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MR2.

1
Naming nylons

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.

Requirements
set of cards showing names of nylons, structures of monomers and structures of polymer repeating units

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.

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H2N(CH2)2NH2

H2N(CH2)6NH2

H2N(CH2)5NH2

H2N(CH2)10COOH

(NH(CH2)2NH

HOOC(CH2)2COOH

ClOC(CH2)4COCl

(NH(CH2)5NH

HOOC(C

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Nylo

Naming nylons

HOOC(CH2)8COOH

(NH(CH2)6NHCO(CH2)4CO)

COOH

(NH(CH2)2NHCO(CH2)2CO)

(NH(CH2)10CO)

)4COCl

(NH(CH2)5NHCO(CH2)8CO)

Nylon-6,6

Nylon-2,4

Nylon-11

)6NH2

MR2.1

Nylon-5,10

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MR2.2
Making nylon

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.

Requirements
access to a fume cupboard
5cm3 beaker
glass rod or test tube
tweezers
protective gloves
decanedioyl dichloride, 35% solution in cyclohexane (1cm3)
1,6-diaminohexane solution, 35% aqueous solution (1cm3)
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.

decanedioyl chloride in
cyclohexane solution
HIGHLY
FLAMMABLE

HARMFUL

WEAR EYE
PROTECTION

WEAR GLOVES

CARE Eye protection


(goggles) and gloves must
be worn.

What you do
1 Pour about 1cm3 of the 1,6-diaminohexane solution into a 5cm3 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 film 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.

Questions
1 What is the name of the nylon you have made?

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2 Write out an equation to show the formation of this nylon.

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MR2.3
Taking nylon
apart

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.

Requirements
electric heating mantle
melting-point apparatus for use up to 150C
thin-walled capillary tubes (or melting-point tubes)
apparatus for vacuum (suction) filtration
100cm3 boiling flask (e.g. round-bottomed flask)
Liebig condenser
250cm3 conical flasks (2)
100cm3 measuring cylinder
10cm3 measuring cylinder
250cm3 beakers (2)
watch glass
anti-bumping granules (boiling chips)
nylon-6,6 granules (2g)
sulfuric(VI) acid, approximately 5moldm3 (35cm3)
saturated sodium hydrogencarbonate solution (20cm3)
sodium hydroxide solution, 2moldm3 (5cm3)
ice
universal indicator paper

sodium hydroxide solution


CORROSIVE

sulfuric(VI) acid
CORROSIVE

CARE Eye protection (goggles)


must be worn throughout.
WEAR EYE
PROTECTION

CARE Sulfuric acid of this concentration is very corrosive.

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
find 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 5.5moldm3) for the
hydrolysis.

What you do
Part 1: Breaking down the nylon
1 Place 2g of nylon-6,6 granules into a 100cm3 flask to which a reflux
condenser can be attached.
2 Pour 35cm3 of 5moldm3 sulfuric(VI) acid into the flask. (CARE Sulfuric acid of
this concentration is very corrosive.) Fit the condenser to the flask (Figure 1).
3 Place the reaction flask and condenser in the heating mantle. Heat the
reaction mixture under reflux 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 flask 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 filtration. Keep the
filtrate for use later.
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:DWHURXW

&RQGHQVHU

:DWHULQ

1\ORQ
JUDQXOHV
VXOIXULF 9, DFLG

+($7

Figure 1 Breaking down the nylon.

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MR2.3 Taking nylon apart


Part 2: Purifying the hexanedioic acid by recrystallisation
Your solid now needs to be purified by recrystallisation.
6 Place your hexanedioic acid crystals in a 250cm3 conical flask. Add 10cm3 of
distilled water. Hold the neck of the flask with an insulating holder and
gently heat the flask, swirling the contents at the same time. If some crystals
remain when the water starts to boil, add a further 5cm3 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 flask 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 flask, 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 filtration 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 153C. Find the melting point of your crystals and
compare it with this value.
This is what you do to determine a melting point.
10 Carefully heat one end of a small thin-walled capillary tube a melting-point
tube so that the opening is just sealed. Leave the tube to cool.
11 Grind a small quantity of your dry crystals in one corner of the watch glass
until you have a fine powder. Tap the open end of the melting-point tube
into the fine 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 Repeat the procedure until you have about 0.51cm depth of powder in the
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
shown below if you are using one of these, steps 13 and 14 describe how
to use it.

