ORGANIC CHEMISTRY

1.(a) Methane is the first member of of the homologous series of alkanes .

(i) Write the general formula for an alkane. (1)
(ii) State how the chemical properties and a named physical property of members of a homologous series change, if at all, as the
molecular mass increases. (2)
(b) The formula C2H4Cl2 can represent two isomers
(i) Explain what is meant by isomers ? (1)
(ii) Draw the displayed formula for the two isomers of C 2H4Cl2 (2)
(iii) Write the empirical formula for C2H4Cl2

2.(i) Draw a displayed formula for C4H10 and C4H8. Use the formulae to explain the difference between saturated and unsaturated
hydrocarbons in terms of the bonds present in the molecules. (4)
(ii) Give a test, and the observation, that would distinguish between C4H10 and C4H8 (2)
(iii) Write an equation for a reaction that occurs when the test is performed. (1)

3. (a) Describe how ethanol is obtained from ethene with equation. (4)
(b) write the name and formula of the organic compound formed when ethanol reacts with each of the following.
(i) Sodium metal (1)
(ii) Acidified potassium dichromate (VI) (1)
(iii) Phosphorous pentachloride (1)

4.(a) Nylon is polyamide that can be made from the monomers below.

HOOC(CH2)4COOH H2N(CH2)6NH2
(i) Complete the central section to show the arrangement of all the bonds in the missing part of the polymer chain of nylon.
─C─(CH2)4─……………………………………… ─(CH2)6─N─
║ │
O H
(1)
(ii) What is name given to this type of polymerization ? (1)

(b) Chloroethane, CH2=CHCl, can be polymerized to form poly(chloroethene).

(i). Draw the displayed formula of chloroethene) (1)
(ii) Draw the displayed formula of the repeating unit in poy(chloroethene) (1)
(iii) What is the name given of this type of polymerization? (1)
(iv) Use chloroethene and poly(chloroethene) to explain the difference between the terms saturated and unsaturated.
(2)
(v) Draw the displayed formula for the product of the reaction between chloroethene and chlorine. (1)
(c) But-1-ene can undergo polymerization
(i) Name the type of polymerization. (1)
(ii) Draw the repeating unit of this polymer. (1)
(d) Suggest why alkenes burn with a sootier flame than alkanes. (1)
(e) The following diagram represents a part of a terylene chain.
̶ O ̶ (CH2)2 ̶ OC ̶ (CH2)4 ̶ OC ̶ (CH2)2 ̶ OC ─ (CH2)4 ─ OC ─
║ ║ ║ ║
O O O O
Draw diagram of the two monomer molecules that could be used to form this terylene. (2)

5.Name the reagent , conditions and show the equations of reaction to produce chloroethane from ethane, ethene and ethanol.
(6)

6. Here are some statements about the compound ethene.

1
● ethene has the displayed formula
● ethene is a gas at room temperature
● ethene burns with a smoky flame
● ethene is unsaturated
● ethene is insoluble in water
● ethene can be prepared from ethanol
● ethene is used to make the polymer poly(ethene)
(a) (i) State why ethene is described as unsaturated. (1)
(ii) Describe a chemical test to show that ethene is an alkene.
(2)
(b) (i) Complete the following equation that represents the preparation of ethene from ethanol. (1)
C2H5OH → C2H4 + .................
(ii) What is the name given to this type of reaction? (1)
(c) Complete the equation to show the formation of poly(ethene) from ethene.

(2)
7. These are the displayed formulae of six organic compounds.

(a) Use the letters above to select

(i) the compound that is not a hydrocarbon.
(1)
(ii) one compound with the empirical formula CH2
(1)
(iii) one compound that can form a polymer.
(1)
(b) Describe a test that will distinguish between compounds Q and T, and state the observation made with compound T.
(2)

(c) Draw the displayed formula of an alkene containing four carbon atoms. (1)
(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? (1)
(ii) State two other features of a homologous series. (2)

(e) The displayed formulae below represent isomers.

2
Explain what isomers are. (2)
8. 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.
(1)
(b) Decane and ethene, C2H4, are produced during the cracking of eicosane, C20H42 Ethene is used to make poly(ethene).

