26

Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.

This document may have been altered from the original.
What you do
Work in pairs or small groups so that you can discuss the task with other
students.
You will be provided with a set of cards showing the names of some nylons and
the structures of the monomers and repeating units of the polymers involved.
1 Your task is to sort the cards into sets so that a name, structure(s) of the
monomer(s) and polymer repeating units all refer to the same nylon.
2 When you have sorted out the cards, place them in lines to show:
nylon name monomer(s) structure(s) polymer repeating unit structure
3 Check with your teacher that you have correctly sorted out the cards. If not,
think about how they might be rearranged.
4 Make a copy of the names and structures to use for revision.
A nylon is made from its monomers by
condensation polymerisation. In this activity
you will match together the names of nylons
with the structures of their monomers and the
repeating units of the polymers.
NamiNg NyloNs
mR2.1
setofcardsshowingnamesofnylons,structuresofmonomersandstructuresofpolymerrepeatingunits
Requirements
H
2
N(CH
2
)
2
NH
2
H
2
N(CH
2
)
6
NH
2
H
2
N(CH
2
)
5
NH
2
H
2
N(CH
2
)
10
COOH
HOOC(CH
2
)
2
COOH ClOC(CH
2
)
4
COCl
HOOC(CH
2
)
8
COOH
(NH(CH
2
)
2
NHCO(CH
2
)
2
CO)
(NH(CH
2
)
6
NHCO(CH
2
)
4
CO)
(NH(CH
2
)
5
NHCO(CH
2
)
8
CO)
(NH(CH
2
)
10
CO)
Nylon-6,6
Nylon-2,4
Nylon-5,10
Nylon-11
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Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
This document may have been altered from the original.
Naming nylons mR2.1
H
2
N(CH
2
)
2
NH
2
H
2
N(CH
2
)
6
NH
2
H
2
N(CH
2
)
5
NH
2
H
2
N(CH
2
)
10
COOH
HOOC(CH
2
)
2
COOH ClOC(CH
2
)
4
COCl
HOOC(CH
2
)
8
COOH
(NH(CH
2
)
2
NHCO(CH
2
)
2
CO)
(NH(CH
2
)
6
NHCO(CH
2
)
4
CO)
(NH(CH
2
)
5
NHCO(CH
2
)
8
CO)
(NH(CH
2
)
10
CO)
Nylon-6,6
Nylon-2,4
Nylon-5,10
Nylon-11
252_02-MR_SAC A2 SP.indd 27 17/3/09 08:27:51
28
Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
This document may have been altered from the original.
What you do
1 Pour about 1 cm
3
of the 1,6-diaminohexane solution into a 5 cm
3
beaker.
2 Carefully add an equal volume of the decanedioyl dichloride solution to the
beaker. Two separate layers will form. Do not mix them.
3 Where the two layers are in contact, a nylon flm forms. Use a pair of
tweezers to slowly pull out the nylon and hook the nylon thread onto a
glass rod or a test tube.
4 Slowly wind the thread around the glass rod. As the nylon is removed, more
forms at the solution interface, so you should be able to keep winding for
some time.
5 Once you have made some nylon it needs to be washed thoroughly with tap
water. Take care not to touch the nylon because it forms as a hollow tube,
and there will still be some chemicals trapped in the middle of it.
A nylon is made from its monomers by
condensation polymerisation. You may already
have done this or a similar experiment in an
earlier course. If so, you can omit this activity
and go on to Activity MR2.3.
makiNg NyloN
mR2.2
accesstoafumecupboard
5cm
3
beaker
glassrodortesttube
tweezers
protectivegloves
decanedioyldichloride,35%solutionincyclohexane(1cm
3
)
1,6-diaminohexanesolution,35%aqueoussolution(1cm
3
)
CARE Decanedioyl dichloride has an irritating vapour that is a
powerful lachrymator (eye irritant) and this effect is often delayed.
Work in a fume cupboard or a well-ventilated laboratory.
Requirements
WEAR EYE
PROTECTION
CaRE Eye protection
(goggles) and gloves must
be worn.
WEAR GLOVES
HARMFUL
decanedioyl chloride in
cyclohexane solution
HIGHLY
FLAMMABLE
Questions
1 What is the name of the nylon you have made? 2 Write out an equation to show the formation of this nylon.
252_02-MR_SAC A2 SP.indd 28 17/3/09 08:27:52
29
Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
This document may have been altered from the original.
Introduction
If you did Activity MR2.2 you will have made a nylon from its monomers by
condensation polymerisation. A reaction like this, in which a new substance is
made from simpler substances, is called a synthesis.
The reverse process, in which a large molecule is broken down into simpler
molecules, is called degradation. This type of reaction is often used by chemists to
fnd out about the composition of substances. If they can identify the degradation
products, they may be able to work out the structure of the original compound.
The amide linkages in nylon can be hydrolysed (split by water) to give the
parent di-acid and di-amine. The reaction with water is very slow indeed, but it can
be speeded up by carrying out the hydrolysis in acid solution (acid hydrolysis).
You will use moderately concentrated sulfuric(VI) acid (about 5.5 mol dm
3
) for the
hydrolysis.
What you do
Part 1: Breaking down the nylon
1 Place 2 g of nylon-6,6 granules into a 100 cm
3
fask to which a refux
condenser can be attached.
2 Pour 35 cm
3
of 5 mol dm
3
sulfuric(VI) acid into the fask. (CARE Sulfuric acid of
this concentration is very corrosive.) Fit the condenser to the fask (Figure 1).
3 Place the reaction fask and condenser in the heating mantle. Heat the
reaction mixture under refux for about 3 hours. (This technique is used
when you want to heat reactants for some time, but not lose either the
reactants or the products by evaporation.) Add a few anti-bumping granules
(boiling chips) to help the mixture boil smoothly.
The nylon will all have dissolved after about 45 minutes, but you should carry on
heating to complete the degradation.
4 Allow the fask and contents to cool, place them in an ice bath and leave
overnight for crystals to form.
5 Collect the crystals of hexanedioic acid by vacuum fltration. Keep the
fltrate for use later.
In this experiment you are going to convert
some nylon-6,6 polymer back into its original
di-acid and di-amine. The linkages in the nylon
are broken down by hydrolysis using sulfuric
acid. This activity will allow you to improve
your skill in carrying out an organic reaction
safely. You will learn how to purify an organic
solid by recrystallisation and how to measure
its melting point.
TakiNg NyloN
apaRT
mR2.3
electricheatingmantle
melting-point apparatus for use up to 150 C
thin-walled capillary tubes (or melting-point tubes)
apparatus for vacuum (suction) fltration
100 cm
3
boiling fask (e.g. round-bottomed fask)
Liebig condenser
250 cm
3
conical fasks (2)
100 cm
3
measuring cylinder
10 cm
3
measuring cylinder
250 cm
3
beakers (2)
watch glass
anti-bumping granules (boiling chips)
nylon-6,6 granules (2 g)
sulfuric(VI) acid, approximately 5 mol dm
3
(35 cm
3
)
saturated sodium hydrogencarbonate solution (20 cm
3
)
sodium hydroxide solution, 2 mol dm
3
(5 cm
3
)
ice
universal indicator paper
CARE Sulfuric acid of this concentration is very corrosive.
Requirements
WEAR EYE
PROTECTION
CaRE Eye protection (goggles)
must be worn throughout.
sodium hydroxide solution
CORROSIVE
sulfuric(Vi) acid
CORROSIVE
Coudeuse|
hy|ou-G,G
g|auu|es +
su|lu||c(Vl) ac|d
wale| |u
wale| oul
hEAT
Figure 1 Breaking down the nylon.
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Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
This document may have been altered from the original.
mR2.3 Taking nylon apart
Part 2: Purifying the hexanedioic acid by recrystallisation
Your solid now needs to be purifed by recrystallisation.