7KHUPRPHWHU
*URRYHWRDOORZ
DLULQDQGRXWRI
WKHDSSDUDWXV
0HOWLQJSRLQWWXEH
5XEEHUEDQG

6XLWDEOHOLTXLG

+($7

Figure 2 Melting-point apparatus.

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
flame. 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.

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Taking nylon apart

MR2.3

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
to cool down to about 10C below the value you have just recorded. 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 filtrate obtained in Part 1, because it has
formed a soluble salt by reacting with the sulfuric(VI) acid.
17 Take 5cm3 of the filtrate and carefully pour it into 20cm3 of saturated sodium
hydrogencarbonate solution in a 250cm3 beaker. (CARE Do not add the
filtrate all in one go or the mixture will fizz 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 5cm3 of 2moldm3 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 flesh.)

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.

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MR2.4
Investigating an
amine

In this activity you will investigate the


properties of the amine, butylamine.

Requirements
access to a fume cupboard
test tubes and rack
butylamine (2cm3)
concentrated hydrochloric acid (a few drops)
sodium hydroxide solution, 2moldm3 (10cm3)
ethanoyl chloride (2cm3)
universal indicator paper

butylamine
HIGHLY
FLAMMABLE

CORROSIVE

HIGHLY
FLAMMABLE

CORROSIVE

ethanoyl chloride

CARE Butylamine and ethanoyl chloride are volatile and


have unpleasant, highly flammable vapours. Use the
bottles in a fume cupboard and avoid inhaling the vapours.
concentrated hydrochloric acid

CORROSIVE

sodium hydroxide solution


CORROSIVE

CARE Eye protection


must be worn.
WEAR EYE
PROTECTION

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 1cm 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 2cm depth of 2moldm3 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 1cm depth
of water and carefully stir the mixture.
b Now add 3cm depth of 2moldm3 sodium hydroxide solution.
c Warm the mixture, and hold a piece of moistened pH paper at the mouth of
the test tube.

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Investigating an amine

MR2.4

Questions
Test 1: Solubility

Test 3: Adding ethanoyl chloride

1 Is butylamine soluble in water?

5 Write an equation for any reaction that occurs resulting in


the formation of a secondary amide.

2 How can you explain any solubility in terms of bonding


between particles?

Test 4: Hydrolysing an amide

3 Write an equation to explain any change to the pH of the


water.

6 Write an equation for the reaction between the secondary


amide and sodium hydroxide.

Test 2: Adding acid and alkali

7 Explain any change to the pH paper in terms of the process


occurring in the test tube.

4 Write equation(s) for any changes you have noted.

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MR2.5
Making a liquid
crystal

In this activity you will make and test a


compound that shows liquid crystal properties.

Requirements
access to a fume cupboard
250cm3 beaker
50cm3 conical flask
apparatus for setting up a steam bath
apparatus for vacuum filtration using a Hirsch funnel
boiling tube
stirring rod
watch glass
microscope slide
tongs
cholesterol (1g)
pyridine (3cm3)
benzoyl chloride (0.4cm3)
ethyl ethanoate (15cm3)
methanol (15cm3)
crushed ice
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.

pyridine
HIGHLY
FLAMMABLE

HARMFUL

benzoyl chloride
CORROSIVE

methanol
HIGHLY
FLAMMABLE

TOXIC

HIGHLY
FLAMMABLE

IRRITANT

ethyl ethanoate

CARE Eye protection and


protective gloves must be
worn.

CARE Pyridine, methanol and ethyl ethanoate are all highly


flammable. Avoid naked flames.

WEAR EYE
PROTECTION

WEAR GLOVES

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 1g of cholesterol in 3cm3 of pyridine
in a 50cm3 conical flask.
2 Add 0.4cm3 of benzoyl chloride to the flask. (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 flask to cool.
4 Add 15cm3 of methanol to the mixture in the flask.
5 Collect the solid cholesteryl benzoate by suction filtration using a Hirsch
funnel. Use a little methanol to rinse the flask and wash the crystals.
6 To obtain high-quality crystals, recrystallise your crude product using about
15cm3 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 0.1g) on the end of a microscope slide. Hold the slide with
tongs above a small Bunsen burner flame. Observe what happens when the
compound is gently heated. Let the compound cool down and again note
changes in the appearance of your sample.