(i) What is the name given to this type of polymerisation? (1)

(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)
9. There are two important ways to manufacture ethanol.
Reaction 1 C2H4 + H2O → C2H5OH
Reaction 2 C6H12O6 → 2C2H5OH + 2CO2
(a) (i) Identify one raw material that could be used as the source of C6H12O6
(1)
(ii) Reaction 2 uses a catalyst called zymase, which is present in yeast. Identify the catalyst used in reaction 1.
(1)
(iii) In both reactions it is important to control the temperature. State why the temperature in reaction 2 is kept below 40 °C.
(1)
(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)

10. Ethanol can be made both by fermentation and by the addition of steam to ethene.
(a) (i) Name the organic compound required for fermentation. (1)
(ii) State the conditions under which fermentation most readily takes place. (2)

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(b) Write an equation for the reaction between steam and ethene.
(1)
(c) (i) Name the third member of the alcohol homologous series.
(1)
(ii) Draw the displayed formula of this compound, showing all atoms and bonds.
(1)

11. The structural formulae of some compounds containing the element carbon are shown.

A B C D
Choose from the compounds A, B, C, and D to answer the questions below. Each compound can be used once, more than once or
not at all. Which one of these compounds is
(i) a poisonous gas produced by the incomplete combustion of hydrocarbons,
(1)
(ii) an unsaturated hydrocarbon. (1)
(iii) formed when propene reacts with steam. (1)
(iv) an isomer of butane? (1)
(v) Name compound B (1)
(b) The structures of three organic molecules are shown below.

(i) Describe an industrial process to make ethanol from ethene. (3)

(ii) Name a reagent that can be used to convert ethanol into ethanoic acid. (1)
(c) Ethanoic acid is a weak acid. It reacts with magnesium giving a gas and a magnesium salt.
(i) What is meant by the term weak acid? (1)
(ii) Name the gas formed. (1)
(iii) What is the formula of the magnesium salt formed? (1)

12. Plastics are made of macromolecules called polymers. In the middle of the Pacific Ocean there is a huge area of water that is
contaminated with small bits of plastics. The waste plastics have been washed away from coastlines.
(a) Part of the structure of one of the polymers found in the ocean is shown below.

(i) Name this type of polymer. (1)

(ii) Draw the structure of the monomer used in the manufacture of this polymer. (1)
(iii) Explain why this polymer is described as a saturated hydrocarbon. (1)
(b) Suggest why this polymer is not destroyed in water. (1)

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13.(a) Ethanol is made from a sugar solution by fermentation.
(i) Name a catalyst for the reaction. (1)
(ii) Give a temperature at which the reaction is usually carried out. (1)
(iii) State how solid impurities are removed. (1)
(iv) State how the oxidation of ethanol is removed. (1)
(v) Name the method used to obtain pure ethanol from the aqueous mixture. (1)
(vi) Write the equatin for the formation of ethanol from glucose. (1)
(b). Give two advantages and two disadvantages of this method to manufacture of ethanol compare with using ethene as a starting
material. (4)

14.(a). (i) Give the empirical formula of butene. (1)

(ii). Write the molecular formula of butene. (1)
(iii) Draw the structural formula of but-2-ene. (1)
(iv) Draw the displayed formula but-1-ene. (1)
(v) Draw the maximum possible isomer of butene with name. (1)
(vi) Mention the state of butene at room temperature. (1)
(vii) Write a chemical equation for the complete combustion of butene. (1)
(viii) Draw the polymer unit of butene with three repeating unit. (1)

15. Insert the missing words into the following account of a method that can be used to prepare aqueous ethanol in the laboratory
by fermentation.

An aqueous solution of ............................................................. was placed in a flask and .............................................................

............................................................. was added. An air-lock was fitted to maintain ............................................................. condition and the

apparatus was left at a temperature of about ............................................................. for a few days. The mixture was then

............................................................. to remove solid impurities and the solution was concentrated by.............................................................

.............................................................. .
(Total 6 marks)
16.(a).Name two fractions obtained from fractional distillation of crude oil. Give ONE use for each of them.

Fraction-1 ......................................................................................................................................Use...................................................................................................................................
Fraction-2.................................................................................................................................Use..........................................................................................................................................
(4)
(b). (i) Name the process used to to break down long chain hydrocarbon into shorter chain molecules.
(ii). Complete the following equation to show the breakdown into propene and the other hydrocarbon.

C6H4 → .................................................................... + ........................................................................................

(1)
(c) Draw the structure of poly(propene) (1)
(d) Some organic compounds can be made into polymers. Use word from the box to complete the sentence. Each word may be used
once , more than once or not at all.
Giant , Monomers, Plastic, Small.