6 Place your hexanedioic acid crystals in a 250 cm
3
conical fask. Add 10 cm
3
of
distilled water. Hold the neck of the fask with an insulating holder and
gently heat the fask, swirling the contents at the same time. If some crystals
remain when the water starts to boil, add a further 5 cm
3
of water and reheat.
7 Carry on in this way until all the crystals have dissolved in the minimum
quantity of water.
8 If your solution is clear, you can loosely cover the opening to the fask and
leave the solution to cool overnight.
If the solution contains debris, this can be removed by carefully decanting
most of the solution into a second fask, leaving the debris behind. You will
need to reheat the solution to redissolve the crystals before covering it and
leaving it to recrystallise.
9 Collect the crystals by vacuum fltration and leave them to dry on a watch
glass. To speed things up you can place the watch glass in an oven or on a
food-warming tray.
Part 3: Finding a melting point
Hexanedioic acid melts at 153 C. Find the melting point of your crystals and
compare it with this value.
This is what you do to determine a melting point.
10 Carefullyheatoneendofasmallthin-walledcapillarytubeamelting-point
tubesothattheopeningisjustsealed.Leavethetubetocool.
11 Grind a small quantity of your dry crystals in one corner of the watch glass
until you have a fne powder. Tap the open end of the melting-point tube
into the fne powder so that a little powder packs into the tube. Invert the
tube and tap it gently so that the powder falls to the closed end. Your
teacher may show you an effective way of doing this. Do not try to put too
much powder into the tube at once.
12 Repeattheprocedureuntilyouhaveabout0.51cmdepthofpowderinthe
tube. You may have an electrically heated melting-point apparatus that your
teacher will show you how to use. Another type of melting point apparatus is
shownbelowifyouareusingoneofthese,steps13 and 14 describe how
to use it.
*URRYHWRDOORZ
DLULQDQGRXWRI
WKHDSSDUDWXV
7KHUPRPHWHU
0HOWLQJSRLQWWXEH
5XEEHUEDQG
6XLWDEOHOLTXLG
+($7
13 Fix the tube into position in the melting-point apparatus as shown in
Figure 2.
14 Slowly heat the side-arm of the apparatus with a very low Bunsen burner
fame. The design of the apparatus should ensure a circulation of warm
liquid around the sample and thermometer. Watch the sample carefully.
When it melts, the powder will collapse into a sticky liquid. Record the
temperature at which this happens.
Figure 2 Melting-point apparatus.
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Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
This document may have been altered from the original.
15 This will be a rough value for the melting point, because you were heating it
quite quickly. To determine an accurate melting point, allow the apparatus
tocooldowntoabout10Cbelowthevalueyouhavejustrecorded.Prepare
another sample while this is happening. Then repeat the process with the
fresh sample and at a slower rate of heating.
16 Record the accurately determined melting point of your hexanedioic acid.
Part 4: Detecting the 1,6-diaminohexane produced
The diamine is still in solution in the fltrate obtained in Part 1, because it has
formed a soluble salt by reacting with the sulfuric(VI) acid.
17 Take 5 cm
3
of the fltrate and carefully pour it into 20 cm
3
of saturated sodium
hydrogencarbonate solution in a 250 cm
3
beaker. (CARE Do not add the
fltrate all in one go or the mixture will fzz dangerously.)
18 Use pH paper to make sure that the mixture is no longer acidic. If necessary
add some more sodium hydrogencarbonate solution to achieve this.
19 Then add 5 cm
3
of 2 mol dm
3
sodium hydroxide solution to make the
solution alkaline. Gently swirl the contents of the beaker and cautiously note
the smell of the solution, which contains 1,6-diaminohexane. (For
comparison, the trivial names of 1,4-diaminobutane and 1,5-diaminopentane
are putrescine and cadavarine respectively, both of which are associated with
the putrefaction of proteins in fesh.)
Taking nylon apart mR2.3
Questions
1 What property of hexanedioic acid is made use of in the
recrystallisation process?
2 Explain why recrystallisation should produce a purer
product.
3 Melting points are often used to identify compounds. They
are also a good indication of the purity of a compound. Was
your sample of hexanedioic acid pure? Explain your answer.
4 Write an equation for the hydrolysis of a short section of
nylon-6,6 to produce hexanedioic acid and
1,6-diaminohexane.
252_02-MR_SAC A2 SP.indd 31 17/3/09 08:27:53
32
Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
This document may have been altered from the original.
What you do
A series of tests on butylamine, an example of an amine, are listed below. Before
you start, read through all the tests and draw up a suitable table in which to
record your observations.
Test 1: Solubility
a Add a few drops of butylamine to 1 cm depth of water in a test tube.
b Test and record the pH of any solution that has been formed. Save the
mixture for the next test.
Test 2: Adding acid and alkali
a Add a few drops of concentrated hydrochloric acid to the butylamine solution
from Test 1.
b Make a note of any changes, including smell, before and after addition of the
acid.
c Now add about 2 cm depth of 2 mol dm
3
sodium hydroxide solution and
shake the tube gently; again, note any changes.
Test 3: Adding ethanoyl chloride
a Place 10 drops of butylamine in a clean, dry test tube.
b Add 10 drops, one drop at a time, of ethanoyl chloride (CARE Can react
violently) and make a note of your observations. Save your tube for the next
test.
Test 4: Hydrolysing an amide
a To the tube from Test 3, which contains a secondary amide, add 1 cm depth
of water and carefully stir the mixture.
b Now add 3 cm depth of 2 mol dm
3
sodium hydroxide solution.
c Warm the mixture, and hold a piece of moistened pH paper at the mouth of
the test tube.
In this activity you will investigate the
properties of the amine, butylamine.
iNVEsTigaTiNg aN
amiNE
mR2.4
accesstoafumecupboard
testtubesandrack
butylamine(2cm
3
)
concentratedhydrochloricacid(afewdrops)
sodiumhydroxidesolution,2moldm
3
(10 cm
3
)
ethanoylchloride(2cm
3
)
universalindicatorpaper
CARE Butylamine and ethanoyl chloride are volatile and
have unpleasant, highly fammable vapours. Use the
bottles in a fume cupboard and avoid inhaling the vapours.
Requirements
WEAR EYE
PROTECTION
CaRE Eye protection
must be worn.
concentrated hydrochloric acid
CORROSIVE
sodium hydroxide solution
CORROSIVE
CORROSIVE
butylamine
HIGHLY
FLAMMABLE
CORROSIVE
ethanoyl chloride
HIGHLY
FLAMMABLE
252_02-MR_SAC A2 SP.indd 32 17/3/09 08:27:53
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Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
This document may have been altered from the original.
Investigating an amine mR2.4
Questions
Test 1: solubility
1 Is butylamine soluble in water?
2 How can you explain any solubility in terms of bonding
between particles?
3 Write an equation to explain any change to the pH of the
water.
Test 2: adding acid and alkali
4 Write equation(s) for any changes you have noted.
Test 3: adding ethanoyl chloride
5 Write an equation for any reaction that occurs resulting in
the formation of a secondary amide.
Test 4: Hydrolysing an amide
6 Write an equation for the reaction between the secondary
amide and sodium hydroxide.
