organic chemistry - bishop wordsworth's school · specification points year 10 – organic...
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Specification Points
Year 10 – Organic Chemistry
Crude oil, hydrocarbons and alkanes Crude oil is a finite resource found in rocks made from the remains of an ancient biomass, mainly plankton that was buried in mud. Crude oil is a mixture of a very large number of compounds, mainly hydrocarbons (molecules made of hydrogen and carbon only). Most of the hydrocarbons in crude oil are hydrocarbons called alkanes. Alkanes are a homologous series with a general formula of CnH2n+2 The first four members of the alkanes are methane, ethane, propane and butane. Alkane molecules can be represented in the following forms: C2H6 or structural formula.
Fractional distillation and petrochemicals Hydrocarbons in crude oil can be separated into fractions by fractional distillation by evaporating the oil and allowing it to condense at different temperatures. Fractions contain molecules with a similar number of carbon atoms. The fractions are processed to produce fuels and feedstock for the petrochemical industry. Many of the fuels on which we depend for our modern lifestyle, such as petrol, diesel oil, kerosene, heavy fuel oil and liquefied petroleum gases, are produced from crude oil. Many useful materials on which modern life depends are produced by the petrochemical industry, such as solvents, lubricants, polymers, detergents.
Properties of hydrocarbons Some properties of hydrocarbons depend on the size of their molecules, including boiling point and viscosity which increase with increasing molecular size and flammability which decreases with increasing molecular size. These properties influence how hydrocarbons are used as fuels. During combustion, the carbon and hydrogen in the fuels are oxidised. The complete combustion of a hydrocarbon produces carbon dioxide and water and energy. Students should be able to write balanced equations for the complete combustion of hydrocarbons with a given formula. Knowledge of trends in properties of hydrocarbons is limited to boiling points, viscosity and flammability.
Cracking and alkenes Hydrocarbons can be broken down (cracked) to produce smaller, more useful molecules. This process involves heating the hydrocarbons to vaporise them. The vapours are either passed over a hot catalyst or mixed with steam and heated to a very high temperature so that thermal decomposition reactions then occur. Be able to balance cracking equations. The products of cracking include alkanes and another type of hydrocarbon called alkenes. Alkenes are more reactive than alkanes and react with bromine water, turning it from orange to colourless. Cracking produces small molecules which have high demand for use in fuels. Alkenes are used to make polymers and as starting material to make many other chemicals.
Organic Chemistry
Structure and formulae of alkenes Alkenes are hydrocarbons with a double carbon to carbon bond. The general formula for the homologous series of alkenes is CnH2n Alkenes are unsaturated, they have two fewer hydrogen atoms than the comparable alkane The first 4 members of the homologous series are ethene, propene, butene and pentene. Alkene molecules can be represented in the following forms: C3H6 or structural formulae.
Reactions of alkenes Alkenes are hydrocarbons with the functional group C=C. Alkenes react with oxygen in combustion reactions in the same way as other hydrocarbons, but they tend to burn in air with smoky flames because of incomplete combustion. Alkenes react with hydrogen, water and the halogens, by the addition of atoms across the carbon-carbon double bond so that the double bond becomes a single carbon-carbon bond. The addition of hydrogen to an alkene (unsaturated) takes place in the presence of a catalyst to produce the corresponding alkane (saturated). The addition of water to an alkene takes place by reaction with steam in the presence of a catalyst to produce an alcohol. Addition of a halogen to an alkene produces a saturated compound with two halogen atoms in the molecule, eg: ethene reacts with bromine to produce dibromoethane. Students should be able to draw fully displayed structural formulae of the first four members of the alkenes and the products of their addition reactions with hydrogen, water, chlorine, bromine and iodine.
Polymers Polymers have very large molecules. The atoms in the polymer molecules are linked to other atoms by strong covalent bonds. The intermolecular forces between polymer molecules are relatively strong and so these substances are solids at room temperature.