Polymers are ........................................... molecules formed when molecules called................................................. join together.
(2)
17.(a) Us e following compounds to answer the question below.

Ethene, Ethane, Ethanol, Ethanoic acid

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Which of these componds:
(i) Is saturated hydrocarbon..............................................................................................................................................................................
(ii) Has a relative molecular mass of 60.................................................................................................................................................
(iii) Is the least reactive with most reagents...................................................................................................................................
(iv) Are soluble in water...........................................................................................................................................................................................
(v) React with PCl5 to give a colourless gas which forms a white smoke in the presence of ammonia gas.
................................................................................................................................ ............................................................................

(vi) Decolourise bromine water.....................................................................................................................................................................

(vii) React with sodium to give a flammable colourless gas..........................................................................................
(viii) Two compounds form with each other.....................................................................................................................................
(ix) React with CaCO3 to produce CO2 gas. ......................................................................................................................................
(9)

(b) The following molecules can react together to form polymer.

HOOC (CH2)4COOH , HO(CH2)2OH
(i)Name the type of polymerisation....................................................................................................................................
(ii)What substance is lost? ..............................................................................................................................................................
(iii)Name the polymer formed..................................................................................................................................................
(iv)Draw digram of polymer unit

(4)
(c) The following diagram represents part of nylon chain.
̶ NH ̶ (CH2)6 ̶ NHCO ̶ (CH2)4 ̶ CONH ̶ (CH2)6 ̶ NHCO ̶ (CH2)4 ̶ CO ̶
(i) Draw the TWO monomers
Monomer-1
Monomer-2
(2)
(ii) Draw the repeating unit
(1)
(d) Show equation of reactions to produce chloroethane from
(i) C2H6...............................................................................................................................................................................................................................................................................................

(ii) C2H4.............................................................................................................................................................................................................................................................................................

(iii)C2H5OH..................................................................................................................................................................................................................................................................................
(3)
18. Crude oil is a mixture of many different compounds. During industrial refining, crude oil is first separated into fractions.
(i) What is the name of the process used to obtain fractions from crude oil? (1)
Four of the fractions obtained from crude oil are:
bitumen
diesel
gasoline
kerosene
(i) Which of these four fractions is the most viscous? (1)
(ii) Which of these four fractions is the most volatile? (1)
(iii) Which of these four fractions is used in making roads? (1)
(iv) Name two other fractions obtained from crude oil. (2)

19.This question is about the synthetic polymer nylon.

(a) Poly(ethene) is an addition polymer. What type of polymer is nylon? (1)
(b) Nylon can be made using the monomers A and B represented in the diagrams.

H2N H2N HOOC COOH

A B

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(i) What type of compound is monomer A? (1)
(ii) What type of compound is monomer B?
(1)
(iii) Draw a diagram to show the structure of the polymer formed from A and B. You must draw enough of the structure to make the
repeat unit clear.
(3)
(c) Nylon has a simple molecular structure. Use words from the box to complete the sentences.
Each word may be used once, more than once or not at all.

Ions , High, Low, Molecules, Strong , weak

Nylon has a ......................................... melting point. This is because there are ......................................... forces between the

........................................ that make up the structure.

(3)
20. Crude oil is a mixture of hydrocarbons. The diagram shows how the hydrocarbons in crude oil can be separated by Fractional
Distillation

(a) Use the information in the diagram to help you answer these questions.
(i) Name the fraction that does not evaporate during fractional distillation. (1)
(ii) Name the fraction that does not condense as it rises up the fractionating column. (1)
(iii) Name the liquid fraction that leaves the column at the lowest temperature. (1)
(b) The table shows uses of some fractions obtained from crude oil. Complete the table by selecting fractions from the diagram.
Use of fraction Name of fraction
Aviation fuel
Car fuel
Road surface
(3)
(c) Kerosene contains hydrocarbons.
(i) Complete the word equation for the complete combustion of kerosene.

kerosene + .............................................................. → ..................................................................... + .......................................................................

(3)
(ii) Name the poisonous gas that may form during the incomplete combustion of kerosene. (1)
(iii) Incomplete combustion may form a black solid called soot. Name the element present in soot. (1)
(d) Some organic compounds can be made into polymers.
(i) Use words from the box to complete the sentence. Each word may be used once, more than once or not at all.
giant monomer plastic small

Polymers are .......................................... molecules formed when molecules called .......................................................... join together.
(2)
(ii) Place a cross ( ) in the box next to the repeat unit of poly(ethene).