7 Explain any change to the pH paper in terms of the process
occurring in the test tube.
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Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
This document may have been altered from the original.
Introduction
Liquid crystals are sometimes referred to as the fourth state of matter,
intermediate between the crystalline and liquid states. They are used to make
LCD displays in many types of electronic equipment. The molecules making up
liquid crystals have rod- or pencil-like structures. In this activity you will be
condensing two molecules together to illustrate how a liquid crystal can be
produced.
What you do
1 Working in a fume cupboard, dissolve 1 g of cholesterol in 3 cm
3
of pyridine
in a 50 cm
3
conical fask.
2 Add 0.4 cm
3
of benzoyl chloride to the fask. (CARE Benzoyl chloride is a
lachrymator and will bring tears to your eyes.)
3 Heat the mixture on a steam bath for 10 minutes. Allow the fask to cool.
4 Add 15 cm
3
of methanol to the mixture in the fask.
5 Collect the solid cholesteryl benzoate by suction fltration using a Hirsch
funnel. Use a little methanol to rinse the fask and wash the crystals.
6 To obtain high-quality crystals, recrystallise your crude product using about
15 cm
3
of ethyl ethanoate in a boiling tube (cooling in an ice bath).
7 Place your product on a watch glass and allow it to dry.
8 Test the liquid crystal properties of your product by placing a small amount
of it (approx 0.1 g) on the end of a microscope slide. Hold the slide with
tongs above a small Bunsen burner fame. Observe what happens when the
compound is gently heated. Let the compound cool down and again note
changes in the appearance of your sample.
In this activity you will make and test a
compound that shows liquid crystal properties.
makiNg a liQuid
CRysTal
mR2.5
accesstoafumecupboard
250cm
3
beaker
50cm
3
conical fask
apparatusforsettingupasteambath
apparatusforvacuumfltrationusingaHirschfunnel
boilingtube
stirringrod
watchglass
microscopeslide
tongs
cholesterol(1g)
pyridine(3cm
3
)
benzoylchloride(0.4cm
3
)
ethylethanoate(15cm
3
)
methanol(15cm
3
)
crushedice
CARE Pyridine has a harmful vapour, benzoyl chloride is
lachrymatory and methanol is toxic. Work in a fume cupboard
and avoid inhaling any vapours. Wear eye protection at all
times and disposable nitrile gloves when handling the
chemicals.
CARE Pyridine, methanol and ethyl ethanoate are all highly
fammable. Avoid naked fames.
Requirements
benzoyl chloride
CORROSIVE
WEAR EYE
PROTECTION
CaRE Eye protection and
protective gloves must be
worn.
WEAR GLOVES
HARMFUL
pyridine
HIGHLY
FLAMMABLE
ethyl ethanoate
HIGHLY
FLAMMABLE
IRRITANT
methanol
HIGHLY
FLAMMABLE
TOXIC
252_02-MR_SAC A2 SP.indd 34 17/3/09 08:27:54
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Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
This document may have been altered from the original.
Making a liquid crystal mR2.5
Questions
1 What changes in appearance of your product when it is
heated and cooled suggest that it has liquid crystal
properties?
2 The skeletal formula of cholesterol is shown opposite.
Cholesterol undergoes a condensation reaction with
benzoyl chloride to form the ester cholesteryl benzoate.
Draw out the skeletal formula of cholesteryl benzoate.
HO
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Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
This document may have been altered from the original.
What you do
Start by working on your own. Table 1 below includes simple amides and esters
as well as polyamides (nylons) and polyesters.
1 For each of the starting materials shown in Table 1, work out the structure(s)
of the product(s) formed when the ester or amide is hydrolysed under the
conditions indicated.
2 Now compare your answers with those of another student. Discuss your
answers and add to, or modify, your tables where necessary and then
compare your answers with those agreed by another pair of students. Amend
your answers where necessary.
3 Finally, check with your teacher that your answers are correct. Make a note
of any structures that you were less confdent about working out, to help
you when you come to revise this topic at a later date.
Table 1
amide or ester Reagent Hydrolysis product(s)
CH
3
CONH
2
HCl
C
2
H
5
CONH
2
NaOH
CH
3
COOC
2
H
5
HCl
HCOOCH
3
NaOH
( NH(CH
2
)
6
NHOC(CH
2
)
4
CO ) HCl
( NH(CH
2
)
5
NHOC(CH
2
)
8
CO ) NaOH
( OCH
2
CH
2
OOCC
6
H
4
CO ) HCl
( O(CH
2
)
3
OOCCO ) NaOH
( NH(CH
2
)
5
CO ) HCl
( OCH
2
CH
2
CO ) NaOH
Amides and esters can be hydrolysed using acid
or alkali. This activity will help you check that
you understand how the products of hydrolysis
depend on the conditions used.
HydRolysiNg
amidEs aNd EsTERs
mR2.6
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Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
This document may have been altered from the original.
What you do
Work with one or two other students for this activity so that you can discuss
your ideas.
You will be provided with a set of cards giving information about various aspects
of the manufacture and disposal of disposable cups made from paper and from
polystyrene.
1 Use the information on the cards to help you answer the questions that
follow. You may fnd it useful to design a table in which to summarise the
information about paper and polystyrene cups.
This activity gives you an opportunity to
compare the impact on the environment of the
manufacture and disposal of paper and plastic
disposable cups.
papER oR plasTiC?
WHiCH is
bETTER FoR THE
ENViRoNmENT?
mR3
setofinformationcards
Requirements
1
3
5
7
9
2
4
6
8
10
11
13
15
17
12
14
16
The main raw material needed to make
paper is wood, which is a renewable
resource.
However, collecting wood impacts on the
landscape trees have to be cut down both
for use as wood and to make space for
roads so that the wood can be transported.
4.1 g of petroleum is needed to make a paper
cup. 3.2 g of petroleum is needed to make a
polystyrene cup.
A paper cup weighs about 10.1 g.
A polystyrene cup weighs about 1.5 g.
A paper cup costs about 5p;a polystyrene
one costs about 2p.
Paper cups are made from bleached wood
pulp, which is made from wood chips. Only
about half of the chips are turned into pulp.
Bark and some wood waste are burned to
supply energy for the process.
In total, about 33 g of wood and bark are
used per paper cup.
To make a paper cup, chemicals such as
chlorine, sodium hydroxide, bleach,
sulfuric(VI) acid, sulfur and limestone are
needed. These chemicals are not recycled. In
total, about 1.8 g of these chemicals are
needed per cup produced.
More petroleum is needed to make a paper
cup than a polystyrene one. The wood for
paper cups has to be transported by road or
rail to the manufacturing plant.
If the cup has a wax or plastic coating, even
greater amounts of petroleum are needed
per cup.
Efficient catalysts are used to make
polystyrene, so most of the chemicals
involved (other than those from oil) can be
recycled.
Of these additional chemicals all but around
0.05 g per cup are reused in the process.
So much wood pulp is used to make a paper
cup that the whole process requires about:
12 as much steam,
36 as much electricity and
2 as much cooling water
as the process used to make a polystyrene
cup.
A polystyrene cup is made from oil.
Collecting and transporting oil can cause
