b) Identify compound X.... () (c) Name polymer Y.... () (d) Reaction is an example of thermal cracking and is carried out at a temperature of 750 C. State one other reaction condition needed.... () (e) Reaction 2 is exothermic. A typical compromise temperature of 200 C is used industrially for this reaction. Explain the effect of a change of temperature on both the position of equilibrium and the rate of reaction, and justify why a compromise temperature is used industrially (6) (Total marks) 0 Isooctane (C 8 H 8 ) is the common name for the branched-chain hydrocarbon that burns smoothly in car engines. The skeletal formula of isooctane is shown below. Page 2 of 92

13 (a) Give the IUPAC name for isooctane.... () (b) Deduce the number of peaks in the 3 C NMR spectrum of isooctane () (c) Isooctane can be formed, together with propene and ethene, in a reaction in which one molecule of an alkane that contains 20 carbon atoms is cracked. Using molecular formulas, write an equation for this reaction.... () (d) How do the products of the reaction in part (c) show that the reaction is an example of thermal cracking?... () (e) Deduce the number of monochloro isomers formed by isooctane. Draw the structure of the monochloro isomer that exists as a pair of optical isomers. Number of monochloro isomers... Structure (2) Page 3 of 92

14 (f) An isomer of isooctane reacts with chlorine to form only one monochloro compound. Draw the skeletal formula of this monochloro compound. () (g) A sample of a monochlorooctane is obtained from a comet. The chlorine in the monochlorooctane contains the isotopes 35 Cl and 37 Cl in the ratio.5 :.0 Calculate the M r of this monochlorooctane. M r =... (2) (h) Isooctane reacts with an excess of chlorine to form a mixture of chlorinated compounds. One of these compounds contains 24.6% carbon and 2.56% hydrogen by mass. Calculate the molecular formula of this compound. Molecular formula =... (3) (Total 2 marks) Page 4 of 92

15 How many isomers have the molecular formula C 5 H 2? A 2 B 3 C 4 D 5 (Total mark) 2 How many structural isomers have the molecular formula C 4 H 9 Br? A 2 B 3 C 4 D 5 (Total mark) 3 How many secondary amines have the molecular formula C 4 H N? A 2 B 3 C 4 D 5 (Total mark) 4 Central heating fuel, obtained by the fractional distillation of crude oil, contains saturated hydrocarbons with the molecular formula C 6 H 34 (a) Give the meaning of the terms saturated and hydrocarbon as applied to saturated hydrocarbons. Saturated Hydrocarbon (2) Page 5 of 92

16 (b) If the boiler for a central heating system is faulty, a poisonous gas may be produced during the combustion of C 6 H 34 Write an equation for the reaction that forms this poisonous gas and one other product only.... () (c) Explain why the sulfur compounds found in crude oil should be removed from the fractions before they are used for central heating fuel (2) (d) A hydrocarbon C 6 H 34 can be cracked to form C 8 H 8, ethene and propene. (i) Write an equation to show this cracking reaction. () Suggest one important substance manufactured on a large scale from propene. () (iii) Draw the displayed formula of the functional group isomer of propene. () Page 6 of 92

17 (e) There are many structural isomers with the molecular formula C 8 H 8 Draw the structure of 2,3,3-trimethylpentane. () (f) A compound C 8 H 8 reacts with chlorine to give several haloalkanes. Give the IUPAC name of the following haloalkane.... () (Total 0 marks) 5 Some oil-fired heaters use paraffin as a fuel. One of the compounds in paraffin is the straight-chain alkane, dodecane (C 2 H 26 ). (a) Give the name of the substance from which paraffin is obtained. State the name of the process used to obtain paraffin from this substance. Substance... Process... (2) (b) The combustion of dodecane produces several products. Write an equation for the incomplete combustion of dodecane to produce gaseous products only.... () Page 7 of 92

18 (c) Oxides of nitrogen are also produced during the combustion of paraffin in air. (i) Explain how these oxides of nitrogen are formed. (2) Write an equation to show how nitrogen monoxide in the air is converted into nitrogen dioxide. () (iii) Nitric acid (HNO 3 ) contributes to acidity in rainwater. Deduce an equation to show how nitrogen dioxide reacts with oxygen and water to form nitric acid. () (d) Dodecane (C 2 H 26 ) can be cracked to form other compounds. (i) Give the general formula for the homologous series that contains dodecane. () Write an equation for the cracking of one molecule of dodecane into equal amounts of two different molecules each containing the same number of carbon atoms. State the empirical formula of the straight-chain alkane that is formed. Name the catalyst used in this reaction. Equation... Empirical formula of alkane... Catalyst... (3) Page 8 of 92

19 (iii) Explain why the melting point of dodecane is higher than the melting point of the straight-chain alkane produced by cracking dodecane. (2) (e) Give the IUPAC name for the following compound and state the type of structural isomerism shown by this compound and dodecane. IUPAC name... Type of structural isomerism... (2) (f) Dodecane can be converted into halododecanes. Deduce the formula of a substance that could be reacted with dodecane to produce -chlorododecane and hydrogen chloride only.... () (Total 6 marks) Page 9 of 92

20 6 The following table gives the names and structures of some structural isomers with the molecular formula C 5 H 0. Name of isomer Structure Isomer pent-2-ene CH 3 CH = CHCH 2 CH 3 Isomer 2 cyclopentane Isomer 3 3-methylbut--ene (CH 3 ) 2 CHCH = CH 2 Isomer 4 2-methylbut-2-ene (CH 3 ) 2 C = CHCH 3 Isomer 5 2-methylbut--ene H 2 C = C(CH 3 )CH 2 CH 3 (a) Isomer exists as E and Z stereoisomers. (i) State the meaning of the term stereoisomers. (2) Draw the structure of the E stereoisomer of Isomer. () Page 20 of 92