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 (1)
21. Crude oil is a complex mixture of hydrocarbons. The diagram shows how the hydrocarbons in crude oil can be separated into
fractions by fractional distillation.

(a) Use words to complete the description of fractional distillation. Each word may be used once, more than once, or not at all.
Burns, condenses, decomposes, evaporates, higher, lower
When the crude oil is heated, most of it ........................................................................... Each fraction ......................................................................... at a

different level. The temperature changes from the top to the bottom of the column. The temperature

is...........................................................................at the top of the column. The kerosene fraction collects at a higher level than the fuel

oil fraction because kerosene has a...........................................................................boiling point range.

(4)
(b) Fractions A and B are both used in fuels for road vehicles. State the name of

fraction A .....................................................................................................................................................................................................................................................................................

fraction B .....................................................................................................................................................................................................................................................................................
(2)
(c) One compound present in fraction A is octane. Write a word equation for the complete combustion of octane.
(2)
(d) The incomplete combustion of octane produces a poisonous gas. Identify the gas and explain why it is poisonous.
(2)
22.(a) Describe how ethane is produced during refining of crude petroleum. (3)
(b) When ethane is shaken with bromine water, compound A is formed. Draw the structural formula of compound A.
(1)
(c) Ethene can be oxidized to form compound B . This compound has following composition by mass
Carbon 38.7% hydrogen 9.7% oxygen 51.6%
(i) Calculate the empirical formula of compound B. (1)
(ii) The relative molecular mass of compound B is 62. What is the molecular formula of compound B (2)
(iii) Suggest a structural formula for compound . (1)
(d) Ethene can be converted to ethanoic acid as follows :
Ethane → compound C → ethanoic acid
(i) Identify compound C. (1)
(ii) What type of reaction is taking place when compound C is made into ethanoic acid. (1)

(iii) Write the equation of complete combustion of ethane. (1)

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23. The structures of some organic compounds are shown below.

(a) Name compound A. (1)

(b) Which two of the compounds A to E belong to the same homologous series? (1)
(c) (i) Which one of the compounds A to E has the same functional group as ethanol? (1)
(ii) Draw the structure of ethanol, showing all atoms and bonds. (2)
(iii) Describe how ethanol is made in industry from ethene.
(2)
(d) (i) Which one of the compounds A to E is an unsaturated hydrocarbon? (1)
(ii) Describe a chemical test for an unsaturated hydrocarbon. (2)
(e) Compound E is acidic.
(i) State the name of compound E. (1)
(ii) Describe a test to show that compound E is acidic. (2)

24. (a) Sugar contains sucrose, C12H22O11 When yeast is added, water reacts with sucrose to form glucose, C 6H12O6 Write a chemical
equation for this reaction. (1)
(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? (1)

(ii) How could the solid yeast be removed from the mixture? (1)
(c) Ethanol can be converted into chloroethene, CH2 CHCl, in three stages.
Stage 1 Ethanol is dehydrated to form ethene, CH 2 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? (1)

(ii) Identify the catalyst used in the reaction in Stage 1. (1)

iii) Suggest the name or formula of the substance used to react with ethene in Stage 2. (1)
(iv) Write a chemical equation for the reaction in Stage 3. (1)
(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.

(1)
(ii) Describe, in terms of structure and bonding, what happens when chloroethene molecules are converted into poly(chloroethene).
(3)

25.The table shows the structures of six organic compounds, A to F.

9
(a) The letter of the compound in the table that is not shown as a displayed formula is (1)

(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)

(ii) State what is meant by the term unsaturated, and give the letter of one compound in the table that is unsaturated.
(2)

(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.

Letters ....................................................................................................................................................... and ...........................................................................................................................

(3)

(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)

(ii) Give the letters of two adjacent members of the same homologous series shown in the table.

Letters ................................................................................................................................ and ...................................................................................................................................................

(1)
(d) (i) Compound G has the molecular formula C2H4Br2 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. (1)
(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. (1)

26. (a) Explain what is meant by the term isomerism. (2)

(b) The displayed formula of heptane (C7H16) is

10
Which one of the displayed formulae below does not represent an isomer of heptane?Place a cross (×) in the box to indicate your
answer.

(1)
(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.

(1)

(ii) Complete the following diagram to show the structural formula of heptene (C 7H14) by inserting lines to represent the covalent
bonds between the carbon atoms.