environmental damage, particularly if spills
occur during drilling or transportation.
The oil (or natural gas) needed to produce
polystyrene cups is taken by pipeline to the
manufacturing plant.
Making polystyrene produces about 20 kg
of waste metal salts per tonne of
polystyrene produced.
Making paper produces about 120 kg of
waste metals per tonne of paper produced
(depending on the type of paper plant).
It is possible to reuse polystyrene cups
because they do not soak up water.
Paper cups could be reused but washing
would destroy them.
Paper cups cannot be recycled. The glues
that hold parts of the cup together cannot
be removed in the recycling process.
Plastic-coated paper is even more difficult
to recycle.
In a landfill site, paper can biodegrade
anaerobically to produce methane and carbon
dioxide in a 2:1 ratio. Paper may biodegrade
very slowly, especially in dry regions of the
world. Polystyrene does not biodegrade.
Methane has about 10 the greenhouse effect
of carbon dioxide.
About 580 as much waste water is
produced to make a paper cup compared to
making a polystyrene cup.
The waste chemicals are mainly removed
from the water but there is still at least
10 more chemical waste for paper cups
than for polystyrene ones.
More waste gas is produced for polystyrene
than for paper (per tonne of material made).
Paper cups are heavier than polystyrene
ones, so less waste gas is produced per
polystyrene cup
Polystyrene cups can be recycled. The
recycled material cannot be used for food or
drink containers, but can be made into
packaging, insulation, patio furniture, tiles
and other products.
Only a small proportion of polystyrene
waste is actually recycled at present.
Both paper and polystyrene can be
incinerated and the energy produced can be
used.
Paper provides 20 MJ/kg and polystyrene
produces 40 MJ/kg.
Carbon dioxide is produced in the process.
For the same number of cups, 1 tonne of
landfill waste will be generated if the cups
are made from polystyrene and 6 tonnes if
the cups are made from paper.
252_02-MR_SAC A2 SP.indd 37 17/3/09 08:27:54
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Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
This document may have been altered from the original.
mR3 Paper or plastic? Which is better for the environment?
1
3
5
7
9
2
4
6
8
10
11
13
15
17
12
14
16
The main raw material needed to make
paper is wood, which is a renewable
resource.
However, collecting wood impacts on the
landscape trees have to be cut down both
for use as wood and to make space for
roads so that the wood can be transported.
4.1 g of petroleum is needed to make a paper
cup. 3.2 g of petroleum is needed to make a
polystyrene cup.
A paper cup weighs about 10.1 g.
A polystyrene cup weighs about 1.5 g.
A paper cup costs about 5p;a polystyrene
one costs about 2p.
Paper cups are made from bleached wood
pulp, which is made from wood chips. Only
about half of the chips are turned into pulp.
Bark and some wood waste are burned to
supply energy for the process.
In total, about 33 g of wood and bark are
used per paper cup.
To make a paper cup, chemicals such as
chlorine, sodium hydroxide, bleach,
sulfuric(VI) acid, sulfur and limestone are
needed. These chemicals are not recycled. In
total, about 1.8 g of these chemicals are
needed per cup produced.
More petroleum is needed to make a paper
cup than a polystyrene one. The wood for
paper cups has to be transported by road or
rail to the manufacturing plant.
If the cup has a wax or plastic coating, even
greater amounts of petroleum are needed
per cup.
Efficient catalysts are used to make
polystyrene, so most of the chemicals
involved (other than those from oil) can be
recycled.
Of these additional chemicals all but around
0.05 g per cup are reused in the process.
So much wood pulp is used to make a paper
cup that the whole process requires about:
12 as much steam,
36 as much electricity and
2 as much cooling water
as the process used to make a polystyrene
cup.
A polystyrene cup is made from oil.
Collecting and transporting oil can cause
environmental damage, particularly if spills
occur during drilling or transportation.
The oil (or natural gas) needed to produce
polystyrene cups is taken by pipeline to the
manufacturing plant.
Making polystyrene produces about 20 kg
of waste metal salts per tonne of
polystyrene produced.
Making paper produces about 120 kg of
waste metals per tonne of paper produced
(depending on the type of paper plant).
It is possible to reuse polystyrene cups
because they do not soak up water.
Paper cups could be reused but washing
would destroy them.
Paper cups cannot be recycled. The glues
that hold parts of the cup together cannot
be removed in the recycling process.
Plastic-coated paper is even more difficult
to recycle.
In a landfill site, paper can biodegrade
anaerobically to produce methane and carbon
dioxide in a 2:1 ratio. Paper may biodegrade
very slowly, especially in dry regions of the
world. Polystyrene does not biodegrade.
Methane has about 10 the greenhouse effect
of carbon dioxide.
About 580 as much waste water is
produced to make a paper cup compared to
making a polystyrene cup.
The waste chemicals are mainly removed
from the water but there is still at least
10 more chemical waste for paper cups
than for polystyrene ones.
More waste gas is produced for polystyrene
than for paper (per tonne of material made).
Paper cups are heavier than polystyrene
ones, so less waste gas is produced per
polystyrene cup
Polystyrene cups can be recycled. The
recycled material cannot be used for food or
drink containers, but can be made into
packaging, insulation, patio furniture, tiles
and other products.
Only a small proportion of polystyrene
waste is actually recycled at present.
Both paper and polystyrene can be
incinerated and the energy produced can be
used.
Paper provides 20 MJ/kg and polystyrene
produces 40 MJ/kg.
Carbon dioxide is produced in the process.
For the same number of cups, 1 tonne of
landfill waste will be generated if the cups
are made from polystyrene and 6 tonnes if
the cups are made from paper.
Questions
1 What are the advantages of disposable cups over traditional
cups?
2 What are the main advantages to the environment of using
paper to make disposable cups?
3 What are the main advantages to the environment of using
polystyrene to make disposable cups?
4 Which do you think are better for the environment paper
or polystyrene disposable cups? Explain your answer.
252_02-MR_SAC A2 SP.indd 38 17/3/09 08:27:55
39
Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
This document may have been altered from the original.
What you do
1 Start by chewing a piece of bubble gum until all the taste has gone.
2 Gently pull the gum and then release it.
3 Now pull the gum so that it stretches to about eight times its original length
and then release it.
4 Shape your piece of bubble gum into a fat disc about 2.5 cm across. Wrap it
in some plastic flm and place it in the freezer for about 15 minutes.
5 Take the gum out of the freezer. Observe what happens when you try to
quickly bend the gum. Allow the gum to return to room temperature and
then try to bend it again.
6 Dispose of your gum in a responsible way.
The polymer in bubble gum can be elastic or
glassy, depending on temperature. You can
study both forms with the help of a domestic
freezer.
bubblE gum oR
bubblE glass?
