20 Polymerisation MS Unlocked

Answer Mark
Question
1(e)(i) lone pair 1 1

receive / accepts a proton / H+ 1
2
1(e)(ii) H2NCH2CH2NH2 + 2HCl

Polymerisation WS 1
ClH3NCH2CH2NH3Cl
OR H2NCH2CH2NH2 + 2H+ H3N+CH2CH2N+H3 1

1
1 1(f)(i) amide bond, displayed or –CONH– 1
rest of the molecule with continuation bonds 1
O O
H H
N N
N N
H H
O O 2
1(f)(ii) condensation / addition – elimination 1

1
1(f)(iii) any named polyalkene / eg polyethene, PVC 1
allow Bakelite or Kevlar

1
20
Total:
[W'16 P41 Q1]
© UCLES 2016
Bilal Hameed Polymerisation 1

Page 10 Mark Scheme Syllabus Paper
Cambridge International AS/A Level – March 2016 9701 42
2
Question Answer Mark
2 9 (a) (i) polyester : Terylene / polylactic acid (PLA) / 1
polyamide : nylon / Kevlar / Nomex
(ii) water or hydrochloric acid / hydrogen chloride 1
(b) (i) 2
polymer biodegradable
A yes
B yes
C no
D yes
(ii) 2
or equivalent 1,4-diacyl chloride

HOCH2CH2OH and
or equivalent 1,4-diester
(c) (i) V: 1
it has two amine / NH2 groups (which can be protonated) or
it has an amine / NH2 group on its side chain / R group
(ii) four (TT, TU, UT, UU) 1
(iii) hydrogen bonds; 2

between the O / N atoms or named group (in the polypeptide) and water;
or
ion-dipole attractions;
between NH3+ / CO2– and water;
[M’16 P42 Q9]
© Cambridge International Examinations 2016
Polymerisation 1 Bilal Hameed

9701/42 Cambridge International AS/A Level – Mark Scheme March 2017
3
PUBLISHED
Question Answer Marks
3 7(a) 1
RO
O
NH O
HO NH CH3
O O
OH
7(b)(i) H+(aq) + heat 1
7(b)(ii) hydrolysis 1
7(b)(iii) CH3OH 1
7(c)(i) white precipitate 1
7(c)(ii) C14H19O6N + 3NaOH C14H16O6NNa3 + 3H2O 2
7(d)(i) no change / colour remains orange 1
7(d)(ii) 2
R H O
N
N
H O R
amide bond displayed 1
two repeat units 1
7(e)(i) seven 1
[M’17 P42 Q7]
© UCLES 2017 Page 10 of 12

9701/41 Cambridge International AS/A Level – Mark Scheme October/November
4
PUBLISHED 2017
4 5(a) nitrile; alkene; chloro; benzene / arene 2
5(b) 1
addition (polymerisation) 1
[W'17 P41 Q5]

3(c)(i) (spectrum of M) contains a broad peak (for O–H) at 2500–3000 cm–1 1
or (spectrum of M) contains peak (for C=O) at 1640–1750 cm–1
or (spectrum of M) lacks (NH2 peak) at 3300–3500 cm–1
3(c)(ii) 5 or 6 peaks 1
5
OH/NH protons exchange with deuterium or –OH / –NH + D2O –OD / –ND + DHO 1
5 3(d) ester and hydrolysed 1
[W'17 P42 Q3]

4(a)(i) Eocell = 1.00 – (–0.26) = (+)1.26 V 1
4(a)(ii) VO2+ + V2+ + 2H+ VO2+ + V3+ + H2O 1
4(a)(iii) 4
solutions labelled correctly in one half-cell [1]

solutions labelled correctly in both half-cells [1]
two graphite or platinum electrodes [1]
salt bridge and voltmeter [1]