21 (b) A chemical test can be used to distinguish between separate samples of Isomer and Isomer 2. Identify a suitable reagent for the test. State what you would observe with Isomer and with Isomer 2. Reagent... Observation with Isomer Observation with Isomer (3) (c) Use Table A on the Data Sheet when answering this question. Isomer 3 and Isomer 4 have similar structures. (i) State the infrared absorption range that shows that Isomer 3 and Isomer 4 contain the same functional group. () State one way that the infrared spectrum of Isomer 3 is different from the infrared spectrum of Isomer 4. () (d) Two alcohols are formed by the hydration of Isomer 4. Draw the displayed formula for the alcohol formed that is oxidised readily by acidified potassium dichromate(vi). () Page 2 of 92

22 (e) Isomer 4 reacts with hydrogen bromide to give two structurally isomeric bromoalkanes. (i) Name and outline a mechanism for the reaction of Isomer 4 with hydrogen bromide to give 2-bromo-2-methylbutane as the major product. (CH 3 ) 2 C = CHCH 3 + HBr (CH 3 ) 2 CBrCH 2 CH 3 Name of mechanism... Mechanism (5) The minor product in this reaction mixture is 2-bromo-3-methylbutane. Explain why this bromoalkane is formed as a minor product. (2) (f) Name and outline a mechanism for the following reaction to form Isomer 5. State the role of the hydroxide ion in this reaction. (CH 3 ) 2 CBrCH 2 CH 3 + KOH H 2 C = C(CH 3 )CH 2 CH 3 + KBr + H 2 O Name of mechanism... Mechanism Role of hydroxide ion... (5) (Total 2 marks) Page 22 of 92

23 7 This question is about some isomers of C 5 H 8 O 2 (a) Compound H is a cyclic ester that can be prepared as shown. On the structure of H, two of the carbon atoms are labelled. HOCH 2 CH 2 CH 2 CH 2 COCl + HCL H (i) Name and outline a mechanism for this reaction. Use Table C on the Data Sheet to give the 3 C n.m.r. δ value for the carbon atom labelled a and the δ value for the carbon atom labelled b. (7) Page 23 of 92

24 HOCH 2 CH 2 CH 2 CH 2 COCl can also react to form a polyester in a mechanism similar to that in part (i). Draw the repeating unit of the polyester and name the type of polymerisation involved. (2) (b) State how you could distinguish between compounds J and K by a simple test-tube reaction. State how you could distinguish between J and K by giving the number of peaks in the H n.m.r. spectrum of each compound. J K (5) Page 24 of 92

25 (c) Draw the structure of each of the following isomers of C 5 H 8 O 2 Label each structure you draw with the correct letter L, M, N, P or Q. L is methyl 2-methylpropenoate. M is an ester that shows E-Z stereoisomerism. N is a carboxylic acid with a branched carbon chain and does not show stereoisomerism. P is an optically active carboxylic acid. Q is a cyclic compound that contains a ketone group and has only two peaks in its H n.m.r. spectrum. (5) (Total 9 marks) 8 (a) The hydrocarbon but--ene (C 4 H 8 ) is a member of the homologous series of alkenes. But--ene has structural isomers. (i) State the meaning of the term structural isomers. (2) Give the IUPAC name of the position isomer of but--ene. () (iii) Give the IUPAC name of the chain isomer of but--ene. (iv) Draw the displayed formula of a functional group isomer of but--ene. () () Page 25 of 92

26 (b) But--ene burns in a limited supply of air to produce a solid and water only. (i) Write an equation for this reaction. () State one hazard associated with the solid product in part (b)(i). () (c) One mole of compound Y is cracked to produce two moles of ethene, one mole of but--ene and one mole of octane (C 8 H 8 ) only. (i) Deduce the molecular formula of Y. () Other than cracking, give one common use of Y. () (d) In cars fitted with catalytic converters, unburned octane reacts with nitrogen monoxide to form carbon dioxide, water and nitrogen only. (i) Write an equation for this reaction. () Identify a catalyst used in a catalytic converter. () (Total marks) 9 Compound X is shown below. It is a member of a homologous series of hydrocarbons. (a) (i) Deduce the general formula of the homologous series that contains X. () Name a process used to obtain a sample of X from a mixture containing other members of the same homologous series. () Page 26 of 92

27 (b) There are several isomers of X. (i) Give the IUPAC name of the position isomer of X. () Draw the structure of a functional group isomer of X. () (c) At high temperatures, one molecule of C 5 H 32 can be converted into two molecules of X and one molecule of another compound. (i) Write an equation for this reaction. () State the name of the process used to obtain a high yield of X from C 5 H 32 Give one reason why this process is used in industry. Name... Reason... (2) (iii) State why high temperatures are needed for this process. () (d) Compound X can be converted into compound Y. Compound Y is shown below. (i) Suggest the formula of a reagent that could be added to X in order to convert it into Y. () Page 27 of 92

28 Give one use of Y. () (iii) Write an equation to show the reaction of Y in a limited supply of air to produce a solid and water only. () (iv) When a sample of Y, contaminated with CH 3 SH, is burned completely in air, a toxic gas is formed. Identify this toxic gas and suggest a compound that could be used to remove the toxic gas from the products of combustion. Toxic gas... Compound used to remove toxic gas... (2) (v) Suggest the name of the process that occurs when the toxic gas in part (d)(iv) is removed. () (e) Explain why the boiling points of X and Y are similar (2) (Total 6 marks) 20 Hexane (C 6 H 4 ) is a member of the homologous series of alkanes. (a) (i) Name the raw material from which hexane is obtained. () Page 28 of 92