(2)
(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)

(e) Explain, in terms of the bonds present, why heptane is described as saturated and heptene as unsaturated.
(2)
27. (a) Plastic bags used to store food are made from a polymer. Ethene is the monomer used to make the polymer for some plastic
bags.

11
(i) Name the polymer that is made from ethene. (1)
(ii) Use a word from the box to complete the sentence about ethene.

Chromatography condensing cracking crystallising

Ethene is made by breaking down large hydrocarbon molecules into smaller hydrocarbon molecules, using a process called
(1)
(b) The hydrocarbons used to make ethene are called alkanes. They are obtained from crude oil. The boiling point of an alkane is
related to the number of carbon atoms in the molecule.
Number of carbon atoms in molecule 5 6 7 8 9
Boiling point in °C 36 69 99 125 151

(i) Use the data in the table to complete the bar chart.

(2)

(ii) What is the relationship between the boiling point of an alkane and the number of carbon atoms in its molecule?
(1)
(c) Many plastic bags are not biodegradable. Used plastic bags can be
A buried underground, which is called landfill
or
B burned to release energy, which also produces large amounts of gases.
Suggest which of these methods of disposal is better for the environment, giving two reasons for your choice.
Choice ................................................................................................................................................................................................................................................................................................

Reason 1 ...........................................................................................................................................................................................................................................................................................

Reason 2 ..........................................................................................................................................................................................................................................................................................
(2)
28. 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.
Statement Fractional distillation Cracking
Crude oil is heated √
A catalyst may be used
Alkenes are formed
Decomposition reactions occur
Fuels are obtained
Separation is the main purpose
(5)
(b) The formula CH3CH2CH2CH2CH3 represents one of the compounds in crude oil.
(i) Give the molecular formula of this compound. (1)

12
(ii) Give the displayed formula of this compound. (1)
(iii) Give the empirical formula of this compound. (1)
(iv) Give the name of this compound. (1)
(v) Give the general formula of the homologous series that contains this compound. (1)
(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).
C2H4 + ...................O2 → ...................CO2 + ...................H2O
(2)
(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)
(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. Assume that all of the ethene is converted into
ethanol and that the molar volume of ethene is 24 dm3 at rtp. (3)

29. The diagram shows some important conversion processes used in the oil industry.

(a) Process 1 is called

A catalytic cracking
B condensation polymerisation
C fractional distillation
D thermal decomposition
(1)
(b) Describe the differences between crude oil and kerosene. In your answer you should refer to
• the average size of the molecules in the two liquids
• the covalent bonding in the molecules
• the viscosities of the two liquids
(3)
(c) The equation for one reaction that could occur in process 2 is
CxHy → C5H12 + 2C2H4
(i) Deduce the formula of CxHy (1)
(ii) Give the name of the compound C5H12 (1)
(iii) Draw the displayed formula of C2H4 (1)
(d) The structural formula of chloroethene formed in process 3 is CH2CHCl The polymer formed in process 4 is poly(chloroethene).
Draw the displayed formula for the repeat unit of poly(chloroethene). (2)
(e) Poly(chloroethene) is formed by addition polymerisation. Nylon is formed by condensation polymerisation.
(i) How does condensation polymerisation differ from addition polymerisation? (1)
(ii) Poly(chloroethene) and nylon do not biodegrade easily. What is meant by the term biodegrade? (2)
(iii) What feature of addition polymers makes it difficult for them to biodegrade? (1)

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30. The table gives some data about the first six members of a homologous series of compounds called the alkanes.
Alkane Molecular formula Relative formula mass Boiling point in oC
methane CH4 16 –164
ethane C2H6 30 –87
propane C3H8 44 –42
butane C4H10 0
pentane C5H12 72
hexane 86 69

(a) Complete the table by

• giving the molecular formula of hexane
• giving the relative formula mass of butane
• suggesting the boiling point of pentane
(3)
(b) What does the data show about the relationship between boiling point and relative formula mass? (1)
(c) The molecular formula of ethene is C2H4. Ethene and ethane are in different homologous series. Explain how the formulae of
these compounds show that they are in different series. (1)
(d) (i) In the table, draw displayed formulae for the two alkanes with the molecular formula C4H10 (2)
(ii) What is the name given to compounds that have the same molecular formula but different displayed formulae?
(1)
(e) The reaction between ethane and bromine (Br2) is similar to the reaction between methane and bromine.
(i) Write a chemical equation for the reaction between ethane and bromine. (2)
(ii) What is the name given to the type of reaction that occurs when ethane reacts with bromine? (1)
(iii) Suggest the condition necessary for this reaction to occur. (1)