• substrate shape is complementary to active site
• the substrate binds / bonds / fits into the active site
• products are released
• lower EA / bonds weakened in substrate
6
6 7(a)(i) CaC2 + 2H2O C2H2 + Ca(OH)2 1
7(a)(ii) 1
7(b) CnH2n–2 1
7(c)(i) delocalised electrons 1
7(c)(ii) CH 1
9701/42 Cambridge International AS/A Level – Mark Scheme October/November
7(c)(iii) less dense PUBLISHED 2017
1
7(d)(i) 3
2 curly arrows [1]

dipole [1]
intermediate [1]
7(d)(ii) nucleophilic addition 1
7(d)(iii) 2
Q R
7(e) CH3CHO HCO2H CH3COCH3 HO2CCO2H 4
hot acidified
MnO4– (aq)
alkaline I2(aq)
Tollens’ reagent
[W'17 P42 Q7]

7
PUBLISHED
7 7(a)(i) CH3 3
[1]
O + H2O
O
O O [1] [1]
7(a)(ii) • for addition polymerisation: 2

S will be negative, as many gas molecules are combining to form one (large) molecule
• for condensation polymerisation:
S likely to be positive, (as each pair of monomer molecules join to chain, two molecules of) water forms
7(b)(i) (RCO2H + H2NR' ) RCONHR' + H2O 1
7(b)(ii) broken: C-O, N-H 2

formed: C-N, O-H
7(b)(iii) bonds formed: 305 + 460 or 765 2

bonds broken: 360 + 390 or 750 (both)
H = 750 – 765 = –15 (kJ)
7(c) (If G = 0, then) H = T S 2

S = H / T = –6000 / 298 = –20.1 (J mol–1 K–1)
7(d)(i) heat with (conc.) KMnO4 1

9701/42
7(d)(ii) Sn and HCl Cambridge International AS/A Level – Mark Scheme March 20182
heat + conc. (then add NaOH) PUBLISHED
7(e) intermolecular force group(s) involved 2

hydrogen bonding N-H and C=O (of amide)
induced dipole / van der Waals benzene rings
Question Answer [M’18 P42Marks

Q7]
8(a)(i) 7 peaks 1
8(a)(ii) C=O 1670–1740 2
OH 3200–3600
Or C-O 1000–1260
8(b)(i) step 1 heat with Al Cl3 + (CH3)2CHCl or CH3CH=CH2 4

step 2 heat with Al Cl3 + CH3COCl
step 3 NaOH + I2 (or Cl2) (then H+)
step 4 LiAl H4 (in dry ether)
8(b)(ii) step 2 electrophilic (aromatic) substitution 2

step 4 reduction
9(a)(i) n = (100 / 1.1)(8 / 100) = 7.3 ( 7 C atoms) 1
9(a)(ii) C7H7+ 1
9(a)(iii) F is C7H6O 2
G is C14H12O2

9701/41 Cambridge International AS/A Level – Mark Scheme October/November 2018
8
PUBLISHED
8 5(c) 2
M1 length of chain with both monomers [1]

M2 continuation bonds [1]
5(d)(i) C-C bonds are non-polar / have no dipole so cannot be hydrolysed [1] 1
5(d)(ii) M1 Hydrolysis using acid / base / alkali / enzymes [1] 2

M2 action of UV light [1]
Question Answer [W'18 P41Marks

Q5]
6(a) 2
M1 amide bond displayed [1]

M2 rest of the structure [1]

6(b)(ii) step I condensation [1] 9 2
step II reduction [1]
9 6(c) 2
• amide bond (CO-NH)

• structure of polymer with exactly two repeat units
• continuation bonds
• hydrocarbon portions correct
two points = [1]

four points = [1]
[W'18 P42 Q6]

9701/42 Cambridge International AS/A Level – Mark Scheme October/November 2018
10
PUBLISHED
10 7(a)(i) C15H10N2O2 1
7(a)(ii) 2
-NH-CO-O- linkage [1] whole molecule correct [1]
7(a)(iii) 2
intermolecular force group(s) involved
hydrogen bonding NH
VDW forces / Induced dipole-dipole -C6H4CH2- allow benzene / aromatic rings

forces / polar forces
M1 hydrogen bonding [1]

M2 NH group for hydrogen AND second correct IMF [1]
7(b) 3
type of polymer example
synthetic polyamide nylon / Kevlar
synthetic polyester Terylene
conducting polymer polyacetylene / polyethyne
non-solvent based adhesive epoxyresins / superglue
one mark [1] for each correct answer up to a maximum of [3]
[W'18 P42 Q7]