Addition polymerisation Alkenes can be used to make polymers such as poly(ethene) and poly(propene) by addition polymerisation. In addition polymerisation reactions, many small molecules (monomers) join together to form very large molecules (polymers). Students should be able to: • recognise addition polymers and monomers from diagrams in the forms shown and
from the presence of the functional group C=C in the monomers • draw diagrams to represent the formation of a polymer from a given alkene monomer • relate the repeating unit to the monomer.
Ceramics, polymers and composites Most of the glass we use is soda-lime glass, made by heating a mixture of sand, sodium carbonate and limestone. Borosilicate glass, made from sand and boron trioxide, melts at higher temperatures than soda-lime glass. Clay ceramics (pottery and bricks) are made by shaping wet clay and then heating in a furnace. The properties of polymers depend on what monomers they are made from and the conditions under which they are made. For example, low density (LD) and high density (HD) poly(ethene) are produced from ethene using different catalysts and reaction conditions. Thermosoftening polymers consist of individual, tangled polymer chains and melt when
they are heated. Thermosetting polymers consist of polymer chains with cross-links between them and so they do not melt when they are heated. Most composites are made of two materials, a matrix or binder surrounding and binding together fibres or fragments of the other material, which is called the reinforcement. Examples of composites include wood, concrete and fibreglass. Some advanced composites are made using carbon fibres or carbon nanotubes instead of glass fibres. Students should be able to, given appropriate information: • compare quantitatively the physical properties of glass and clay ceramics, polymers,
composites and metals • explain how the properties of materials are related to their uses and select
appropriate materials.
Independent Study suggestions
1. Look at the specification points above – use the textbook pages, first edition (238-247) and second edition 244-254) or the revision guide pages (150-151) to make a few notes/spider diagram/revision cards
2. Have a go at the questions in the revision guide on pages 153-156
3. Watch the Fuse School short 3-4 minute explanation videos on any area you need extra help with:
Coal, oil and gas: https://www.fuseschool.org/topics/59/contents/828
Fractional distillation: https://www.fuseschool.org/topics/59/contents/269
Uses of crude oil fractions: https://www.fuseschool.org/topics/59/contents/830
Functional groups: https://www.fuseschool.org/topics/59/contents/270
Formulae of organic compounds: https://www.fuseschool.org/topics/59/contents/268
Alkanes and Alkenes: https://www.fuseschool.org/topics/59/contents/233
Complete and incomplete combustion: https://www.fuseschool.org/topics/65/contents/330
Isomers: https://www.fuseschool.org/topics/59/contents/1198
Cracking: https://www.fuseschool.org/topics/59/contents/273
Alkenes and bromine water: https://www.fuseschool.org/topics/59/contents/829
Halogenation: https://www.fuseschool.org/topics/59/contents/883
Polymers: https://www.fuseschool.org/topics/59/contents/1000
Making polyethene: https://www.fuseschool.org/topics/59/contents/943
Polymers from chloroethene an propene https://www.fuseschool.org/topics/59/contents/279
Thermosetting polymers: https://www.fuseschool.org/topics/59/contents/972
4. You might not want to have a go at the past paper questions which follow which you can mark with the markscheme.
Q1.This question is about organic compounds.
Hydrocarbons can be cracked to produce smaller molecules.
The equation shows the reaction for a hydrocarbon, C18H38
C18H38 → C6H14 + C4H8 + 2 C3H6 + C2H4
(a) Which product of the reaction shown is an alkane?
Tick one box.
C2H4
C3H6
C4H8
C6H14
(1)
(b) The table below shows the boiling point, flammability and viscosity of C18H38 compared with the other hydrocarbons shown in the equation.
Boiling point Flammability Viscosity
A highest lowest highest
B highest lowest lowest
C lowest highest highest
D lowest highest lowest
Which letter, A, B, C or D, shows how the properties of C18H38 compare with the properties of C2H4, C3H6, C4H8 and C6H14?
Tick one box.
A
B
C
D
(1)
(c) The hydrocarbon C4H8 was burnt in air.
Incomplete combustion occurred.