mR4.1
bubblegum
freezer
CARE Do this experiment at home, not at school or college.
CARE Wash your hands before and after handling your own bubble gum. Do not handle other peoples gum.
Requirements
Questions
1 a Does the gum show any elastic properties when it is
gently stretched?
b When the gum is further stretched does it still show
elastic properties and does it completely return to its
original length?
c What term is used to describe this irreversible change?
2 a What happens when you try to bend the gum after it has
been in the freezer?
b Can you explain the result?
c What happens as the gum returns to room temperature?
252_02-MR_SAC A2 SP.indd 39 17/3/09 08:27:55
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Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
This document may have been altered from the original.
What you do
1 Cook some spaghetti, in a saucepan or large beaker, using the manufacturers
instructions for the amount of water and length of time.
2 When cooked, strain the spaghetti so that it is free of water and pour it into a
transparent container.
3 Allow the spaghetti to cool then turn out the solid cake of spaghetti onto a
fat surface (e.g. a plate).
4 Sketch the arrangement of spaghetti strands on the base of the solid cake.
5 The spaghetti acts as a model for the chains in a polymer and the way they
pack together in solid materials.
On your diagram, label the areas where:
a the arrangement resembles a crystalline structure
b the arrangement resembles an amorphous structure.
In this activity, you will use strands of spaghetti
to model how the molecules of some polymers
are aligned in a solid.
usiNg spagHETTi
To modEl polymER
sTRuCTuRE
mR4.2
spaghetti(about250g)
2dm
3
beaker (or saucepan)
Bunsenburner,tripodandgauze(orkitchenhob)
transparentcontainerwithafatbaseandstraightsides(suchasaplasticicecreamorsandwichbox)
plateorotherfatsurface
strainer(sieveorcolander)
CARE Do not eat any spaghetti cooked in the laboratory.
Requirements
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Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
This document may have been altered from the original.
Introduction
The checklist below covers the key points in Chemical Storylines MR1 to
MR5.
The statements listed correspond to learning outcomes in the specifcations
for the A2 examinations. Remember that you will come back to many of these
ideas in later modules.
You will probably have made summary notes of the main ideas that you have
met. Now is a good time to make sure that your notes cover all the points you
need. If you feel that you are not yet able to meet the requirements of all the
statements in the list, you should look again at the areas concerned, seek help
from your teacher if necessary and develop your notes accordingly.
Most of the points are covered in Chemical Ideas, with supporting
information in Chemical Storylines or the activities. However, if the main
source of information is in a storyline or an activity, this is indicated.
What you do
Read and think about each of the statements in the checklist. Put a tick in the
column that best represents your current ability to do what is described.
A I am confdent that I can do this
B I need help to clarify my ideas on this
C I am not yet able to do this
You will be sharing this information with your teacher so that you can work
together to improve your understanding.
at the end of Chemical storylines mR1 to mR5 you should be able to: a b C
explainandpredicttheeffectoftemperature,crystallinityandchainlengthonthepropertiesofpolymers:
temperature:intermolecularbondshavemoreeffectasthetemperatureislowered;apolymersoftensabove
its T
m
and becomes brittle below its T
g
activity mR4.1
crystallinity (regularpackingofthechains,duetotheregularstructureofthepolymer):thechainsarecloser
and the intermolecular bonds have more effect, leading to greater strength activity mR4.2
chain length:withlongerchainstherearemoreintermolecularbonds,leadingtogreaterstrength,and
fexibility depends on the ability of the polymer chains to slide over each other
explainthefollowingwaysthatchemistscanmodifythepropertiesofapolymertomeetparticularneeds:
cold-drawing to make the structure more crystalline
copolymerisation
use of plasticisers
understandthatthepropertiesofallmaterialsdependontheirstructureandbondingandexplainexamples
given relevant information Chemical storylines mR2, mR3, mR4
recognisemembersofthefollowinghomologousseries:aminesandamides
usesystematicnomenclaturetonameandinterpretthenamesofaliphaticprimaryaminesanddiamines
(use the prefx amino- for the NH
2
group together with the parent hydrocarbon, e.g. 2-aminopropane,
1,6-diaminohexane)
explainthedifferencebetweenadditionandcondensationpolymerisation
predictthestructuralformulaofthecondensationpolymerformedfromgivenmonomer(s),andviceversa
describethehydrolysisofestersandamidesbybothaqueousacidsandalkalis,includingsaltformation
where appropriate activity mR2.6
describethefollowingreactionsofamines:
neutralisation by acids
acylation to form an amide
This activity helps you check your knowledge
and understanding of the new topics that you
have covered in this module.
CHECk youR
kNoWlEdgE aNd
uNdERsTaNdiNg
mR5
continued
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Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
This document may have been altered from the original.
recalltheprocedureforpurifyinganorganicsolidproductbyrecrystallisation,andexplainthatthesolvent
used:
must be one in which the substance is very soluble at higher temperatures and insoluble, or nearly so, at
lower temperatures
is saturated by the substance at higher temperatures. On cooling the saturated solution, the substance then
crystallises out to leave the impurities in solution activity mR2.3
explainthebasicnatureoftheaminogroup,intermsofalonepaironthenitrogenacceptingaprotontogive
a cation
understandhowtheprinciplesofgreenchemistryareimportantinthemanufacture,use,recyclingandthe
eventualdisposalofpolymers,including:
minimising any hazardous waste during production of raw materials and their resulting polymers to reduce
any negative impact on the environment
reducing carbon emissions resulting from the life cycle of a polymer
recycling to produce energy and chemical feedstocks
synoptic statements
The following statements describe the knowledge and understanding that you have covered in more detail in
earlier modules, but that you have met or used again when studying The materials Revolution.
Check that you are confdent about these learning outcomes they may be assessed in the A2 examinations in
questions that require you to apply your knowledge and understanding from different areas of the subject.
a b C
explainthetermelectronegativity
recallqualitativelytheelectronegativitytrendsinthePeriodicTable Chemical ideas 3.1
userelativeelectronegativityvaluestopredictbondpolarityinacovalentbond
decidewhetheramoleculeispolarornon-polarfromitsshapeandthepolarityofitsbonds
Chemical ideas 5.3
explain,giveexamplesofandrecogniseingivenexamplesthefollowingtypesofintermolecularbond:
instantaneous dipoleinduced dipole bonds (including dependence on branching and chain length of
organic molecules)
permanent dipolepermanent dipole bonds, hydrogen bonds Chemical ideas 5.3, 5.4
mR5 Check your knowledge and understanding
252_02-MR_SAC A2 SP.indd 42 17/3/09 08:27:55
43
Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
This document may have been altered from the original.
End of module test mR
The Materials Revolution end of module test 60 marks (1 hour)
1 Nylon was invented in 1935 by Wallace Carothers. His invention resulted from a planned research project in which he was trying
to make a polymer in which the molecular chains were built up in a similar way to the protein chains in silk.
He allowed pairs of compounds (e.g. compound a and compound b) to react together under suitable conditions.
H
2
N(CH
2
)
6
NH
2
HOOC(CH
2
)
4
COOH
Compound a Compound b
a i To which homologous series does compound a belong? [1]
ii Give the systematic name for compound a. [1]
iii Show the ions formed when compound a reacts with hydrochloric acid and explain the mechanism by which the amine
group acts as a base. [3]
b i Draw a skeletal formula for the repeating unit in the resulting nylon, showing one unit of a linked to one unit of b. [2]
ii Nylon is a condensation polymer. Explain the meaning of the terms condensation and polymer. [2]
iii Give one difference between the formation of a condensation polymer and that of an addition polymer. [1]
c The same nylon can be made by reacting compound a with compound C, ClOC(CH
2
)
4
COCl.
i Name the functional group in compound C. [1]
ii Apart from the nylon, what other product forms when compound a reacts with compound C? [1]
iii Choose from the following list the term that best describes the reaction of compound a with compound C. [1]
acylation addition esterifcation hydrolysis redox
iv Suggest two reasons why industrial companies do not use compound C to make nylon on a large scale. [2]
d Samples of nylon and high-density poly(ethene) (hdpe) are compared. They have the same average polymer chain lengths.
i Suggest why the chain lengths are kept the same for the comparison. [1]
ii Name the type of intermolecular bond present in hdpe. [1]
iii Name the strongest type of intermolecular bond present in nylon and draw a diagram to show how one of these bonds
forms between two adjacent chains. Show lone pairs and partial charges where appropriate. [5]
iv The nylon has a higher T
g
than the hdpe. Explain the meaning of T
g
and explain why the nylon has a higher T
g
. [4]
[ToTal: 26 maRks]
(OCR Chemistry B (Salters) question, adapted for the 2008 specifcation)
2 Polyesters are widely used as fbres, flms and packaging materials. The repeating unit of the most common polyester, Terylene, is
shown below.
7HU\OHQH
C
O
O O CH
2
CH
2
C
O
a This polyester is hydrolysed using sodium hydroxide. Draw the structures of the organic molecule and the organic ion that are
formed. [2]
b i Name the strongest type of intermolecular bond between the polyester chains. [1]
ii Draw a diagram of two sections of adjacent polyester chains, and show how these intermolecular bonds arise. [2]
c Terylene can be cold-drawn.
i Explain how cold-drawing is carried out. [1]
ii What is meant by crystallinity and what is the effect of cold-drawing on the structure of a polymer? [2]
iii State one property of Terylene that would be affected by cold-drawing. Describe how this property would change and
explain the difference in terms of changes in structure. [3]
d Name two other methods by which a polymers properties can be modifed. [2]
e i Suggest two methods of disposing of objects made from polyesters. [2]
ii Give two reasons why the recycling of plastics is a good idea. [2]
[ToTal: 17 maRks]
(OCR Chemistry B (Salters) question, adapted for the 2008 specifcation)
252_02-MR_SAC A2 SP.indd 43 17/3/09 08:27:55
44
Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
This document may have been altered from the original.
mR End of module test
3 The polymer Kevlar is used to make bullet-proof vests and the cords that reinforce the walls of car tyres. The diagram below
shows the structure of the repeating unit in Kevlar.
.HYODU
OC NH CONH
a i Kevlar is a condensation polymer. Draw the structures of the two monomers from which it is made. [2]
ii What name is given to the CONH group? [1]
b i What reagents and conditions would you use to hydrolyse Kevlar into its monomers in the laboratory? [2]
ii One of the hydrolysis products is a white crystalline solid. Describe how you would obtain a pure sample of this product
by recrystallisation using water as the solvent. [5]
iii Give two important features of the solvent used for recrystallisation. [2]
iv How would you show that the sample you had obtained was pure? [2]
c Kevlar is very useful because it has a high tensile strength, it is fre-resistant and it is low-density. Explain each of these
properties in terms of the structure of Kevlar. [3]
[ToTal: 17 maRks]
(OCR Chemistry B (Salters) question, adapted for the 2008 specifcation)
252_02-MR_SAC A2 SP.indd 44 17/3/09 08:27:55
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Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
This document may have been altered from the original.
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252_12_SAC A2_TT MR.indd 234 17/3/09 08:32:19
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MR
THE MATERIALS REVOLUTION
Concept map
This concept map shows how the major chemical ideas in this teaching module develop throughout the course.
Concept First introduced in
module
Developed in
module(s)
Assumed in
module(s)
Relative atomic mass and relative formula mass EL all
Amount of substance EL DF all
Chemical formulae and inorganic nomenclature EL ES all
Balanced chemical equations EL DF all
Atomic structure EL all
Covalent bonding EL DF, ES, PR all
Relationship between properties, and bonding and
structure
EL MR, TL, AI, CD, O DF, ES, PR, SS
The Periodic Table EL ES, SS, AI several
Catalysis DF A, TL, SS, AI several
Homologous series DF PR several
Nomenclature of organic compounds DF ES, PR, WM, MR,
TL, CD
MD
Structural formulae (full, shortened and skeletal) DF ES, PR all organic
modules
Organic functional groups DF ES, PR, WM, MR,
TL, CD
MD
Properties of alkanes DF several
Alkenes DF PR WM, MR, CD,
MD
Structure of benzene DF CD WM, MR, TL, MD
Alcohols and ethers DF PR, WM, MR ES, CD, MD
Ionic equations ES SS several
Electronegativity and bond polarity ES PR, O several
Intermolecular bonds ES PR, MR, TL, O AI, CD, MD
Reaction mechanisms ES A, PR, MR, TL, CD MD
Industrial applications ES WM, MR, TL, SS,
AI
MD
Bond fssion A PR several
Elimination reactions PR several
Carboxylic acids PR WM, MR TL, AI, CD, MD
Polymers and polymerisation PR MR, TL MD
Esters WM MR AI, CD, MD
Condensation reactions WM MR, TL MD
Acyl (acid) chlorides WM MR CD, MD
Delocalisation of electrons WM CD several
Amines MR TL CD, MD
Amides MR TL CD, MD
Acylation MR CD, MD
Green chemistry MR TL, AI CD, MD
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236
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MR2.1 Naming nylons
This activity provides students with an opportunity to check
their ability to name nylons and to write out structures for
monomers and polymer repeating units. It is designed to
complement Assignment 1 in the Chemical Storylines book
and questions in Chemical Ideas. Through discussion
students are able to identify the aspects that they feel
confdent with and those they are less certain about and may
require help to clarify. Some teachers may wish to laminate
the cards before use.
Nylon 2,4 H
2
N(CH
2
)
2
NH
2