29 Name the process used to obtain hexane from this raw material. () (b) C 6 H 4 has structural isomers. (i) Deduce the number of structural isomers with molecular formula C 6 H 4 Write the number in this box. (Space for working) () State one type of structural isomerism shown by the isomers of C 6 H 4 () (c) One molecule of an alkane X can be cracked to form one molecule of hexane and two molecules of propene. (i) Deduce the molecular formula of X. () State the type of cracking that produces a high percentage of alkenes. State the conditions needed for this type of cracking. Type of cracking... Conditions... (2) (iii) Explain the main economic reason why alkanes are cracked. () Page 29 of 92

30 (d) Hexane can react with chlorine under certain conditions as shown in the following equation. C 6 H 4 + Cl 2 C 6 H 3 Cl + HCl (i) Both the products are hazardous. The organic product would be labelled flammable'. Suggest the most suitable hazard warning for the other product. () Calculate the percentage atom economy for the formation of C 6 H 3 Cl (M r = 20.5) in this reaction. () (e) A different chlorinated compound is shown below. Name this compound and state its empirical formula. Name... Empirical formula... (2) (Total 2 marks) 2 Pentane is a member of the alkane homologous series. (a) Give the general formula for the homologous series of alkanes.... () Page 30 of 92

31 (b) One of the structural isomers of pentane is 2,2-dimethylpropane. Draw the displayed formula of 2,2-dimethylpropane. State the type of structural isomerism shown.... (2) (c) A molecule of hydrocarbon Y can be thermally cracked to form one molecule of pentane and two molecules of ethene only. Deduce the molecular formula of Y. State why high temperatures are necessary for cracking reactions to occur. Give one reason why thermal cracking reactions are carried out in industry (Extra space) (3) Page 3 of 92

32 (d) Write an equation for the incomplete combustion of pentane to form a solid pollutant. Suggest why this solid pollutant is an environmental problem (Extra space) (2) (e) Pentane can react with chlorine as shown in the following equation. C 5 H 2 + Cl 2 C 5 H Cl + HCl Calculate the percentage atom economy for the formation of C 5 H Cl Deduce how many straight-chain isomers of C 5 H Cl could be formed (Extra space) (3) Page 32 of 92

33 (f) Consider the following compound. Name this compound. Deduce the empirical formula of this compound (2) (Total 3 marks) Page 33 of 92

34 22 The table below shows the structures of three isomers with the molecular formula C 5 H 0 O Isomer (E)-pent-3-en-2-ol Isomer 2 pentanal Isomer 3 (a) Complete the table by naming Isomer 3. () (b) State the type of structural isomerism shown by these three isomers.... () (c) The compound (Z)-pent-3-en-2-ol is a stereoisomer of (E)-pent-3-en-2-ol. (i) Draw the structure of (Z)-pent-3-en-2-ol. () Identify the feature of the double bond in (E)-pent-3-en-2-ol and that in (Z)-pent-3-en-2-ol that causes these two compounds to be stereoisomers. () Page 34 of 92

35 (d) A chemical test can be used to distinguish between separate samples of Isomer 2 and Isomer 3. Identify a suitable reagent for the test. State what you would observe with Isomer 2 and with Isomer 3. Test reagent... Observation with Isomer Observation with Isomer (3) (e) The following is the infrared spectrum of one of the isomers, 2 or 3. (i) Deduce which of the isomers (, 2 or 3) would give this infrared spectrum. You may find it helpful to refer to Table on the Data Sheet. () Page 35 of 92

36 Identify two features of the infrared spectrum that support your deduction. In each case, identify the functional group responsible. Feature and functional group... Feature 2 and functional group... (2) (Total 0 marks) 23 Octane is the eighth member of the alkane homologous series. (a) State two characteristics of a homologous series (2) (b) Name a process used to separate octane from a mixture containing several different alkanes () Page 36 of 92

37 (c) The structure shown below is one of several structural isomers of octane. Give the meaning of the term structural isomerism. Name this isomer and state its empirical formula (4) (d) Suggest why the branched chain isomer shown above has a lower boiling point than octane (2) (Total 9 marks) 24 Pent--ene is a member of the alkene homologous series. (a) Pent--ene can be separated from other alkenes. State the physical property of alkenes that allows them to be separated from a mixture by fractional distillation.... () Page 37 of 92

38 (b) (i) State the meaning of the term structural isomerism. (2) Name the branched chain isomer of pent--ene shown below. () (iii) Draw the structure of a functional group isomer of pent--ene. () (c) The cracking of one molecule of compound X produces pent--ene, ethene and butane in a :2: mol ratio. Deduce the molecular formula of X and state a use for the ethene formed. Molecular formula of X Use of ethene... (2) (Total 7 marks) Page 38 of 92

39 25 Hexane is a member of the homologous series of alkanes. (a) State two characteristics of a homologous series. Characteristic Characteristic (2) (b) (i) Hexane can be converted into 2,2-dichlorohexane. Draw the displayed formula of 2,2-dichlorohexane and deduce its empirical formula. Displayed formula Empirical formula... (2) Explain why 2,2-dichloro-3-methylpentane is a structural isomer of 2,2-dichlorohexane. (2) (c) A reaction of hexane with chlorine is shown by the equation below. C 6 H 4 + 2Cl 2 C 6 H 2 Cl 2 + 2HCl Calculate the percentage atom economy for the formation of C 6 H 2 Cl 2 in this reaction (2) Page 39 of 92

