Documenti di Didattica
Documenti di Professioni
Documenti di Cultura
1
Naming nylons
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:
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.
26
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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
17/3/09 08:27:51
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
252_02-MR_SAC A2 SP.indd 27
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MR2.2
Making nylon
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
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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MR2.3
Taking nylon
apart
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
sulfuric(VI) acid
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.
Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
This document may have been altered from the original.
252_02-MR_SAC A2 SP.indd 29
:DWHURXW
&RQGHQVHU
:DWHULQ
1\ORQ
JUDQXOHV
VXOIXULF9,DFLG
+($7
29
17/3/09 08:27:52
7KHUPRPHWHU
*URRYHWRDOORZ
DLULQDQGRXWRI
WKHDSSDUDWXV
0HOWLQJSRLQWWXEH
5XEEHUEDQG
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+($7
30
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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.
Questions
1 What property of hexanedioic acid is made use of in the
recrystallisation process?
2 Explain why recrystallisation should produce a purer
product.
252_02-MR_SAC A2 SP.indd 31
31
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MR2.4
Investigating an
amine
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
CORROSIVE
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.
32
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Investigating an amine
MR2.4
Questions
Test 1: Solubility
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MR2.5
Making a liquid
crystal
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
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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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
252_02-MR_SAC A2 SP.indd 35
35
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MR2.6
Hydrolysing
amides and esters
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
36
252_02-MR_SAC A2 SP.indd 36
Hydrolysis product(s)
17/3/09 08:27:54
MR3
Paper or plastic?
Which is
better for the
environment?
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.
252_02-MR_SAC A2 SP.indd 37
37
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MR3
9
Questions
1 What are the advantages of disposable cups over traditional
cups?
38
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MR4.1
Bubble gum or
bubble glass?
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
2 a
b
c
252_02-MR_SAC A2 SP.indd 39
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?
39
17/3/09 08:27:55
MR4.2
Using spaghetti
to model polymer
structure
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.
40
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MR5
Check your
knowledge and
understanding
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
Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
This document may have been altered from the original.
252_02-MR_SAC A2 SP.indd 41
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MR5
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
42
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MR
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
[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.
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]
[2]
252_02-MR_SAC A2 SP.indd 43
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MR
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)
44
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234
17/3/09 08:32:19
MR5 SUMMARY
5.7
CHEMICAL IDEAS
CHEMICAL STORYLINE
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.
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)
EL
all
Amount of substance
EL
DF
all
EL
ES
all
EL
DF
all
Atomic structure
EL
all
Covalent bonding
EL
DF, ES, PR
all
EL
EL
ES, SS, AI
several
Catalysis
DF
A, TL, SS, AI
several
Homologous series
DF
PR
several
DF
MD
DF
ES, PR
all organic
modules
DF
MD
Properties of alkanes
DF
several
Alkenes
DF
PR
Structure of benzene
DF
CD
DF
PR, WM, MR
ES, CD, MD
Ionic equations
ES
SS
several
ES
PR, O
several
Intermolecular bonds
ES
AI, CD, MD
Reaction mechanisms
ES
MD
Industrial applications
ES
MD
Bond fission
PR
several
Elimination reactions
PR
several
Carboxylic acids
PR
WM, MR
PR
MR, TL
MD
WM
MR
AI, CD, MD
Esters
Condensation reactions
WM
MR, TL
MD
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
235
17/3/09 08:32:19
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
MR2.1
Sets of cards
Essential
MR2.2
Essential
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
Essential
1 piece
MR4.2
Spaghetti
Essential
250g
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.
236
252_12_SAC A2_TT MR.indd 236
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
17/3/09 08:32:20
O
O
Amide or ester
Reagent
Hydrolysis products
CH3CONH2
HCl
CH3CONH3+ Cl
C2H5CONH2
NaOH
CH3COOC2H5
HCl
CH3COOH + C2H5OH
HCOOCH3
NaOH
NH(CH
(
)
2)6NHOC(CH2)4CO
HCl
Cl +H3N(CH2)6NH3+ Cl + HOOC(CH2)4COOH
NH(CH
(
)
2)5NHOC(CH2)8CO
NaOH
OCH
(
)
2CH2OOCC6H4CO
HCl
HOCH2CH2OH + HOOCC6H4COOH
O(CH
(
)
2)3OOCCO
NaOH
NH(CH
(
)
2)5CO
HCl
Cl +H3N(CH2)5COOH
OCH
(
)
2CH2CO
NaOH
HOCH2CH2COO Na+
MR
237
17/3/09 08:32:20
MR
Polystyrene cup
33g
4.1g
3.2g
1.8g
0.05g
10.1g
1.5g
5p
2p
3
3
3
3
3
3
3
Yes
Yes
No
Yes
Yes
Yes
20MJ
40MJ
What ratio of material would go into landfill from the same number of cups?
6 tonnes
1 tonne
Yes
No
238
252_12_SAC A2_TT MR.indd 238
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MR
Answer
Maximum mark
1 (a) (i)
(di)amine
1 (a) (ii)
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);
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)
1 (d) (iii)
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)
304
252_20_SAC A2_EMT Answers.indd 304
17/3/09 08:34:19
Answer
Maximum mark
2 (a)
NaOOC
MR
COONa
(1) (Na+ ions not essential for second mark)
2 (b) (i)
2 (b) (ii)
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)
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 (c) (iii)
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)
305
17/3/09 08:34:19