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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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MR2.6
Hydrolysing
amides and esters

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.

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 confident about working out, to help
you when you come to revise this topic at a later date.
Table 1
Amide or ester

Reagent

CH3CONH2

HCl

C2H5CONH2

NaOH

CH3COOC2H5

HCl

HCOOCH3

NaOH

( NH(CH2)6NHOC(CH2)4CO
)

HCl

( NH(CH2)5NHOC(CH2)8CO
)

NaOH

( OCH2CH2OOCC6H4CO
)

HCl

( O(CH2)3OOCCO
)

NaOH

( NH(CH2)5CO
)

HCl

( OCH2CH2CO
)

NaOH

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Hydrolysis product(s)

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MR3
Paper or plastic?
Which is
better for the
environment?

This activity gives you an opportunity to


compare the impact on the environment of the
manufacture and disposal of paper and plastic
disposable cups.

Requirements
set of information cards

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 find it useful to design a table in which to summarise the
information about paper and polystyrene cups.

1 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.

2 A polystyrene cup is made from oil.


Collecting and transporting oil can cause
environmental damage, particularly if spills
occur during drilling or transportation.

3 4.1 g of petroleum is needed to make a paper


cup. 3.2 g of petroleum is needed to make a
polystyrene cup.

4 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.

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.
5 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.

7 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.

The oil (or natural gas) needed to produce


polystyrene cups is taken by pipeline to the
manufacturing plant.

If the cup has a wax or plastic coating, even


greater amounts of petroleum are needed
per cup.

6 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.

8 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.

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MR3
9

Paper or plastic? Which is better for the environment?


About 580 as much waste water is
produced to make a paper cup compared to
making a polystyrene cup.

10 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).

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.
11 More waste gas is produced for polystyrene
than for paper (per tonne of material made).

12 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 are heavier than polystyrene


ones, so less waste gas is produced per
polystyrene cup

13 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.

15 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.

14 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.

16 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.

17 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?

3 What are the main advantages to the environment of using


polystyrene to make disposable cups?

2 What are the main advantages to the environment of using


paper to make disposable cups?

4 Which do you think are better for the environment paper


or polystyrene disposable cups? Explain your answer.

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MR4.1
Bubble gum or
bubble glass?

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.

Requirements
bubble gum
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.

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 flat disc about 2.5cm across. Wrap it
in some plastic film 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.

Questions
1 a

Does the gum show any elastic properties when it is


gently stretched?
When the gum is further stretched does it still show
elastic properties and does it completely return to its
original length?
What term is used to describe this irreversible change?

2 a

b
c

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What happens when you try to bend the gum after it has
been in the freezer?
Can you explain the result?
What happens as the gum returns to room temperature?

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MR4.2
Using spaghetti
to model polymer
structure

In this activity, you will use strands of spaghetti


to model how the molecules of some polymers
are aligned in a solid.

Requirements
spaghetti (about 250g)
2dm3 beaker (or saucepan)
Bunsen burner, tripod and gauze (or kitchen hob)
transparent container with a flat base and straight sides (such as a plastic ice cream or sandwich box)
plate or other flat surface
strainer (sieve or colander)
CARE Do not eat any spaghetti cooked in the laboratory.

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
flat 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.

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MR5
Check your
knowledge and
understanding

This activity helps you check your knowledge


and understanding of the new topics that you
have covered in this module.

Introduction
The checklist below covers the key points in Chemical Storylines MR1 to
MR5.
The statements listed correspond to learning outcomes in the specifications
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 confident 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:

explain and predict the effect of temperature, crystallinity and chain length on the properties of polymers:
temperature: intermolecular bonds have more effect as the temperature is lowered; a polymer softens above
its Tm and becomes brittle below its Tg
Activity MR4.1
crystallinity (regular packing of the chains, due to the regular structure of the polymer): the chains are closer
and the intermolecular bonds have more effect, leading to greater strength
Activity MR4.2
chain length: with longer chains there are more intermolecular bonds, leading to greater strength, and
flexibility depends on the ability of the polymer chains to slide over each other
explain the following ways that chemists can modify the properties of a polymer to meet particular needs:
cold-drawing to make the structure more crystalline
copolymerisation
use of plasticisers
understand that the properties of all materials depend on their structure and bonding and explain examples
given relevant information
Chemical Storylines MR2, MR3, MR4
recognise members of the following homologous series: amines and amides
use systematic nomenclature to name and interpret the names of aliphatic primary amines and diamines
(use the prefix amino- for the NH2 group together with the parent hydrocarbon, e.g. 2-aminopropane,
1,6-diaminohexane)
explain the difference between addition and condensation polymerisation
predict the structural formula of the condensation polymer formed from given monomer(s), and vice versa
describe the hydrolysis of esters and amides by both aqueous acids and alkalis, including salt formation
where appropriate
Activity MR2.6
describe the following reactions of amines:
neutralisation by acids
acylation to form an amide
continued
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MR5

Check your knowledge and understanding

recall the procedure for purifying an organic solid product by recrystallisation, and explain that the solvent
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
explain the basic nature of the amino group, in terms of a lone pair on the nitrogen accepting a proton to give
a cation
understand how the principles of green chemistry are important in the manufacture, use, recycling and the
eventual disposal of polymers, 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 confident 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.
explain the term electronegativity
recall qualitatively the electronegativity trends in the Periodic Table

Chemical Ideas 3.1

use relative electronegativity values to predict bond polarity in a covalent bond


decide whether a molecule is polar or non-polar from its shape and the polarity of its bonds

Chemical Ideas 5.3
explain, give examples of and recognise in given examples the following types of intermolecular bond:
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

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MR

End of module test

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.

H2N(CH2)6NH2

HOOC(CH2)4COOH

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.
ii Nylon is a condensation polymer. Explain the meaning of the terms condensation and polymer.
iii Give one difference between the formation of a condensation polymer and that of an addition polymer.

[2]
[2]
[1]

[1]
[1]
[1]

The same nylon can be made by reacting compound A with compound C, ClOC(CH2)4COCl.
i Name the functional group in compound C. 
ii Apart from the nylon, what other product forms when compound A reacts with compound C?
iii Choose from the following list the term that best describes the reaction of compound A with compound C.

acylation addition esterification hydrolysis redox

iv Suggest two reasons why industrial companies do not use compound C to make nylon on a large scale.

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]
[4]
iv The nylon has a higher Tg than the hdpe. Explain the meaning of Tg and explain why the nylon has a higher Tg.
[TOTAL: 26 MARKS]
(OCR Chemistry B (Salters) question, adapted for the 2008 specification)





[2]

2 Polyesters are widely used as fibres, films and packaging materials. The repeating unit of the most common polyester, Terylene, is
shown below.

CH2

CH2

7HU\OHQH
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.
ii Draw a diagram of two sections of adjacent polyester chains, and show how these intermolecular bonds arise.
c


[1]
[2]

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 modified.

[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 specification)

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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.

OC

CONH

NH

.HYODU
a i Kevlar is a condensation polymer. Draw the structures of the two monomers from which it is made.
ii What name is given to the CONH group?

[2]
[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 fire-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 specification)

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MR5 SUMMARY

MR5 Check your knowledge and understanding

Polymer properties by design

MR4 MATERIALS WITH UNUSUAL PROPERTIES

MR4.1 Bubble gum or bubble glass? (P)


MR4.2 Using spaghetti to model polymer structure (P)

5.7

15.10 Green chemistry and recycling

MR3 RE-USE OR REFUSE?

MR2.5 Making a liquid crystal (P)

MR3 Paper or plastic? Which is better for the environment?

13.3 Carboxylic acids and their derivatives


13.4 The OH group in alcohols, phenols and acids

CHEMICAL IDEAS

MR2.6 Hydrolysing amides and esters (P)

MR2 MAKING AND BREAKING POLYMERS

MR1 DESIGNING MATERIALS

CHEMICAL STORYLINE

13.8 Amines and amides


5.3 Bonds between molecules: temporary and permanent
dipoles
5.4 Bonds between molecules: hydrogen bonding
3.1 Chemical bonding (section on electronegativity and
bond polarity)
13.5 Esters

MR2.1 Naming nylons


MR2.2 Making nylon (P)
MR2.3 Taking nylon apart (P)
MR2.4 Investigating an amine (P)

ACTIVITIES

This shows the relationship between the Chemical Storylines, the Activities and the Chemical Ideas. To aid planning, laboratory-based practical work is indicated by (P), activities involving IT
skills are indicated by (IT) and those developing study skills by (S).
Chemical Ideas references in italics are covered in earlier modules and are included in synoptic learning outcomes for this module in the specifications. Emphasis in teaching and learning
should be on the new (non-italicised) sections of Chemical Ideas. The degree to which revisited Chemical Ideas are studied will depend on the needs of individual students.