11
PUBLISHED
11 5(a)(i) 2
NC
NC
CO2CH3 CO2CH3
M1 correct C–C backbone (with correct side groups)

M2 continuation bonds and two repeat units
5(a)(ii) addition 1
5(a)(iii) Any two of: 2

permanent dipole (attraction): C, N, O, OR CO, CN, CO2CH3, OCH3
H-bonding: N, O OR CO, CN
London/van der Waals: N, C, H, O OR CH3, CN, CO2CH3, C–C chains

5(b)(i) Y CH3COCO2CH3 2
Z CH3C(OH)(CN)CO2CH3
[M’19 P42 Q5]
5(b)(ii) M1/M2 step 1: CH3OH and (conc) H2SO4 + heat 4
M3 step 2: HCN + NaCN catalyst
M4 step 3: T > 100oC / heat with Al2O3 (or heat with c. H2SO4)

9(b)(ii) 1
12
or
12 9(c)(i)
-bonds only -bonds only both - and -bonds
1
bonds broken
bonds formed
Both ticks correct
9(c)(ii) 2
M1: amide link
M2: rest of the structure
9(d) 2
9701/41 Cambridge International AS/A Level – Mark Scheme May/June 2019

PUBLISHED
or CH3CCl=CH2 and C2H5CH=CHCH3 each correct structure scores one mark
9(e) C-C bonds are non-polar / polyalkenes cannot be hydrolysed and polyamides can be broken down by hydrolysis 1

9(f)(i) 1
[S’19 P41 Q9]
9(f)(ii) M1: step 1: CH3COCl + AlCl3 [1] 3
M2: step 2: NaBH4 / LiAlH4 [1]
M3: step 3: conc. H2SO4, heat [1]

9701/42 Cambridge International AS & A Level – Mark Scheme May/June 2020
13
PUBLISHED
13 6(a)(i) condensation 1
6(a)(ii) 1
6(a)(iii) id-id forces/London forces AND permanent dipole-dipole forces 1
6(b) M1 (secondary structure by) hydrogen bonding between CO and NH groups 2

[S’20 P42 Q6]
M2 (tertiary structure by) interactions between R groups and one example of a named intermolecular force
6(c) M1 (hydrogen bonding between) base pairs 2

M2 A with T and C with G
6(d) hydrolysis and by action of light/UV 1
6(e)(i) 2
Award one mark for each correct structure

14
Polymerisation WS 2
1
[W’02 P4 Q6]

K = CH3CONH2 [1]
4
15
2 (b) (i) condensation [1]
(ii) ClCOCH2CH2COCl + 2HOCH2CH2OH → [1]
HOCH2CH2OCOCH2CH2CO2CH2CH2OH (+ H2O) [1]
(c) (i) polyamide or nylon (allow condensation) [NOT peptide or protein] [1]
(ii)
HO2C CO2H (or dichloride) NH2(CH2)4NH2
[1] + [1]
3
[S’03 P4 Q5]
Total 10
6 (a) (i) 1s22s22p63s23p6 4s23d2 or [Ar] 4s23d2 (or vice versa) [1]
(ii) two of TiCl2, TiCl3, TiCl4 [1]
(b) (i) blue solution is formed [1]
containing [Cu(H2O)6]2+ [1]
(ii) NH3 replaces H2O ligands or forms [Cu(NH3)4]2+

(or [Cu(NH3)4(H20)2]2+ [1]
which is deep blue/purple [1]
Total 6
© University of Cambridge Local Examinations Syndicate 2003