40 (d) The boiling points of some straight-chain alkanes are shown below. Alkane C 4 H 0 C 5 H 2 C 6 H 4 Boiling point / C (i) Explain the trend in these boiling points. (2) Name a process which can be used to separate C 5 H 2 from C 6 H 4 () (Total marks) 26 (a) Hexane (C 6 H 4 ) is a hydrocarbon which is a component of LPG (liquid petroleum gas), used as a fuel for heating. When burning fuels in boilers it is important to ensure complete combustion. (i) Give two reasons why boilers are designed to ensure complete combustion. Reason... Reason 2... Write an equation for the incomplete combustion of hexane. (iii) Suggest how an engineer or a chemist could demonstrate that the combustion of hexane in a faulty boiler was incomplete. (5) Page 40 of 92

41 (b) Branched chain alkanes are often preferred as fuels. Draw the structure of two branched chain isomers of hexane and name the first isomer. Isomer Isomer 2 Name of isomer... (3) (c) Hexane can be cracked in the presence of a catalyst to produce another hydrocarbon, Z, and methane. (i) Draw a possible structure for Z. Give a suitable catalyst for this reaction. (iii) Suggest why the product Z has more commercial value than hexane. (3) (d) The overall equation for the production of dichloromethane from methane and chlorine is shown below. CH 4 + 2Cl 2 CH 2 Cl 2 + 2HCl (i) Calculate the % atom economy for the formation of CH 2 Cl 2 in this reaction. Page 4 of 92

42 Give one reason why this atom economy of less than 00% is an important consideration for the commercial success of this process and predict how a chemical company would maximise profits from this process. (3) (Total 4 marks) 27 There are seven isomeric carbonyl compounds with the molecular formula C 5 H 0 O. The structures and names of some of these isomers are given below. Structure Name pentanal 2-methybutanal 2, 2-dimethypropanal pentan-2-one (a) (i) Complete the table. Page 42 of 92

43 Two other isomeric carbonyl compounds with the molecular formula C 5 H 0 O are not shown in the table. One is an aldehyde and one is a ketone. Draw the structure of each. isomeric aldehyde isomeric ketone (4) (b) Pentanal, CH 3 CH 2 CH 2 CH 2 CHO, can be oxidised to a carboxylic acid. (i) Write an equation for this reaction. Use [O] to represent the oxidising agent. Name the carboxylic acid formed in this reaction. (2) (c) Pentanal can be formed by the oxidation of an alcohol. (i) Identify this alcohol. State the class to which this alcohol belongs. (2) (Total 8 marks) Page 43 of 92

44 28 (a) The infra-red spectrum of compound A, C 3 H 6 O 2, is shown below. Identify the functional groups which cause the absorptions labelled X and Y. Using this information draw the structures of the three possible structural isomers for A. Label as A the structure which represents a pair of optical isomers. (6) (b) Draw the structures of the three branched-chain alkenes with molecular formula C 5 H 0 Draw the structures of the three dibromoalkanes, C 5 H 0 Br 2, formed when these three alkenes react with bromine. One of these dibromoalkanes has only three peaks in its proton n.m.r. spectrum. Deduce the integration ratio and the splitting patterns of these three peaks. (0) (Total 6 marks) 29 Which one of the following can exhibit both geometrical and optical isomerism? A (CH 3 ) 2 C=CHCH(CH 3 )CH 2 CH 3 B CH 3 CH 2 CH=CHCH(CH 3 )CH 2 CH 3 C (CH 3 ) 2 C=C(CH 2 CH 3 ) 2 D CH 3 CH 2 CH(CH 3 )CH(CH 3 )C=CH 2 (Total mark) Page 44 of 92

45 30 How many different alkenes are formed when 2-bromo-3-methylbutane reacts with ethanolic potassium hydroxide? A 2 B 3 C 4 D 5 (Total mark) 3 The table below gives some of the names and structures of isomers having the molecular formula C 4 H 9 Br Structure Name CH 3 CH 2 CH 2 CH 2 Br 2-bromo - 2-methypropane -bromo - 2-methypropane 2-methypropane Complete the table. (Total 2 marks) Page 45 of 92

46 32 (a) Name and outline a mechanism for the reaction of 2-bromo-2-methylpropane with ethanolic potassium hydroxide to form the alkene 2-methylpropene, (CH 3 ) 2 C=CH 2 Name of mechanism... Mechanism (4) (b) Two stereoisomers of but-2-ene are formed when 2-bromobutane reacts with ethanolic potassium hydroxide. (i) Explain what is meant by the term stereoisomers. Draw the structures and give the names of the two stereoisomers of but-2-ene. Stereoisomer Stereoisomer 2 Name... Name... (iii) Name this type of stereoisomerism. (5) (c) When 2-bromo-2-methylpropane reacts with aqueous potassium hydroxide, 2-methylpropan-2-ol is formed as shown by the following equation. State the role of the hydroxide ions in this reaction.... () Page 46 of 92

47 (d) Write an equation for the reaction that occurs when CH 3 CH 2 CH 2 CH 2 Br reacts with an excess of ammonia. Name the organic product of this reaction. Equation... Name of product... (3) (Total 3 marks) 33 Consider the following reaction in which an alkene is formed from a haloalkane. (a) Name the haloalkane used in this reaction.... () (b) Name and outline a mechanism for this reaction. Name of mechanism... Mechanism (4) Page 47 of 92