Map of the module: The Materials Revolution

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 fission

PR

several

Elimination reactions

PR

several

Carboxylic acids

PR

WM, MR

TL, AI, CD, MD

Polymers and polymerisation

PR

MR, TL

MD

WM

MR

AI, CD, MD

Esters
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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MR

Advance warning

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.
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
5cm3 beaker

Essential

1cm3 of each liquid,


1 beaker

MR2.3

Nylon-6,6 granules
Heating mantle

Essential
Optional (but
recommended)

2g
1

MR2.5

Cholesterol
Benzoyl chloride
50cm3 conical flask

Essential

1g cholesterol,
0.4cm3 benzoyl chloride
1 flask

MR4.1

Bubble gum, e.g. Hubba Bubba

Essential

1 piece

MR4.2

Spaghetti

Essential

250g

Storyline: answers to assignments


1 a


b

c


2 a

i Nylon-6,8
ii Nylon-9,9
iii Nylon-4,4
i CO(CH2)5NH, nylon-6
ii NH(CH2)5NHCO(CH2)5CO, nylon-5,7
i H2N(CH2)5NH2 and ClCO(CH2)8COCl
ii HCl
iii NH(CH2)5NHCO(CH2)8CO
H

4 a

NH

O
C

NH
C
O


b
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.

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.

Activities: notes and answers to questions


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
confident with and those they are less certain about and may
require help to clarify. Some teachers may wish to laminate
the cards before use.

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H2N(CH2)2NH2
HOOC(CH2)2COOH


(NH(CH2)2NHCO(CH2)2CO)
Nylon 6,6 H2N(CH2)6NH2
ClOC(CH2)4COCl


(NH(CH2)6NHCO(CH2)4CO)
Nylon 5,10 H2N(CH2)5NH2
HOOC(CH2)8COOH


(NH(CH2)5NHCO(CH2)8CO)
Nylon 11 H2N(CH2)10COOH

(NH(CH2)10CO)
Nylon 2,4

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Activities: notes and answers to questions

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 nH2N(CH2)6NH2 + nClOC(CH2)8COCl
(HN(CH2)6NHCO(CH2)8CO)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 5moldm3 sulfuric(VI) acid, which is
very corrosive.
Students should take care when handling the mixture,
particularly when performing the vacuum filtration 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
250cm3 flask. 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 refluxed for at least
21/23 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
paraffin or dibutylphthalate. The melting point of pure
hexanedioic acid is 153154C.
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(CH2)6NHCO(CH2)4CO + H2O
H2N(CH2)6NH2 + HOOC(CH2)4COOH

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
C4H9NH2 + H2O C4H9NH3+ + OH
4 The smell of the amine is lost on addition of acid because
the free amine is removed by the reaction
C4H9NH2 + H3O+ C4H9NH3+ + H2O
The amine is regenerated on addition of alkali
C4H9NH3+ + OH C4H9NH2 + H2O
5 Vigorous effervescence. HCl is given off and a colourless
solid is produced.
C4H9NH2 + CH3COCl C4H9NHCOCH3 + HCl
6 Sodium hydroxide solution hydrolyses the amide to
produce butylamine.
C4H9NHCOCH3 + OH C4H9NH2 + CH3COO
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 confident with and those they are less certain
about and may require help to clarify.