16 2005
GCE A LEVEL – November 9701 4
53 (a) (i) addition (polymerisation) [1]
(ii) condensation (polymerisation) [1]
(b) hydrogen bonding [1]
(c) (i) HO2CCH2CH2CO2H [1]
(ii) ester (accept “covalent”) [1]
(d) (i) heat with H3O+ or heat with OH-(aq) [1]
(ii) H2N-CH2-CH(OH)-CH2-NH2 or H3N+-CH2-CH(OH)-CH2-NH3+ [1]
HO2C-CH(OH)-CH(OH)-CO2H or -O2C-CH(OH)-CH(OH)-CO2- [1]
(allow bonus mark if the acid/base forms are consistent with the reagent used for the
hydrolysis) [1]
4 max 3
(e) (i) NC-CH2-CO2- K+ [1]
(ii) II: H2 + Ni or Na in ethanol [allow LiAlH4] [1]
III: dilute HCl or H2SO4 or H+(aq) [1]
3
[W’05 P4 Q5]
total: 11
© University of Cambridge International Examinations 2005

[allow -CO2¯ for E] [5]
[Total: 5]
17
7
4 polymer addition/condensation? formulae of monomers
HO2C-CO2H or ClCO-COCl
1 condensation
NH2-CH2-CH2-NH2
HO-CH2-CH(C2H5)-CO2H
2 condensation
HO-CH2-CH(CH3)-CO2H
CH2=CH-CH3
3 addition CH2=CH-CONH2
CH2=CH-C6H5
⇑ ⇑
[2] [6]
(2 correct: [1]) (6 correct: [5])
etc
(2 correct: [1])
(C=C bonds not needed, but penalise –[1] if C-C drawn instead of C=C)
(if more than 7 formulae drawn, then penalise –[1] for each formula in excess of 7) [8]
[S’08 P4 Q7]
[Total: 8]
© UCLES 2008

Page 5 Mark Scheme: Teachers’ version Syllabus Paper
18
GCE A/AS LEVEL – October/November 2009 9701 41
55 (a) (i) I: KMnO4 [1]

heat with H+ or OH– [1]
II: SOCl2 or PCl5 or PCl3 (NOT aq) [1]
(ii) -[-CO-C6H4-CO-NH-C6H4-NH-]- (Peptide bond must be displayed for minm) [1]

[4]
(b) (i) CH3NHCO-C6H4-CONHCH3 (1 mark for each end) [1] + [1]
(ii) HOCH2CH2O-CO-C6H4-CO-OCH2CH2OH for [1]

or the polymer -[- OCH2CH2O-CO-C6H4-CO-]- for [2]
[4 max 3]
(c) (i) Cl– +NH3-C6H4-NH3+ Cl- (1 mark for each end) [1] + [1]
(ii) H2N-C6H2Br2-NH2 or H2N-C6H2Br3-NH2 or H2N-C6Br4-NH2 [1]

[3]
(d) I: HNO2 (or NaNO2 + HCl/H2SO4) [1]

at T < 10oC [1]
II: m-prop-2-yl phenol, (CH3)2CH-C6H4OH [1]

+ NaOH(aq) [1]
[4]
(e) (i) A species having positive and negative ionic centres / charges, with no overall charge [1]
(ii) -O2C-C6H4-NH3+ [1]

[2]
[W’09 P41 Q5]
[Total: 16]
© UCLES 2009

will become more negative (1) [5]
[Total: 11]
19
66 (a) (i) SOCl2 or PCl5 or PCl3 (1)
(ii) CH3CO2H + SOCl2 → CH3COCl + SO2 + HCl

or CH3CO2H + PCl5 → CH3COCl + POCl3 + HCl
or 3CH3CO2H + PCl3 → 3CH3COCl + H3PO3 (1)
[2]
(b) (i) A is C6H5CO2C2H5 (1)

B is C6H5CONH2 (1)
(ii) ester (1)

amide (1)
(iii) nucleophilic substitution / condensation (1) [5]
(c) (i) C is ClCOCOCl (1)

D is ClCOCOCOCl (1)
(ii) hydrogen bonding (1)
(iii) because it’s an amide or not an amine or its lone pair is delocalised (over C=O)
or less
available due to electronegative oxygen [NOT: E is neutral, but the diamine is
basic] (1)
(iv) condensation (polymer) or polyester (1) [5]