Which equation, A, B, C or D, correctly represents the incomplete combustion reaction?
A C4H8 + 4O → 4CO + 4H2
B C4H8 + 4O2 → 4CO + 4H2O
C C4H8 + 6O2 → 4CO2 + 4H2O
D C4H8 + 8O → 4CO2 + 4H2
Tick one box.
A
B
C
D
(1)
Q2.This question is about hydrocarbons.
(a) Most of the hydrocarbons in crude oil are alkanes.
(i) Large alkane molecules can be cracked to produce more useful molecules.
The equation shows the cracking of dodecane.
Give two conditions used to crack large alkane molecules.
1 ................................................................................................................
2 ................................................................................................................ (2)
(ii) The products hexene and ethene are alkenes.
Complete the sentence.
When alkenes react with bromine water the colour changes from orange to .................................................. .
(1)
(iii) Butane (C4H10) is an alkane.
Complete the displayed structure of butane.
(1)
(b) A group of students investigated the energy released by the combustion of four hydrocarbon fuels.
The diagram below shows the apparatus used.
Each hydrocarbon fuel was burned for two minutes.
Table 1 shows the students’ results.
Table 1
After two minutes
Name and formula of hydrocarbon fuel
Mass of fuel used
in g
Temperature increase of water in °C
Energy released by fuel in
kJ
Energy released
by 1.0 g of fuel in kJ
Relative amount of smoke in the flame
Hexane, C6H14 0.81 40 16.80 20.74 very little smoke
Octane, C8H18 1.10 54 22.68 20.62 some smoke
Decane, C10H22
1.20 58 24.36 smoky
Dodecane, C12H26
1.41 67 28.14 19.96 very smoky
(i) Calculate the energy released by 1.0 g of decane in kJ.
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Energy released = ...................................... kJ (2)
(ii) Suggest one improvement to the apparatus, or the use of the apparatus, that would make the temperature increase of the water for each fuel more accurate.
Give a reason why this is an improvement.
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................................................................................................................... (2)
(iii) The students noticed that the bottom of the beaker became covered in a black substance when burning these fuels.
Name this black substance.
Suggest why it is produced.
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(iv) A student concluded that hexane is the best of the four fuels.
Give two reasons why the results in Table 2 support this conclusion.
1 ................................................................................................................
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2 ................................................................................................................
................................................................................................................... (2)
(c) In this question you will be assessed on using good English, organising information clearly and using specialist terms where appropriate.
Most car engines use petrol as a fuel.
• Petrol is produced from the fractional distillation of crude oil.
• Crude oil is a mixture of hydrocarbons.
• Sulfur is an impurity in crude oil.
Car engines could be developed to burn hydrogen as a fuel.
• Hydrogen is produced from natural gas.
• Natural gas is mainly methane.
Table 2 shows information about petrol and hydrogen.
Table 2
Petrol Hydrogen
State of fuel at room
temperature Liquid Gas
Word equation for
combustion of the fuel petrol + oxygen → carbon
dioxide + water
hydrogen + oxygen →
water
Energy released from
combustion of 1 g of the fuel
47 kJ 142 kJ
Describe the advantages and disadvantages of using hydrogen instead of petrol in car engines.
Use the information given and your knowledge and understanding to answer this question. (6)
(Total 18 marks)
Q3.A student investigated the viscosity of liquid hydrocarbons.
A viscous liquid is a liquid that flows slowly.
The student used this method.
• Measure 50 cm3 of the liquid hydrocarbon.
• Pour the liquid hydrocarbon into the funnel, as shown in Figure 1.
• Time how long it takes for all of the liquid hydrocarbon to run out of the funnel.
• Repeat the experiment for other liquid hydrocarbons.
(a) (i) Give the name of apparatus A in Figure 1.
............................................................................................................... (1)
(ii) Name the apparatus that could be used to measure 50 cm3 of liquid hydrocarbon.
............................................................................................................... (1)
(b) The student’s results for six liquid hydrocarbons are shown in Table 1.