48 (c) Another alkene, which is a structural isomer of but-2-ene, is also formed during this reaction. (i) State what is meant by the term structural isomers. Draw the structure of this other alkene. (2) (Total 7 marks) 34 Some alcohols can be oxidised to form aldehydes, which can then be oxidised further to form carboxylic acids. Some alcohols can be oxidised to form ketones, which resist further oxidation. Other alcohols are resistant to oxidation. (a) (b) Draw the structures of the two straight-chain isomeric alcohols with molecular formula, C 4 H 0 O Draw the structures of the oxidation products obtained when the two alcohols from part (a) are oxidised separately by acidified potassium dichromate(vi). Write equations for any reactions which occur, using [O] to represent the oxidising agent. (2) (6) (c) Draw the structure and give the name of the alcohol with molecular formula C 4 H 0 O which is resistant to oxidation by acidified potassium dichromate(vi). (2) (Total 0 marks) Page 48 of 92

49 35 The compound cis-retinal is shown below. Which one of the labelled bonds leads to the prefix in the name? (Total mark) 36 Which one of the following is a pair of functional group isomers? A CH 3 COOCH 2 CH 3 and CH 3 CH 2 COOCH 3 B (CH 3 ) 2 CHCH(CH 3 ) 2 and (CH 3 ) 3 CCH 2 CH 3 C D CH 3 CH 2 OCH 3 and (CH 3 ) 2 CHOH ClCH 2 CH 2 CH=CH 2 and CH 3 CH=CHCH 2 Cl (Total mark) Page 49 of 92

50 Mark schemes (a) A any C 5 alkene B (b) C or CH 3 COOH or HCOOCH 3 D or HOCH 2 CHO (c) E F Page 50 of 92

51 (d) G H (e) I J NOT hex-3-ene [0] 2 (a) (i) Molecule/compound/consists/composed/made up of hydrogen and carbon only () C n H 2n+2 () (b) (iii) C 6 H 4 only () Do not credit structures alone or in addition. Chemically similar / react in same way / same chemistry Differ by CH 2 gradation in physical properties OR specified trend e.g. b.p. same functional group Any 2, 2 marks + Not same molecular formula 3 2 Page 5 of 92

52 (c) (i) Same molecular formula () NOT same Mr different structural formula / structures () (or atoms arranged in different way) NOT different spatial arrangements Only credit M2 if M correct 2-methylpentane () 2,2-dimethylbutane () (iii) OR correct condensed / structural formula Penalise sticks once Penalise absence of vertical bonds once penalise badly drawn bonds once (vertical between H atoms) 6 (d) (i) M % by mass of H = 7.7(0)% () M2 mol H = 7.70 / = 7.70 mol C = 92.3 / 2 = 7.69 () M3 (ratio : ) CH Credit variations for M2 e.g. 78 = 6 and = 6 Correct answer = 3 marks (CH has empirical mass of 3 and = 6 ) C 6 H 6 () Correct answer mark 4 [5] Page 52 of 92

53 3 (a) M curly arrow from lone pair on oxygen of hydroxide ion to H atom on C-H adjacent to C-Br M2 curly arrow from single bond of adjacent C-H to adjacent single bond C-C (only credit M2 if M is being attempted to correct H atom) M3 curly arrow from C-Br bond to side of Br atom (credit M3 independently) (b) Ml credit a correct structure for either geometrical E-Z isomer and its designation as either cis or trans. OR credit two correct geometrical E-Z isomer structures (ignore the names) OR credit two correct names for cis pent-2-ene and trans pent-2-ene (ignore the structures) M2 credit a second mark if all four parts of the required structures and names are correct. (credit linear structures) (insist on the alkyl groups being attached clearly by C-C bonds) (c) (i) Ml curly arrow from middle of C = C bond to H atom on H-Br (penalise M if partial negative charge or formal positive charge on H) (penalise Ml if pent-2-ene is used) M2 curly arrow from H-Br bond to side of Br atom M3 correct structure for correct secondary carbocation M4 curly arrow from lone pair on bromide ion to the positive carbon of carbocation, ensuring that bromide ion has a negative charge. (with the exception of pent-2-ene, if the wrong alkene is used, only penalise the structure M3) (penalise the use of two dots in addition to a covalent bond, once only) -bromopentane Page 53 of 92

54 (iii) Ml 2-bromopentane is formed via the secondary (or 2 ) carbocation OR -bromopentane is formed via the primary (or ) carbocation M2 a secondary carbocation is more stable than a primary carbocation - award this mark only if the quality of language justifies the award. (the argument must involve clear statements about carbocations) [2] 4 (a) Must show all 4 groups bonded to C=C Allow CH 3 for methyl group; allow C 2 H 5 for ethyl group Allow correct structure of the style Allow correct skeletal structure Page 54 of 92

55 (b) M electrophilic addition NB the arrows here are double-headed M2 M3 M4 M5 M6 must show an arrow from the double bond towards the H atom of the H-Br molecule must show the breaking of the H-Br bond is for the structure of the tertiary carbocation must show an arrow from the lone pair of electrons on the negatively charged bromide ion towards the positively charged atom (of either a secondary or) of a tertiary carbocation 3-bromo-3-methylpentane is formed from 3 y carbocation OR 2-bromo-3-methylpentane is formed from 2 y carbocation M7 3 y carbocation more stable than 2 y M2-M5 Penalise one mark from their total if half-headed arrows are used M2 Ignore partial negative charge on the double bond M3 Penalise incorrect partial charges on H-Br bond and penalise formal charges Penalise M4 if there is a bond drawn to the positive charge Penalise only once in any part of the mechanism for a line and two dots to show a bond Max 3 of any 4 marks (M2-5) for wrong organic reactant or wrong organic product (if shown) or secondary carbocation Max 2 of any 4 marks in the mechanism for use of bromine Do not penalise the correct use of sticks Page 55 of 92