31. The diagram shows the displayed formulae of five hydrocarbons A, B, C, D and E.

(a) Give the letter of a hydrocarbon to answer these questions. You may use each letter once, more than once or not at all.
(i) Which hydrocarbon is the main component of natural gas? (1)
(ii) Which other hydrocarbon is produced, together with D, when pentane (C 5H12) is cracked? (1)
(iii) Which hydrocarbon can undergo an addition reaction with hydrogen to form B? (1)
(b) Give the molecular formula and the empirical formula of E. (2)
(c) Hydrocarbons A, B, D and E all belong to the same homologous series.
(i) Give the name and the general formula of this homologous series. (2)
(ii) Draw the displayed formula of an isomer of E. (1)
(d) Two reactions that can occur when hydrocarbon A is burned in air are represented by these equations.
Equation for reaction 1 CH4 + 2O2 →CO2 + 2H2O
Equation for reaction 2 CH4 + 1½O2 → CO + 2H2O
Explain why a different product is formed in reaction 2 and why this product is dangerous. (3)

32. Crude oil is an important source of organic compounds.

(a) The diagram shows how crude oil is separated into fractions in the oil industry.

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(i) What happens to the crude oil in A? (1)
(ii) Most of the compounds in crude oil are hydrocarbons. What is meant by the term hydrocarbons? (2)
(iii) Compare the hydrocarbons in fractions D and F in terms of
• boiling point
• size of molecules
• Viscosity
(3)
(b) Some of the fractions are catalytically cracked. The general equation for some reactions in this process is
alkane → alkane + alkene
(i) State two conditions used in catalytic cracking. (2)
(ii) How does the bonding in an alkene molecule differ from the bonding in an alkane molecule? (1)
(iii) The chemical equation for one cracking reaction is
C16H34 → C8H18 + 2C3H6 + compound Q
Deduce the molecular formula of Q. (1)
(c) The compound with molecular formula C3H6 can be used to make a polymer.
(i) Give the name of the compound C3H6 (1)
(ii) Complete the table of information about this compound.

Type of formula Formula

molecular C3H6
CnH2n
CH2
displayed
(3)
(iii) Complete this structure to show the part of the polymer formed from two molecules of C3H6
––C––C––C––C–– (2)
33. (a) The first two members of the homologous series of alcohols are methanol and ethanol.
(i) Give two characteristics of the compounds in a homologous series. (2)
(ii) The displayed formula for methanol is

Suggest a displayed formula for ethanol, CH3CH2OH (1)

Process Explanation
batch process the fermentation of sugars with yeast
continuous process the hydration of ethene (produced from crude oil) with steam
Compare the two processes in terms of
• the rate at which the ethanol can be produced
• the purity of the product
• the use of finite resources

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 (3)

(c) The equation for the fermentation of glucose is

C6H12O6 → 2CH3CH2OH + 2CO2
A mass of 3600 kg of glucose was completely fermented.
(i) Calculate the amount, in moles, of glucose that was fermented. (Mr of glucose = 180) (2)
(ii) Deduce the amount, in moles, of ethanol produced in this reaction. (1)
(iii) Calculate the volume, in dm3 at rtp, of carbon dioxide produced in this reaction. (1 mol of carbon dioxide occupies 24 dm3 at rtp)
(2)
34. The table shows the displayed formulae of six organic compounds, P, Q, R, S, T and U.

(a) (i) What is the molecular formula of compound S?

(1)
(ii) What is the empirical formula of compound T?
(1)
(b) (i) Give the letters of two compounds that belong to the homologous series of alkenes.
............................................................................................................................................................... and ....................................................................................................................................... .

(1)
(ii) The general formula of this homologous series is

(1)
(c) Which of these conversions is an example of an addition reaction?
A compound P → compound Q B compound Q → compound T
C compound R → compound Q D compound R → compound U
(1)
(d) Complete the table to show the displayed formula and name of the isomer of compound T.
Displayed formula

Name
(2)
(e) The equation represents a reaction between compound P and bromine.

(i) Complete the equation to show the displayed formula of the organic product.