Table 1
Formula of liquid hydrocarbon
Time for liquid hydrocarbon to run out of the funnel in seconds Mean time in
seconds Experiment 1 Experiment 2 Experiment 3
C5H12 12 11 13 12
C6H14 14 15 15 15
C7H16 19 20 18
C8H18 27 26 28 27
C10H22 46 48
47
C12H26 65 67 69 67
(i) The student did the experiment three times with each liquid hydrocarbon.
Give two reasons why.
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............................................................................................................... (2)
(ii) Use the data in Table 1 to calculate the mean time, in seconds, for C7H16
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Mean time = ................................... seconds (1)
(iii) Complete the sentence.
As the number of carbon atoms in a molecule of liquid hydrocarbon increases, the time taken for the liquid hydrocarbon to run out of the funnel ................................................ .
(1)
(iv) A ring has been drawn around one result in Table 1.
This result has not been used to calculate the mean time for C10H22
Suggest why this result was not used.
...............................................................................................................
............................................................................................................... (1)
(v) Suggest one error the student may have made to get the ringed result.
...............................................................................................................
...............................................................................................................
............................................................................................................... (1)
(c) The student investigated the effect of temperature on the viscosity of one of the liquid hydrocarbons.
The liquid hydrocarbon he was using had the hazard symbols shown in Figure 2.
(i) Suggest why the student warmed the liquid hydrocarbon using warm water and not a Bunsen flame.
...............................................................................................................
............................................................................................................... (1)
(ii) The student wore safety glasses.
Give one other safety precaution the student should take, and give a reason for this safety precaution.
Safety precaution .................................................................................
Reason .................................................................................................
............................................................................................................... (2)
(d) This is the method the student used to investigate the effect of temperature on the viscosity of one of the liquid hydrocarbons.
• Measure 50 cm3 of the liquid hydrocarbon and pour it into a beaker.
• Stand the beaker of liquid hydrocarbon in a heated water bath.
• Leave for a few minutes.
• Measure the temperature of the liquid hydrocarbon.
• Pour the liquid hydrocarbon into the funnel, as shown in Figure 3.
• Time how long it takes for all of the liquid hydrocarbon to run out of the funnel.
• Repeat the experiment at different temperatures.
(i) The student’s results are shown in Table 2.
Table 2
Temperature of liquid
hydrocarbon in °C Time to run out of the
funnel in seconds
23 27
30 21
37 17
46 16
55 11
65 9
Plot the results shown in Table 2 on the graph in Figure 4.
Draw a curve of best fit.
(3)
(ii) One of the points is anomalous.
Draw a ring around the anomalous point on your graph. (1)
(iii) Predict how long it will take the liquid hydrocarbon to run through the funnel at 70 °C.
Show your working on your graph.
Time = ........................................ seconds
(2)
(iv) Describe the relationship between the temperature of the liquid hydrocarbon and the viscosity of the liquid hydrocarbon.
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............................................................................................................... (3)
(v) The apparatus the student used in Figure 2 could lead to a systematic error in the results. Identify one source of systematic error, and describe how the student could avoid or reduce the error.
...............................................................................................................
...............................................................................................................
...............................................................................................................
............................................................................................................... (2)
(Total 22 marks)
Q4. Crude oil is a mixture of mostly alkanes.
(a) Crude oil is separated into useful fractions by fractional distillation.
(i) Describe and explain how the mixture of alkanes is separated by fractional distillation.
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.......................................................................................................................... (3)
(ii) The table gives the name and formula for each of the first three alkanes.
Complete the table to show the formula of butane.
Name of alkane Formula
Methane CH4
Ethane C2H6
Propane C3H8
Butane
(1)
(b) The structural formula of methane, CH4, is:
H │ H │ H
Draw the structural formula of propane, C3H8
(1)
(c) The relative amounts of and the market demand for some hydrocarbons from the fractional distillation of crude oil are shown in the graph.
(i) Why is the market demand for the C5 – C8 fraction higher than the market demand for the C21 – C24 fraction?