56 For M5, credit attack on a partially positively charged carbocation structure but penalise M4 M6 is high demand and must refer to product being formed from/via correct class of carbocation M7 is high demand and must be clear answer refers to stability of carbocations (intermediates) not products Candidate that states that products are carbocations would lose M6 and M7 M6,7 allow carbonium ion in place of carbocation; or a description of carbocation in terms of alkyl groups/ number of carbon atoms joined to a positive C When asked to outline a mechanism, candidates are expected to draw a mechanism with curly arrows (specification ). On this occasion only we would allow a detailed description as shown. M2 must describe the movement of a pair of electrons / curly arrow from the C=C towards the H atom of the H-Br molecule M3 must describe the breaking of the H-Br bond with the bonding pair of electrons moving to the Br / curly arrow from H-Br bond to Br M4 is for the structure of the tertiary carbocation (i.e. positive C bonded to one methyl and two ethyl groups) M5 must describe the movement of a pair of electrons from the Br ion to the positive C atom of the carbocation / curly arrow from the lone pair of electrons on the negatively charged bromide ion towards the positively charged C atom (of either a secondary or) of a tertiary carbocation [8] 5 (a) (i) fractional distillation or fractionation (iii) (iv) C 9 H 20 only C H O 2 CO 2 + 2H 2 O C H O 2 C + 2H 2 O (b) (i) C 0 H 22 C 3 H 6 + C 7 H 6 correctly drawn structure of methylpropene (insist on clearly drawn C-C and C=C bonds) Page 56 of 92

57 (c) Any two from o o o chemically similar or chemically the same or react in the same way same functional group same general formula o differ by CH 2 (penalise same molecular formula or same empirical formula) 2 [8] 6 7 B (a) [] (b) (c) Stage : consider the groups joined to right hand carbon of the C=C bond Extended response Maximum of 5 marks for answers which do not show a sustained line of reasoning which is coherent, relevant, substantiated and logically structured. Consider the atomic number of the atoms attached M can be scored in stage or stage 2 C has a higher atomic number than H, so CH 2 OH takes priority Stage 2: consider the groups joined to LH carbon of the C=C bond Both groups contain C atoms, so consider atoms one bond further away C, (H and H) from ethyl group has higher atomic number than H, (H and H) from methyl group, so ethyl takes priority Page 57 of 92

58 Stage 3: conclusion The highest priority groups, ethyl and CH 2 OH are on same side of the C=C bond so the isomer is Z Allow M5 for correct ECF conclusion using either or both wrong priorities deduced in stages and 2 The rest of the IUPAC name is 3-methylpent-2-en--ol (d) Moles of maleic acid = 0.0 / 6.0 = AND mass of organic product expected = ( ) 98.0 = 8.45 g Or moles of organic product formed = 6.53 / 98.0 = % yield = / 8.45 OR = 00 ( ) / ( ) = = 77.3% AND statement that the student was NOT correct [0] 8 (a) (Compounds with the) same molecular formula but different structural / displayed / skeletal formula (b) (basic) elimination Mechanism points: Correct arrow from lone pair on :OH to H on C adjacent to C Br Correct arrow from C H bond to C C Correct arrow from C Br bond to Br Structure of chosen product Page 58 of 92

59 OR [6] 9 (a) Alkenes (b) (c) (d) Correctly drawn molecule of cyclobutane or methyl cyclopropane, need not be displayed formula C 6 H 4 (or correct alkane structure with 6 carbons) Poly(but-2-ene) High pressure Allow hexane or any other correctly named alkane with 6 carbons Allow pressure MPa Mention of catalyst loses the mark Page 59 of 92

60 (e) This question is marked using levels of response. Refer to the Mark Scheme Instructions for Examiners for guidance on how to mark this question. Level 3 All stages are covered and the explanation of each stage is generally correct and virtually complete. Answer communicates the whole process coherently and shows a logical progression from stage and stage 2 (in either order) to stage marks Level 2 All stages are covered but the explanation of each stage may be incomplete or may contain inaccuracies OR two stages are covered and the explanations are generally correct and virtually complete. Answer is mainly coherent and shows progression. Some steps in each stage may be out of order and incomplete. Level Two stages are covered but the explanation of each stage may be incomplete or may contain inaccuracies, OR only one stage is covered but the explanation is generally correct and virtually complete. 3 4 marks Answer includes isolated statements but these are not presented in a logical order or show confused reasoning. 2 marks Level 0 Insufficient correct chemistry to gain a mark. Indicative chemistry content Stage : consider effect of higher temperature on yield (Or vice versa for lower temperature) Le Chatelier s principle predicts that equilibrium shifts to oppose any increase in temperature Exothermic reaction, so equilibrium shifts in endothermic direction / to the left So a Higher T will reduce yield 0 marks Page 60 of 92

61 Stage 2: consider effect of higher temperature on rate (Or vice versa for lower temperature) At higher temperature, more high energy molecules more collisions have E>Ea So rate of reaction increases / time to reach equilibrium decreases Stage 3: conclusion Industrial conditions chosen to achieve (cost-effective) balance of suitable yield at reasonable rate [] 0 (a) 2,2,4-trimethylpentane (b) 5 (c) C 20 H 42 C 8 H 8 + 2C 3 H 6 + 3C 2 H 4 (d) (e) Mainly alkenes formed 4 (monochloro isomers) (f) (g) C 8 H 7 35Cl = = 48.0 and C 8 H 7 37Cl = = 50.0 Both required M r of this C 8 H 7 Cl = 48.8 Page 6 of 92