HOOC(CH
2
)
2
COOH
(NH(CH
2
)
2
NHCO(CH
2
)
2
CO)
Nylon 6,6 H
2
N(CH
2
)
6
NH
2

ClOC(CH
2
)
4
COCl
(NH(CH
2
)
6
NHCO(CH
2
)
4
CO)
Nylon 5,10 H
2
N(CH
2
)
5
NH
2

HOOC(CH
2
)
8
COOH
(NH(CH
2
)
5
NHCO(CH
2
)
8
CO)
Nylon 11 H
2
N(CH
2
)
10
COOH
(NH(CH
2
)
10
CO)
MR Advance warning
Activities: notes and answers to questions
Storyline: answers to assignments
1 a i Nylon-6,8
ii Nylon-9,9
iii Nylon-4,4
b i CO(CH
2
)
5
NH, nylon-6
ii NH(CH
2
)
5
NHCO(CH
2
)
5
CO, nylon-5,7
c i H
2
N(CH
2
)
5
NH
2
and ClCO(CH
2
)
8
COCl
ii HCl
iii NH(CH
2
)
5
NHCO(CH
2
)
8
CO
2 a

C
O
O H C O H
O
H O C
H
H
C O
H
H
H
b Permanent dipolepermanent dipole bonds and
instantaneous dipoleinduced dipole bonds.
3 Poly(ethenol) dissolves in aqueous solutions; polyester
made from lactic acid hydrolyses. A more precise rate of
polymer dissolution can be obtained from the latter. Also,
the product of hydrolysis of the lactic acid-based polyester
occurs naturally in the body.
4 a

C NH
O
O
NH
C
b

N
H H
N
C C
O
O O
O
H
H
H
H
c The NH groups in Kevlar become protonated and the
interchain hydrogen bonding is disrupted.
d Protons are transferred from the polymer to the water.
The hydrogen bonding in Kevlar is re-established.
Activity Item(s) Essential/optional Typical quantity per activity
MR2.1 Sets of cards Essential 1 per pair of students
MR2.2 5% decanedioyl dichloride in cyclohexane
5% 1,6-diaminohexane in aqueous solution
5 cm
3
beaker
Essential 1 cm
3
of each liquid,
1 beaker
MR2.3 Nylon-6,6 granules
Heating mantle
Essential
Optional (but
recommended)
2 g
1
MR2.5 Cholesterol
Benzoyl chloride
50 cm
3
conical fask
Essential 1 g cholesterol,
0.4 cm
3
benzoyl chloride
1 fask
MR4.1 Bubble gum, e.g. Hubba Bubba Essential 1 piece
MR4.2 Spaghetti Essential 250 g
Advance warning
The following items needed for activities in this module may not be in your school currently, and might take a little time to
obtain.
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Activities: notes and answers to questions MR
237
Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
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MR2.2 Making nylon
Safety note Information about hazardous chemicals is given on
the activity sheet. Decanedioyl dichloride is corrosive and
toxic and is a powerful irritant to the eyes. It should be
handled in a fume cupboard.
Some students will have already done this activity in earlier
studies. It is not intended that they should repeat the
experiment.
1 Nylon-6,10
2 nH
2
N(CH
2
)
6
NH
2
+ nClOC(CH
2
)
8
COCl
(HN(CH
2
)
6
NHCO(CH
2
)
8
CO)
n
+ 2nHCl
MR2.3 Taking nylon apart
Safety note Information about hazardous chemicals is given on
the activity sheet. The liquid throughout this experiment
contains approximately 5 mol dm
3
sulfuric(VI) acid, which is
very corrosive.
Students should take care when handling the mixture,
particularly when performing the vacuum fltration and adding
the solution to sodium hydrogencarbonate.
Many teachers have preferred to perform Part 1 of this
activity as a demonstration, and to use double quantities and a
250 cm
3
fask. Students can then take samples of impure
crystals and work with them from Part 2 onwards.
The nylon-6,6 granules should have disappeared after
about 1 hour, but the mixture should be refuxed for at least
2
1
/23 hours for hydrolysis to be completed.
If you do not have an electric or gas-heated melting point
apparatus, the setup in Figure 2 in the activity offers a low-cost
alternative. A suitable liquid to use would be medicinal
paraffn or dibutylphthalate. The melting point of pure
hexanedioic acid is 153154 C.
1 It is more soluble in hot water than in cold.
2 The impurities remain dissolved in the solvent as the
hexanedioic acid crystallises.
3 The presence of impurities lowers the melting point. The
substance no longer melts sharply, but over a range.
4 HN(CH
2
)
6
NHCO(CH
2
)
4
CO + H
2
O
H
2
N(CH
2
)
6
NH
2
+ HOOC(CH
2
)
4
COOH
MR2.4 Investigating an amine
Safety note Information about hazardous chemicals is given on
the activity sheet.
As preparation for this activity, it may help to ask students
to think about how ammonia would behave in the four tests.
1 Butylamine is soluble in water.
2 Butylamine forms hydrogen bonds to water molecules.
3 Butylamine solution is alkaline because of the reaction
C
4
H
9
NH
2
+ H
2
O C
4
H
9
NH
3
+
+ OH

4 The smell of the amine is lost on addition of acid because

the free amine is removed by the reaction
C
4
H
9
NH
2
+ H
3
O
+
C
4
H
9
NH
3
+
+ H
2
O
The amine is regenerated on addition of alkali
C
4
H
9
NH
3
+
+ OH

C
4
H
9
NH
2
+ H
2
O
5 Vigorous effervescence. HCl is given off and a colourless
solid is produced.
C
4
H
9
NH
2
+ CH
3
COCl C
4
H
9
NHCOCH
3
+ HCl
6 Sodium hydroxide solution hydrolyses the amide to
produce butylamine.
C
4
H
9
NHCOCH
3
+ OH

C
4
H
9
NH
2
+ CH
3
COO

7 The moistened pH paper turns blue because of the

reaction of butylamine with water (see 3).
MR2.5 Making a liquid crystal
Safety note Information about hazardous chemicals is given on
the activity sheet. The safety precautions described must be
strictly adhered to.
1 As the cholesteryl benzoate is heated gently the solid
moves through a cloudy liquid phase before it goes clear.
This illustrates it passing through a liquid crystal phase.
On cooling, the liquid goes cloudy before solidifying.
2

O
O
MR2.6 Hydrolysing amides and esters
This activity helps students to check that they understand how
the products of hydrolysis of amides and esters depend on the
conditions used to bring this about. By comparing their
answers with those of other students they can identify aspects
that they feel confdent with and those they are less certain
about and may require help to clarify.
Amide or ester Reagent Hydrolysis products
CH
3
CONH
2
HCl CH
3
CONH
3
+
Cl