..........................................................................................................................
.......................................................................................................................... (1)
(ii) Cracking is used to break down large hydrocarbon molecules into smaller hydrocarbon molecules.
Complete the symbol equation by writing in the formula of the other hydrocarbon.
C20H42 C16H34 + 2 .......................................... (1)
(iii) The C5 – C8 fraction has low supply and high market demand.
Suggest three ways in which the oil industry could overcome this problem.
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3 .......................................................................................................................
.......................................................................................................................... (3)
(Total 10 marks)
Q5. To make a plastic, such as poly(ethene), from crude oil involves many processes.
(a) Describe how crude oil is separated into fractions.
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........................................................................................................................ (2)
(b) Ethene is produced by cracking the hydrocarbons in the naphtha fraction.
(i) Balance the symbol equation for this reaction.
C10H22
decane → C4H10
butane + C2H4
ethene
(1)
(ii) Describe how cracking is carried out.
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...............................................................................................................
............................................................................................................... (2)
(c) Alkanes, such as butane (C4H10), do not form polymers.
Alkenes, such as ethene (C2H4), do form polymers.
Explain these statements.
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........................................................................................................................ (2)
(d) Ethene molecules form the polymer poly(ethene). One molecule in poly(ethene) will contain thousands of carbon atoms. The diagram represents part of a poly(ethene) molecule.
Propene molecules form the polymer poly(propene).
Draw a diagram to represent part of a poly(propene) molecule.
(2)
(Total 9 marks)
Answers:
M1.(a) C6H14
1
(b) A 1
(c) B 1
M2.(a) (i) high temperature
allow heating / hot / 250-900 °C 1
catalyst or steam
allow named catalyst eg zeolite, Al2O3, silica, ceramic
allow in the absence of air / oxygen 1
ignore any references to pressure
(ii) colourless
allow decolourised
ignore clear / discoloured 1
(iii) 1
(b) (i) 20.3(0) (kJ)
if answer incorrect allow 1 mark for 24.36/1.2 2
(ii) use a lid
allow insulate beaker or use draught shield 1
reduce energy / heat loss
ignore references to thermometer or repeats or distance of flame or loss of water vapour
allow stir (1) to distribute energy / heat (1)
allow use a metal can (1) as it’s a better conductor (1) 1
(iii) carbon/soot
ignore tar, smoke 1
(produced by) incomplete combustion
allow from a limited supply of oxygen/air 1
(iv) hexane gives out the greatest energy (per 1.0 g)
ignore more energy 1
hexane produces the least smoke / carbon / soot
allow has the cleanest flame
ignore less smoke / carbon / soot 1
(c) Marks awarded for this answer will be determined by the Quality of Written Communication (QWC) as well as the standard of the scientific response. Examiners should also apply a ‘best-fit’ approach to the marking.
Level 3 (5 – 6 marks): Descriptions of advantages and disadvantages that are linked to their own knowledge.
Level 2 (3 – 4 marks): Descriptions of an advantage and a disadvantage with some use of their knowledge to add value.
Level 1 (1 – 2 marks): Statements made from the information that indicate whether at least one statement is an advantage or a disadvantage or a linked advantage or disadvantage
0 marks: No relevant content
Examples of the added value statements and links made in the response could include: Note that link words are in bold; links can be either way round. Accept reverse arguments and ignore cost throughout.