62 MF = C 8 H 0 Cl 8 (h) = 2.05 : 2.56 : 2.05 Simplest ratio = = :.25 : Whole number ratio ( 4) = 4 : 5 : B C B [2] [] [] [] 4 (a) Saturated single bonds only / no double bonds Hydrocarbon contains carbon and hydrogen (atoms) only (b) C 6 H O 2 6CO + 7H 2 O (c) Allow multiples (On combustion) SO 2 produced Allow equation to produce SO 2. Ignore sulfur oxides. Which causes acid rain If formula shown it must be correct M2 is dependent on M. But if M is sulfur oxides, allow M2. For M2 allow consequence of acid rain or SO 2. Ignore greenhouse effect and toxic (d) (i) C 6 H 34 C 8 H 8 + C 2 H 4 + 2C 3 H 6 Allow multiples Page 62 of 92

63 polypropene / propan(- or 2-)ol / propane(-,2-)diol / isopropanol / propanone / propanal Accept alternative names Ignore plastic and polymer (iii) (e) Allow any unambiguous representation (f) 2,4-dichloro-2,4-dimethylhexane Only but ignore punctuation [0] 5 (a) Crude oil OR petroleum Not petrol. Fractional distillation / fractionation Not distillation alone. (b) C 2 H O 2 2CO + 3H 2 O Allow balanced equations that produce CO 2 in addition to CO. Accept multiples. (c) (i) M Nitrogen and oxygen (from air) react / combine / allow a correct equation If nitrogen from petrol / paraffin / impurities CE = 0 / 2. Page 63 of 92

64 M2 at high temperatures Allow temperatures above 000 C or spark. Not just heat or hot. M2 dependent on M. But allow mark for nitrogen and oxygen together at high temperatures. 2NO + O 2 2NO 2 Allow multiples. (iii) 4NO 2 + 2H 2 O + O 2 4HNO 3 Allow multiples. (d) (i) C n H 2n+2 Allow C x H 2x+2 CnH2n+2 Allow CxH2x+2 C 2 H 26 C 6 H 4 + C 6 H 2 Only. C 3 H 7 Only. (iii) Zeolite / aluminosilicate(s) Ignore aluminium oxide. Larger molecule / longer carbon chain / more electrons / larger surface area More / stronger van der Waals forces between molecules Allow dispersion forces / London forces / temporary induced dipoledipole forces between molecules. If breaking bonds, CE = 0 / 2. (e) 2,2,3,3,4,4-hexamethylhexane Only. Ignore punctuation. Chain Ignore branch(ed). Page 64 of 92

65 Penalise C CH 3 CH 2 (f) Cl 2 Only. Cl Cl Not CL 2 or Cl2 or CL2 or Cl 2 or CL 2. Ignore Chlorine. [6] 6 (a) (i) M (Compounds / molecules with) the same structural formula Penalise M if same structure or different structural / displayed formula. M2 with atoms / bonds / groups arranged differently in space OR atoms / bonds / groups with different spatial arrangements / different orientation Ignore references to same molecular formula or same empirical formula. Mark independently. 2 Credit C H 3 C Credit C 2 H 5 Page 65 of 92

66 (b) M Br 2 OR bromine (water) OR bromine (in CCl 4 / organic solvent) If M, has no reagent or an incorrect reagent, CE=0. Ignore acidified. M2 Isomer : decolourised / goes colourless / loses its colour For M penalise Br (or incorrect formula of other correct reagent), but mark on. M3 Isomer 2: remains orange / red / yellow / brown / the same OR no reaction / no (observable) change OR reference to colour going to the cyclopentane layer For M, it must be a whole reagent and / or correct formula. If oxidation state given in name, it must be correct. If manganate OR manganate(iv) or incorrect formula, penalise M, but mark on. Alternatives : potassium manganate(vii) M KMnO 4 in acid M2 colourless M3 purple M KMnO 4 in alkali / neutral M2 brown solid M3 purple Credit for the use of iodine M iodine (solution / in KI) M2 colourless M3 (brown) to purple (credit no change) Credit for the use of concentrated H 2 SO 4 M concentrated H 2 SO 4 M2 brown M3 no change / colourless Ignore goes clear. Ignore nothing (happens). Ignore no observation. No credit for combustion observations. (c) (i) (Both infrared spectra show an absorption in range) 620 to 680 (cm ) Ignore reference to other ranges (eg for C H or C C). 3 The fingerprint (region) / below 500 cm will be different or its fingerprinting will be different OR different absorptions / peaks are seen (in the region) below 500 cm (or a specified region within the fingerprint range) Allow the words dip OR spike OR low transmittance as alternatives for absorption. QoL Page 66 of 92

67 (d) All bonds must be drawn. Ignore bond angles. (e) (i) M Electrophilic addition M both words needed. Penalise one mark from their total if half-headed arrows are used. M2 must show an arrow from the double bond towards the H atom of the H Br molecule M2 Ignore partial negative charge on the double bond. M3 must show the breaking of the H Br bond M3 Penalise incorrect partial charges on H Br bond and penalise formal charges. M4 is for the structure of the tertiary carbocation Penalise M4 if there is a bond drawn to the positive charge. Penalise once only in any part of the mechanism for a line and two dots to show a bond. M5 must show an arrow from the lone pair of electrons on the negatively charged bromide ion towards the positively charged carbon atom of either a secondary or a tertiary carbocation For M5, credit attack on a partially positively charged carbocation structure but penalise M4. Max 3 of any 4 marks in the mechanism for wrong organic reactant or wrong organic product (if shown) or secondary carbocation. Max 2 of any 4 marks in the mechanism for use of bromine. Do not penalise the correct use of 'sticks. NB The arrows here are double-headed 5 Page 67 of 92