C
2
H
5
CONH
2
NaOH C
2
H
5
COO

Na
+
+ NH
3
CH
3
COOC
2
H
5
HCl CH
3
COOH + C
2
H
5
OH
HCOOCH
3
NaOH HCOO

Na
+
+ CH
3
OH
( NH(CH
2
)
6
NHOC(CH
2
)
4
CO ) HCl Cl
+
H
3
N(CH
2
)
6
NH
3
+
Cl

+ HOOC(CH
2
)
4
COOH
( NH(CH
2
)
5
NHOC(CH
2
)
8
CO ) NaOH H
2
N(CH
2
)
5
NH
2
+ Na
+

OOC(CH
2
)
8
COO

Na
+
( OCH
2
CH
2
OOCC
6
H
4
CO ) HCl HOCH
2
CH
2
OH + HOOCC
6
H
4
COOH
( O(CH
2
)
3
OOCCO ) NaOH HO(CH
2
)
3
OH + Na
+

OOCCOO

Na
+
( NH(CH
2
)
5
CO ) HCl Cl

+
H
3
N(CH
2
)
5
COOH
( OCH
2
CH
2
CO ) NaOH HOCH
2
CH
2
COO

Na
+
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MR Activities: notes and answers to questions
238
Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
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MR3 Paper or plastic? Which is better for the
environment?
Each group of students will need one set of cards, which could
be cut out and laminated before the lesson.
The aim of this activity is to encourage students to consider
the whole life cycle of an object, including manufacture and
disposal, while assessing the impact on the environment of
making and using that object. Teachers may like to get their
students to discuss which of paper or polystyrene cups they
would opt for (and why) before handing out the information
cards.
A suggested table for summarising the information is given
below.
1 Consumers might want a disposable cup because they
want to take their drink away from the place they have
bought it. Some people prefer disposable cups because
they think that they are more hygienic.
2 Paper cups have the advantages of being biodegradable
(although this has a greater greenhouse gas impact than
burning them) and produce smaller amounts of metal salts
in the manufacturing process.
3 Polystyrene cups use smaller amounts of raw materials and
the manufacturing process produces less waste than the
paper cup manufacturing process. Polystyrene cups are
lighter and so lead to less impact due to transport.
Polystyrene cups can also be re-used and recycled.
Polystyrene cups produce a smaller mass of landfll waste
and could produce more energy if incinerated.
4 This is up to the student, who may choose polystyrene
cups for the reasons described above or may choose
paper perhaps using alternative energy sources for
manufacture and transport in order to reduce the use of
petroleum.
MR4.1 Bubble gum or bubble glass?
1 a The warm gum is elastic.
b If it is pulled too hard it deforms permanently.
2 a The cold gum snaps when it is bent, because it is
below its T
g
.
MR4.2 Using spaghetti to model polymer
structure
Drain the spaghetti well before putting it in the dish. Allow it
to cool before attempting to turn the dish upside down. The
best arrangement is usually seen on the base of the solid cake.
MR5 Check your knowledge and
understanding
This activity ensures that students are aware of the learning
outcomes (specifcation statements) that their assessment will
be based on, and provides an opportunity for them to refect
on how well they understand the ideas that they have covered
in this module. Crucially, it enables teachers to identify areas
where individual students are less confdent, and to provide
appropriate additional support to improve their
understanding.
This activity could be used as part of the preparation for an
end of module test.
Paper cup Polystyrene cup
Mass of wood and bark needed to make one cup 33 g
Mass of petroleum needed to make one cup 4.1 g 3.2 g
Mass of other chemicals needed to make one cup 1.8 g 0.05 g
Mass of one cup 10.1 g 1.5 g
Cost of one cup 5p 2p
Show, by using a tick (3), which cup needs more:
steam
electricity
coolingwater.
3
3
3
Show, by using a tick (3), which cup produces more:
wastewater
waterpollution
metalssalts
wastegases.
3
3
3
3
Can the cup be re-used? Yes Yes
Can the material from the cup be recycled? No Yes
Can the cup be incinerated? Yes Yes
How much energy is produced if 1 kg of cups are incinerated? 20 MJ 40 MJ
What ratio of material would go into landfll from the same number of cups? 6 tonnes 1 tonne
Is the cup biodegradable? Yes No
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MR Answers to end of module tests
Answers to The Materials Revolution end of module test
Q Answer Maximum mark
1 (a) (i) (di)amine 1
1 (a) (ii) 1,6-diaminohexane (1) (ignore commas, dashes and spaces) 1
1 (a) (iii)
+
H
3
N(CH
2
)
6
NH
3
+
(1); Cl

(1); the lone pair on the nitrogen accepts (or forms a covalent bond
with) a proton (1)
3
1 (b) (i)
N
H
O
O
H
N

amide bond shown (1); completely correct (1)
2
1 (b) (ii) Two molecules combine to form a larger molecule with the elimination of a small molecule
(or water) (1);
many molecules joining to form a longer molecule (1)
2
1 (b) (iii) One from: no small molecule (or water) produced (in addition polymerisation); monomers
unsaturated (in addition polymerisation); polymer is just monomers added together or same
empirical formula (addition)
1
1 (c) (i) Acyl chloride 1
1 (c) (ii) Hydrogen chloride/HCl 1
1 (c) (iii) Acylation 1
1 (c) (iv) Two from: it is expensive because it contains chlorine (1); it is dangerous (1); HCl formed is
dangerous/toxic (1)
2
1 (d) (i) Because the number (NOT strength) of intermolecular bonds increases with chain length
(allow alternatives)
1
1 (d) (ii) Instantaneous dipoleinduced dipole 1
1 (d) (iii) Hydrogen bonds (1)

N
H

O
C

correct hydrogen bond shown (1); partial charges on H, N and O (1); lone pair on O pointing
along bond (1); NHO straight (1)
(more of each chain can be shown)
5
1 (d) (iv) The temperature above which the polymer ceases to be brittle (or becomes fexible) or the
reverse argument (1); hydrogen bonds are stronger than instantaneous dipoleinduced dipole
bonds (1); more energy is needed to break the hydrogen bonds (1); (and allow) the chains (or
nylon) to slide over one another (1)
4
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Answers to end of module tests MR
Q Answer Maximum mark
2 (a) HOCH
2
CH
2
OH (1); (allow a more displayed formula)
Na

OOC COO

Na

(1) (Na
+
ions not essential for second mark)
2
2 (b) (i) Permanent dipolepermanent dipole (1); 1
2 (b) (ii)
O
C

O
C

(dotted) line between C of C=O and O on another chain (1); partial charges shown (1) (more
of the chain can be shown)
2
2 (c) (i) The material is stretched 1
2 (c) (ii) A crystalline area is one where the polymer chains (or molecules) are ordered (or parallel) (1);
cold drawing increases the amount of crystallinity (1)
2
2 (c) (iii) Greater tensile strength or less fexible or higher T
g
or T
m
(1);
intermolecular bonds are stronger (not more or greater) (1);
as the chains are closer together (1)
3
2 (d) Copolymerise (1); use plasticiser (1) 2
2 (e) (i) Two from: burning (1); burying (1); recycling (1); depolymerising (1); cracking (1) 2
2 (e) (ii) Two from: conserves resources (1); reduces energy consumption (1); does not use up disposal
facilities (1); reduces gas emissions (1)
2
Q Answer Maximum mark
3 (a) (i)
H
2
N NH
2
HOOC COOH
2
3 (a) (ii) (Secondary) amide 1
3 (b) (i) Concentrated hydrochloric acid (1); refux (1) (if frst mark scored) 2
3 (b) (ii) Five from: use hot water (1); dissolve solid in minimum volume of water (1); flter hot (1);
allow to crystallise (1); flter (1); wash (1); dry (1)
5
3 (b) (iii) Must dissolve substance well at high temperatures (1); (nearly) insoluble at low temperatures
(1) (or words to that effect)
2
3 (b) (iv) Take a melting point (1); check against known melting point or pure if melts sharply (1) 2
3 (c) Tensile strength molecules closely packed or held by hydrogen bonds (1);
fre-resistant few hydrogen atoms or stable rings (1);
low density light atoms, (C, N, O) (1)
3
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