16
 (1)
(ii) State the name of this organic product.
(1)
(iii) State the condition used in this reaction.
(1)
(iv) What term is used for this type of reaction?
A addition B hydration
C neutralization D substitution
(1)
(f ) Old refrigerators may contain substances that harm the ozone layer in the atmosphere. Many new refrigerators use 152a, an
organic compound that does not harm the ozone layer. 152a has the composition by mass C = 36.4%, H = 6.0% and F = 57.6%.
(i) Calculate the empirical formula of 152a.
(3)
(ii) The relative formula mass of 152a is 66 .What is its molecular formula?

molecular formula..............................................................
(1)
35. The diagram shows the separation of crude oil into fractions.

(a) What is the name of this method of separation? (1)

(b) Complete the table by giving the correct fraction, A, B, C, D, E or F, for each description. You may use each letter once, more than
once or not at all.
Fraction Description
contains only gases
is the most viscous
contains bitumen
(c) State the relationship between the number of carbon atoms per molecule and the boiling point of the fraction. (1)

36. Ethene is an unsaturated hydrocarbon.

(a) (i) The molecular formula of ethene is

A CH4 B C2H6
C C2H4 D C3H6
(1)
(ii) Ethene is bubbled into bromine water until there is no further change. What is the appearance of the solution formed?
A brown B colourless

17
 C purple D red
(1)
(iii) Ethene can be formed from ethanol. This type of reaction is called
A dehydration B oxidation
C reduction D substitution
(1)
(b) This apparatus can be used to decompose decane (C 10H22).

(i) What name is given to this type of thermal decomposition?

(1)
(ii) Porous pot contains oxides such as silica and alumina. What is the purpose of the porous pot in this experiment? (1)
(iii) Suggest why the gas collected is a mixture and not pure ethene. (1)
(c) Some reactions of organic compounds are shown below.

(i) Which one of the reactions, A, B, C or D, shows fermentation?............................................................................................................

(ii) Which one of the reactions, A, B, C or D, shows polymerization? .....................................................................................................

(iii) Which one of the reactions, A, B, C or D, shows combustion? ...........................................................................................................

(iv) Which one of the reactions, A, B, C or D, shows cracking? ........................................................................................................................

(4)

37.Ethene is an unsaturated hydrocarbon.

(a) What is the meaning of each of these terms?

unsaturated _______________________________________________________________________________________________
hydrocarbon_______________________________________________________________________________________________
(2)

(b) Ethene can be manufactured by cracking.

(i) State the conditions used for cracking. (2)

(ii) Construct an equation for the cracking of tetradecane, C 14H30, to form ethene and one other hydrocarbon. (1)

(c) Alkenes such as ethene can undergo addition polymerisation.

18
(i) State one use of poly(ethene). (1)

(ii) The diagram below shows a section of a polymer chain.

Deduce the structure of the monomer which is used to make this polymer. (1)

(d) Ethanol can be manufactured by the catalytic addition of steam to ethene.

C2H4 + H2O → C2H5OH

If the reactants are not recycled, only 5% of the ethene is converted to ethanol. Calculate the mass of ethanol formed from 0.4
tonnes of ethene when only 5% of the ethene is converted to ethanol. [1 tonne is 1 000 000 grams] (3)

38. Propane and propene are organic compounds.

(a) State one similarity and one difference between the structures of propane and propene.

similarity _________________________________________________________________________________________________
difference ________________________________________________________________________________________________
(2)

(b) Name a substance that can be used to distinguish between propane and propene. In each case, describe what you would see.

substance ________________________________________________________________________________________________
observation with propane ___________________________________________________________________________________
observation with propene ___________________________________________________________________________________
(2)

(c) Another compound, Z, can be polymerised to form polystyrene. Part of the structure of polystyrene is shown below.

(i) Draw the structure of compound Z.

(ii) Name the two products which are formed by complete combustion of polystyrene.

(iii) Give one advantage of disposing of waste polystyrene by burning. (4)

39.Styrene-butadiene rubber is a synthetic rubber. It is made by polymerising a mixture of the monomers butadiene and styrene.

(a) What type of polymerisation will take place when the monomers polymerise? Explain your reasoning. (2)

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One possible structure for the polymer is shown below.

(b) Give the full structural formula for the repeating unit in this polymer structure.

(2)

40. This is the structure of an ester made in a reversible reaction between a carboxylic acid and an alcohol.

(a) (i) State the conditions for this reaction. (2)

(ii) Draw the structure of the carboxylic acid used in the reaction. (1)

(iii) Write an equation for this reaction. (2)

(b) A student carried out some experiments to compare the relative strengths of dilute ethanoic acid with dilute hydrochloric acid.