[S’10 P41 Q6]
[Total: 12]
© UCLES 2010

[2]
[Total: 9]
20
57 (a) acidities: CHCl2COGCE A LEVEL – May/June 2012
2H > CH2ClCO2H > CH3CO2H
9701 42 [1]
due to Cl being (more) electronegative/electron withdrawing (than H). [1]
(b) Page 7 Mark Scheme: Teachers’ version Syllabus Paper
this stabilises the anion or weakens the O-H bond [1]
first second GCE A LEVEL – May/June
test 2012 9701
observation 42
observation
[3]
compound compound with first with second
(b) compound compound
first second test observation observation
compound compound Br2(aq) [not (l)] with first decolourises/
with second
none
NH2 NH2 compound white ppt.
compound
NaNO 2 + HCl or HNO2
Br2(aq) [not (l)] none
decolourises/
yellow/orange/red
none white ppt.
NH2 followed by phenol (+ NaOH)
NH2 ppt.
NaNO2 + HCl or HNO2 (immediate) yellow/orange/red
none
AgNO 3(aq)
followed by phenol (+ NaOH) white ppt. ppt.none
(immediate)
steamy/misty/
AgNO
add 3(aq)
H2O/ROH none
none
white
whiteppt.
fumes
CH3CH2COCl CH3COCH2Cl
steamy/misty/
add H2O/ROH
(2,4-)DNPH none none
orange ppt.
CH3CH2COCl CH3COCH2Cl white fumes
(2,4-)DNPH
– none yellow
orange ppt.ppt./
I2/OH none
– yellow ppt./ smell
antiseptic
I2/OH none yellowsmell
ppt./
I2/OH –
none antiseptic
yellow ppt./ smell
antiseptic
I2/OH– none
Fehling’s/Benedict’s solution antiseptic smell
red ppt. none
Fehling’s/Benedict’s solution
+ warm
CH3CH2CHO CH3COCH3 red ppt. none
+ warm
CH3CH2CHO CH3COCH3 Tollens’ reagent + warm silver/black ppt. none
Tollens’
2–
reagent
+
+ warm silver/black ppt. none
Cr2O7 2–+ H ++ warm turns green no change
Cr2O7 + H + warm turns green no change
– +
MnO4 +
– H ++ warm decolourises no change
MnO4 + H + warm decolourises no change
threethree
correct reagents
correct reagents [3] [3]
threethree
correct positive
correct results
positive results [3] [3]
threethree
× ‘none’
× ‘none’ [1] [1]
[7] [7]

(c) condensation
(i) condensation [1] [1]
(c) (i)
(ii) (in parts (ii) and (iii), allow structural formulae instead of skeletal formulae) [1] + [1]
(ii) (in parts
or NaO(ii) and (iii), allow structural formulae instead of skeletal formulae) [1] + [1]
or NaO HO
or Cl or Cl
HO
and or HO
Cl OHor Cl
and HO OH
OH
or ONa O O
OH
E or ONa O O
F
(N.B. E
letters E and F may be reversed.) F
(N.B. letters E and F may be reversed.)
(iii) make acyl chloride from F (if not already there) [1]
add that to a solution of E in NaOH(aq) [1]
(iii) make acyl chloride from F (if not already there) [1]
add that to a solution of E in NaOH(aq) [1]
[S’12 P42 Q5]

21
GCE A LEVEL – October/November 2013 9701 41
58 (a) (i) many monomers form a polymer [1]
(ii) addition [1]
(iii) C=C/double/π bond is broken and new C-C single bonds are formed
or double bond breaks and forms single bonds with other monomers [1]
[3]
(b) propenoic acid [1]
[1]
(c) (i)
carbon chain and CO2H [1]

at least one sodium salt [1]
(ii) 120° to 109(.5)° [1]

due to the change from a trigonal/sp2 carbon to a tetrahedral/sp3 carbon [1]
[4]
(d) (i)
Any four:
hydrogen bond labelled
water H-bonded to O through H atom
δ+/δ- shown on each end of a H-bond
lone pair shown on O- or C=O or H2O on a correct H-bond
Na+ shown as coordinated to a water molecule [3]
(ii) Solution became paler and Cu(2+) swapped with Na(+)

or darker in colour and polymer absorbs water [1]
[4]