Advantages of using hydrogen: • Combustion only produces water so causes no pollution • Combustion does not produce carbon dioxide so this does not contribute to global warming or climate change • Combustion does not produce sulfur dioxide so this does not contribute to acid rain • Incomplete combustion of petrol produces carbon monoxide that is toxic • Incomplete combustion of petrol produces particulates that contribute to global dimming • Petrol comes from a non-renewable resource but there are renewable/other methods of producing hydrogen • Hydrogen releases more energy so less fuel needed or more efficient
Disadvantages of using hydrogen: • Hydrogen is a gas so is difficult to store or transfer to vehicles • Hydrogen gas is very flammable so leaks cause a greater risk of explosion • Most hydrogen is produced from fossil fuels which are running out • Cannot be used in existing car engines so modification / development or replacement is needed • Lack of filling stations so difficult to refuel your vehicle
6
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M3.(a) (i) (conical) flask 1
(ii) measuring cylinder / pipette / burette 1
(b) (i) any two from: • so anomalous results could be identified / ignored • so a mean / average could be taken • (to improve) accuracy
2
(ii) 19 1
(iii) increases / gets longer / gets bigger 1
(iv) anomalous / does not agree with other times for C10H22
1
(v) any one from: • shorter hydrocarbon used • volume of hydrocarbon too small • started timing late • stopped timing too early / when liquid left in funnel
must suggest why the result is lower than the others.
allow the temperature was higher or the students used a wider funnel. 1
(c) (i) flammable 1
(ii) suitable safety precaution 1
reason that links the safety precaution to the hazard symbols
eg:
• wear gloves
• (because) it is hazardous to health / harmful / toxic / irritant
or
• do not pour down sink or dispose of properly
• (because) it is harmful to the environment / kills fish
or
• wear a mask or do it in the fume cupboard or a well-ventilated area
• respiratory irritant 1
(d) (i) points plotted correctly (within half small square)
all six points correct scores 2
3, 4 or 5 points correct scores 1 2
smooth curve of best fit 1
(ii) point at 46 °C circled
allow point furthest from the line as drawn 1
(iii) working shown on graph 1
value read from graph line drawn (within half small square) 1
(iv) the higher the temperature the lower the viscosity
allow the higher the temperature the lower / shorter the time taken for 1 mark 2
non-linear or change gets smaller as temperature gets higher
answer relating temperature to time taken can score a maximum of 2 marks. 1
(v) identifying source of the error 1
method of avoiding the error
eg:
• the temperature will drop
• insulate the funnel
or
• runs out before all added
• put a tap on the funnel 1
[22]
M4. (a) (i) heat / evaporate the crude oil / change to gas or vapour
do not accept heat with catalyst 1
cool / condense (hydrocarbons)
allow small molecules at top and / or large molecules at bottom 1
at different temperatures / boiling points
if the answer describes cracking ‘ no marks 1
(ii) C4H10
1
(b) H H H │ │ │ H ─C ─ C ─ C ─ H │ │ │ H H H
1
(c) (i) C5 to C8 fraction are fuels or easier to burn or petrol (fraction)
accept C21 to C24 fraction not useful as fuels
do not accept produce more energy 1
(ii) C2H4
do not accept C4H8
1
(iii) any three from:
• use different / lighter crude oils
• develop markets for low demand fractions
• develop new techniques / equipment to use low demand fractions as fuels
• cracking
• convert low demand fractions to high demand fractions or bigger molecules to smaller molecules
• develop alternative / bio fuels
do not accept price 3
[10]
M5. (a) vaporise / evaporate
allow boil for vaporise 1
different condensing points / temperatures
accept condense at different levels
ignore different size molecules or different densities
mention of cracking = max 1
allow boils at different temperatures and condenses for 2 marks
if no other marks awarded allow
fractional distillation for 1 mark 1
(b) (i) 3 (C2H4)
accept +C4H8
1
(ii) (decane / naphtha / hydrocarbon) vaporise / evaporate
allow crude oil
allow boil for vaporise
1
(passed over) a catalyst / alumina / porous pot
ignore other names of catalysts 1
(c) any two from:
‘they’ must be clarified
• alkanes / butane (molecules) do not have a (carbon carbon) double bond / are saturated / have (carbon carbon) single bonds
• alkenes / ethene (molecules) have (carbon carbon) double bonds
or are unsaturated
• alkenes / ethene molecules are able to bond to other molecules 2
(d) single bonds between carbon atoms
– C - C – 1
the -CH3 group appears on each pair of carbons on the ‘chain’
NB any double bonds = 0 marks 1
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