68 M Reaction goes via intermediate carbocations / carbonium ions M is a lower demand mark for knowledge that carbocations are involved. M2 (scores both marks and depends on M) Tertiary carbocation / carbonium ion is more stable (than the secondary carbocation / carbonium ion) OR Secondary carbocation / carbonium ion is less stable (than the tertiary carbocation / carbonium ion) M2 is of higher demand and requires the idea that the secondary carbocation is less stable or the tertiary carbocation is more stable. Reference to incorrect chemistry is penalised. A carbocation may be defined in terms of alkyl groups / number of carbon atoms, rather than formally stated. 2 Page 68 of 92

69 (f) M Elimination M credit base elimination but no other qualifying prefix. Penalise one mark from their total if half-headed arrows are used. M2 must show an arrow from the lone pair on oxygen of a negatively charged hydroxide ion to a correct H atom Penalise M2 if covalent KOH M3 must show an arrow from a correct C H bond adjacent to the C Br bond to a correct C C bond. Only award if an arrow is shown attacking the H atom of a correct adjacent C H bond (in M2) M4 is independent provided it is from their original molecule BUT penalise M2, M3 and M4 if nucleophilic substitution shown Award full marks for an E mechanism in which M2 is on the correct carbocation NB The arrows here are double-headed Penalise M4 for formal charge on C or Br of the C Br bond or incorrect partial charges on C Br. Penalise M4 if an additional arrow is drawn from the Br of the C Br bond to, for example, K +. Ignore other partial charges. Penalise once only in any part of the mechanism for a line and two dots to show a bond. Max 2 of any 3 marks in the mechanism for wrong reactant or wrong organic product (if shown) or a correct mechanism that leads to the alkene 2-methylbut-2-ene. Credit the correct use of sticks for the molecule except for the C H being attacked. M5 hydroxide ion behaves as a base / proton acceptor / electron pair donor / lone pair donor Penalise M5 if nucleophile. 5 [2] 7 (a) (i) (nucleophilic) addition-elimination Not electrophilic addition-elimination Ignore esterification Page 69 of 92

70 M3 for structure If wrong nucleophile used or O H broken in first step, can only score M2. M2 not allowed independent of M, but allow M for correct attack on C+ + rather than δ+ on C=O loses M2. If Cl lost with C=O breaking lose M2. M3 for correct structure with charges but lone pair on O is part of M4. Only allow M4 after correct / very close M3. Ignore HCl shown as a product. a (ppm) or single value or range entirely within this range If values not specified as a or b then assume first is a. b (ppm) or single value or range entirely within this range 4 Must have trailing bonds, but ignore n. OR OCH 2 CH 2 CH 2 CH 2 CO OR CH 2 CH 2 CH 2 CH 2 COO Allow but not - C 4 H 8 one unit only Condensation Page 70 of 92

71 (b) Tollens Fehling s / Benedicts Acidified potassium dichromate Penalise wrong formula for Tollens or missing acid with potassium dichromate but mark on. J No reaction / no (visible) change / no silver mirror No reaction / no (visible) change / stays blue / no red ppt No reaction / no (visible) change / stays orange / does not turn green Ignore clear, nothing. Penalise wrong starting colour for dichromate. K Silver mirror / grey ppt Red ppt (allow brick red or red-orange) (orange) turns green J K Two (peaks) Allow trough, peak, spike. Four (peaks) Ignore details of splitting. If values not specified as J or K then assume first is J. (c) If all the structures are unlabelled, assume that the first drawn ester is L, the second ester is M; the first drawn acid is N, the second P. The cyclic compound should be obvious. L ester OR H 2 C=C(CH 3 )COOCH 3 All C 5 H 8 O 2 L to P must have C=C. Allow CH 3. Allow -CO 2 CH 3 etc. Allow CH 2 C(CH 3 )COOCH 3. Page 7 of 92

72 M ester CH 3 CH=CHCOOCH 3 CH 3 CH=CHOOCCH 3 CH 3 CH=C(CH 3 )OOCH CH 3 CH=CHCH 2 OOCH CH 3 CH 2 CH=CHOOCH Allow either E Z isomer. Allow CH 3 or C 2 H 5 but not CH 2 CH 3. Allow CH 3 CHCHCOOCH 3 etc. N acid (CH 3 ) 2 C=CHCOOH H 2 C=C(CH 3 )CH 2 COOH H 2 C=C(COOH)CH 2 CH 3 Allow CH 3 or C 2 H 5 but not CH 2 CH 3. Allow CO 2 H. Not cyclic isomers. Not the optically active isomer. Allow (CH 3 ) 2 CCHCOOH etc. P acid Allow CO 2 H. CH 3 CH(COOH)CH=CH 2 Allow CH 3 CH(CO 2 H)CHCH 2 or CH 3 CH(CO 2 H)C 2 H 3. Page 72 of 92

73 Q Not cyclic esters. [9] 8 (a) (i) (Compounds with the) same molecular formula Allow same number and type of atom for M Ignore same general formula. But different structural formula / different displayed formula / different structures / different skeletal formula M2 dependent on M Not different positions of atoms / bonds in space. (iii) (iv) But-2-ene Allow but-2-ene. Allow but 2 ene. Ignore punctuation. (2)-methylprop-()-ene Do not allow 2-methyleprop--ene. Do not allow skeletal formulae. Penalise missing H and missing C Page 73 of 92

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