(i) Describe a test that can be used to distinguish between dilute ethanoic acid and dilute hydrochloric acid. (2)

(ii) Name a solid substance that will react with both acids. Describe what you will see during the reaction.

substance ________________________________________________________________________________________________
observations_______________________________________________________________________________________________
(2)

41. These diagrams show sections of the polymer chain of two condensation polymers.

(a) (i) Draw a circle around an amide linkage in the diagram. Label this amide.

(ii) Draw a circle around an ester linkage in the diagram. Label this ester. (2)

(b) The formulae of the two monomers used to make nylon are shown below.

Nylon monomers HOOC(CH2)4COOH H2N(CH2)6NH2

Deduce the formulae of the two monomers that are used to make Terylene.

Terylene monomers (2)

(d) Sea fishing nets used to be made from natural fibres. Many nets are now made from nylon. Suggest one advantage, other than
strength, and one disadvantage of using nylon rather than natural fibres to make sea fishing nets.

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advantage_________________________________________________________________________________________________
disadvantage ______________________________________________________________________________________________
(2)

(b) Tartaric acid can also be extracted from grape juice. The structure of tartaric acid is shown below.

(i) Deduce the empirical formula of tartaric acid. (1)

(ii) A solution of tartaric acid was titrated with 0.100 mol/ dm3 potassium hydroxide.

C2H2(OH)2(CO2H)2 + 2KOH → C2H2(OH)2(CO2K)2 + 2H2O

tartaric acid

It required 6.00 cm3 of the potassium hydroxide solution to neutralise 20.0 cm 3 of tartaric acid. Calculate the concentration, in mol /
dm3, of the tartaric acid solution. (3)

(iii) Tartaric acid is purified by recrystallisation.

On analysis, 8.00 g of impure tartaric acid was found to contain 7.40 g of pure tartaric acid. Calculate the percentage purity of the
impure tartaric acid. (1)

42. Ethanol can be made both by fermentation and by the addition of steam to ethene.

(a) (i) Name the organic compound required for fermentation. (1)

(ii) State the conditions under which fermentation most readily takes place. (2)

(b) Write an equation for the reaction between steam and ethene. (1)

(c) Ethanol, C2H5OH, reacts with ethanoic acid, CH3COOH.

CH3COOH + C2H5OH → CH3COOC2H5 + H2O

(i) Name the compound CH3COOC2H5. (1)

(ii) What name is given to this type of chemical reaction? (1)

(d) (i) Name the third member of the alcohol homologous series. (1)

(ii) Draw the structural formula of this compound, showing all atoms and bonds. (1)

(b) Chlorine is used to make chloroethene.

The structure of chloroethene is shown below.

21
(i) Draw the structure of the polymer poly(chloroethene).

(iii) Complete the equation for cracking decane, C10H22.

C10H22 → C2H4 + .................

(1)

43. (a) An unsaturated compound X has the following percentage composition by mass.

C = 38.4% H = 4.8% Cl = 56.8%

(i) Show that the empirical formula is C2H3Cl. (2)

(ii) The relative molecular mass is 62.5. Use this to determine the molecular formula of X. (1)

(iii) Draw the displayed formula for X. (1)

(iv) Draw a section of the polymer chain formed if X were to be polymerised. (1)

(v) State three conditions used in industry in the polymerisation of an alkene. (3)

(b) A section of a polymer chain is shown below. Write the structural formulae of the two monomers.

−OC (CH2)4 CO.NH (CH2)6 NH −

Monomer 1

Monomer 2

(2)

44. (a) State what is meant by structural isomerism. (2)

(b) Draw the structural formulae for the two alcohols with the molecular formula C3H8O.

(2)

(c) Three isomers A, B and C have the molecular formula C3H6O2. When A is added to aqueous sodium carbonate, carbon dioxide is
evolved. B and C are esters.

(i) Give a test to identify carbon dioxide. (1)

(ii) What does the liberation of carbon dioxide indicate about the class of compound to which A belongs? Write the structural
formula for A showing the bonding in the functional group.

Class of compound__________________________________________________________________________________________
Structural formula

(2)

(iii) Write the structural formulae for the two esters B and C showing the bonding in the functional group. Name one of the esters.

(3)

GOOD LUCK

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