Amide or ester

Reagent

Hydrolysis products

CH3CONH2

HCl

CH3CONH3+ Cl

C2H5CONH2

NaOH

C2H5COO Na+ + NH3

CH3COOC2H5

HCl

CH3COOH + C2H5OH

HCOOCH3

NaOH

HCOO Na+ + CH3OH

NH(CH
(
)
2)6NHOC(CH2)4CO

HCl

Cl +H3N(CH2)6NH3+ Cl + HOOC(CH2)4COOH

NH(CH
(
)
2)5NHOC(CH2)8CO

NaOH

H2N(CH2)5NH2 + Na+ OOC(CH2)8COO Na+

OCH
(
)
2CH2OOCC6H4CO

HCl

HOCH2CH2OH + HOOCC6H4COOH

O(CH
(
)
2)3OOCCO

NaOH

HO(CH2)3OH + Na+ OOCCOONa+

NH(CH
(
)
2)5CO

HCl

Cl +H3N(CH2)5COOH

OCH
(
)
2CH2CO

NaOH

HOCH2CH2COO Na+

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Activities: notes and answers to questions

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 landfill 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 Tg.

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 (specification statements) that their assessment will
be based on, and provides an opportunity for them to reflect
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 confident, 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

33g

Mass of petroleum needed to make one cup

4.1g

3.2g

Mass of other chemicals needed to make one cup

1.8g

0.05g

Mass of one cup

10.1g

1.5g

Cost of one cup

5p

2p

Show, by using a tick (3), which cup needs more:


steam
electricity
cooling water.

3
3
3

Show, by using a tick (3), which cup produces more:


waste water
water pollution
metals salts
waste gases.

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 1kg of cups are incinerated?

20MJ

40MJ

What ratio of material would go into landfill from the same number of cups?

6 tonnes

1 tonne

Is the cup biodegradable?

Yes

No

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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 (a) (ii)

1,6-diaminohexane (1) (ignore commas, dashes and spaces)

1 (a) (iii)

+
H3N(CH2)6NH3+ (1); Cl (1); the lone pair on the nitrogen accepts (or forms a covalent bond
with) a proton (1)

1 (b) (i)

O
H
N
N
H
O
amide bond shown (1); completely correct (1)

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)


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 (c) (i)

Acyl chloride

1 (c) (ii)

Hydrogen chloride/HCl

1 (c) (iii)

Acylation

1 (c) (iv)

Two from: it is expensive because it contains chlorine (1); it is dangerous (1); HCl formed is
dangerous/toxic (1)

1 (d) (i)

Because the number (NOT strength) of intermolecular bonds increases with chain length
(allow alternatives)

1 (d) (ii)

Instantaneous dipoleinduced dipole

1 (d) (iii)

Hydrogen bonds (1)

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)
1 (d) (iv)

The temperature above which the polymer ceases to be brittle (or becomes flexible) 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)

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Answers to end of module tests


Q

Answer

Maximum mark

2 (a)

HOCH2CH2OH (1); (allow a more displayed formula)

NaOOC

MR

COONa
(1) (Na+ ions not essential for second mark)

2 (b) (i)
2 (b) (ii)

Permanent dipolepermanent dipole (1);

1
2

C
O

O
(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 (c) (i)

The material is stretched

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)

Greater tensile strength or less flexible or higher Tg or Tm (1);

2 (c) (iii)

intermolecular bonds are stronger (not more or greater) (1);


as the chains are closer together (1)
2 (d)

Copolymerise (1); use plasticiser (1)

2 (e) (i)

Two from: burning (1); burying (1); recycling (1); depolymerising (1); cracking (1)

2 (e) (ii)

Two from: conserves resources (1); reduces energy consumption (1); does not use up disposal
facilities (1); reduces gas emissions (1)

Answer

Maximum mark

3 (a) (i)

HOOC

COOH

H2N

NH2

3 (a) (ii)

(Secondary) amide

3 (b) (i)

Concentrated hydrochloric acid (1); reflux (1) (if first mark scored)

3 (b) (ii)

Five from: use hot water (1); dissolve solid in minimum volume of water (1); filter hot (1);
allow to crystallise (1); filter (1); wash (1); dry (1)

3 (b) (iii)

Must dissolve substance well at high temperatures (1); (nearly) insoluble at low temperatures
(1) (or words to that effect)

3 (b) (iv)

Take a melting point (1); check against known melting point or pure if melts sharply (1)

3 (c)

Tensile strength molecules closely packed or held by hydrogen bonds (1);

fire-resistant few hydrogen atoms or stable rings (1);


low density light atoms, (C, N, O) (1)

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


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