22
(e) (i) alkene(1), amide(1) [2]
(ii) NH3 [1]
(iii) H2O [1]
(iv) HCl (aq)/H3O+ and heat/reflux (not warm) [1]

or OH- (aq), heat and acidify
[5]
[W’13 P41 Q5]
[Total: 17]

23
GCE A LEVEL – May/June 2011 9701 42
49 (a) (i) (allow displayed, structural or skeletal formula)

OCOCH3 OCOCH3
chain [1]
repeat unit [1]
(ii) C should be CH2=CHOH (or skeletal formula) [1]
(iii) C is CH3CH=O (or skeletal formula) [1]
(iv) e.g. add (2,4-)DNPH or DNP or Brady’s reagent ecf [1]

orange or red ppt forms (NOT yellow) ecf [1]
(or could use Fehling’s or Tollens’,
or H+ + Cr2O72–: orange to green, or H+ + MnO4–: purple to colourless)
[6]
(b) (i) (allow displayed, structural or skeletal formula)
O O
O O
O O O
O O
D
correct repeat unit bracketed (any 3 atoms in chain) [1]
(ii) ester [1]
(iii) E is CH3CH2CH(OH)CO2H (or skeletal structure etc.)(2-hydroxybutanoic acid) [1]

allow ecf here from the formula of the repeat unit shown in (b)(i)
(iv) condensation (polymerisation) [1]
(v) they have the same “molecular” formula or C4H6O2 (do NOT allow empirical formula) or
same no. and type of atoms or same functional group or both are esters or they are
isomers [1]
[5]
(c) (i) optical isomerism (or chiral) [1]
(ii)
CO2H
CO2H
F G
(letters may be reversed)(allow ecf from E, also allow ecf for G from F) [1] + [1]
cis-trans or geometrical isomerism [1]

[4]
[Total: 15]
[S’11 P42 Q4]

24 – May/June 2015
Cambridge International A Level 9701 41
10 6 (a) (i) CH3COCl or ethanoyl chloride 1
(ii) electrophilic substitution 1
(iii) conc HNO3 and conc H2SO4 1
(iv) CHI3 1
(b) (i) 1
(ii) polyamide or condensation 1
(iii) H2O / water 1
(iv) Sn / Fe + HCl + conc / aq / heat/warm 1
(v) harder or more dense or stronger or higher m.pt or tougher or more rigid 1
due to cross-linking or more H-bonding between the chains
[Total: 10]
[S’15 P41 Q6]

25
GCE A/AS LEVEL – October/November 2008 9701 04
11
10 (a) (i) silkworm – hydrogen bonds [1]
spider – van der Waals’ OR hydrogen bonds [1]
(ii) spider silk is more elastic/flexible/less rigid than silkworm silk/has a lower density [1]
silkworm silk absorbs water more easily [1]
(iii) this increases the elasticity/hydrophobic nature of the silk [1]
(b) (i) a polymer formed with the elimination/formation of a small molecule

(or example) [1]
(ii) any addition polymer e.g. poly(ethene), PVC, etc. [1]
(iii) 3 from:
addition polymers have a limited range of bonds/monomers [1]
addition polymers are non-polar/have fewer/no H-bonds [1]
condensation polymers/proteins have a range of combinations of amino acids which give
a wide range of properties [1]
condensation polymers/proteins have more functional groups/sidechains [1]
different sequences of amino acids result in different 2°/3° structure [1]
[W’08 P4 Q10]
[Total: 12 max 10]
© UCLES 2008

[in each case, more than one spot circled or squared negates the mark] [3]
[Total: 11]
26
12
9 (a) (i) correct diagram showing at least one monomer unit, and at least one N-H and C=O.
i.e. –NH-C6H2-NH-CO– or –CO-C6H4-CO-NH–
(no mark for this, but apply a penalty of –[1] if candidate’s diagram does NOT show
these points correctly)
one H-bond between N-H of original chain and C=O group of new chain [1]
one H-bond between C=O of original chain and N-H group of new chain [1]
(ii) hydrogen bonds or H-bonds (in words; can be written on diagram)

(ignore ref to v d W) [1]
(iii)
HO2C CO2H or ClOC COCl [1]
allow HO2C- allow ClCO-

HOOC-
HOCO-
H2N NH2 [1]
allow NH2-
[5]
[S’09 P4 Q9]
© UCLES 2009

27
13
9 (a) (i) One [1]
(ii) Any alkene (or allow a cyclic amide, as in caprolactam) [1]
(b) Any TWO from: addition needs unsaturated/double bonds/alkene

condensation eliminates a small molecule
condensation needs a molecule other than a hydrocarbon
empirical formula of addition polymer is the same as that of its monomer
condensation needs two different functional groups
(NOT – “condensation needs two different monomers”) 2 × [1]
(c) (i) Water [1]
(ii)
O CH2
CH2 O
O O
Correct ‘ester’ bond [1]

‘sticks’ to rest of molecule [1]
Note : candidates need only show ‘brackets’ if more than one repeat unit shown
(iii) Polyesters [1]
(d) Monomers in Terylene have to alternate in order to condense out water (owtte) [1]
Alkenes can link in any order (and still form a polyalkene) (or diagram showing this) [1]
[S’11 P41 Q9]
[Total: 10]

28
14
8 (a)
traditional material modern polymer used
Paper/cardboard/wood/leaves PVC in packaging

hessian/hemp/jute
steel/aluminium
Cotton/wool/linen Terylene in fabrics
Glass/china/porcelain/earthenware Polycarbonate bottle

metal/leather
3 → 2 marks, 2 → 1 mark
[2]
(b) Reasons: Plastics/polymers pollute the environment for a long time do not decompose/
biodegrade quickly [1]
They are mainly produced from oil [1]
Produce toxic gases on burning [1]
max two
Strategy 1: Recycle polymer waste / use renewable resources [1]

Strategy 2: Develop biodegradable polymers [1]
[max 3]
(c) PVC [1]

Combustion would produce HCl / dioxins as a pollutant [1]
or
nylon/acrylic [1]
Combustion would produce HCN [1]
[2]
(d) (i) Polythene (or other addition polymer) [1]
(ii) Addition polymerisation [1]
The polymer chains don’t have strong bonds between them – easy to melt [1]
Could be answered with a suitable diagram [3]
[W’11 P42 Q8]
[Total: 10]

29
GCE AS/A LEVEL – May/June 2012 9701 41
15
8 (a)
LDPE HDPE minimum of 2 chains suitable sketches [1]

(The close packing of unbranched side chains means)
LDPE more space between the chains/polymers or HDPE less empty space between the
chains [1]
[2]
(b) van der Waals’ (VDW) forces [1]

are weaker [1]
[2]
(c)
Addition OR condensation
requires C=C/double bond does not need C=C/double bond
uses the same functional group needs two different functional groups
same general (empirical) formula as monomer different formula
no loss of small molecule/H2O/HCl small molecule /H2O/HCl is formed
Any two differences [1]

[2]
(d) (i) (through its long chain of) delocalised electrons/mobile electrons [1]
free electrons is not sufficient
(ii) planar [1]
the π bonds/p-orbitals overlap (with each other) [1]
(iii) C8H6
C4H3 [2]
[5 max 4]
[S’12 P41 Q8]
[Total: 10]

30
16
8 (a) A monomers: H2N–(CH2)6–NH2 and HO2C–(CH2)4–CO2H or ClCO(CH2)4COCl [1]
Condensation or nucleophilic substitution or addition-elimination [1]
B monomer: H2C=CHCH3 [1]
Addition (NOT additional) [1]
C monomer: H2N–(CH2)5–CO2H or H2N–(CH2)5–COCl or [1]
Condensation [1]
[max 5]
(b) (i) Need a statement from both columns for [1] mark.
(a) (b)
more compact packing in A stronger (inter-chain) forces in A

chains closer in A hydrogen bonding in A
chains further apart in B weaker (inter-chain) or van der Waals' forces in B
B contains side-chain/branched chains
[1]
(ii) Polymer B – van der Waals’/London (dispersion) forces/induced-instantaneous/induced

dipoles
NOT just 'dipole' [1]
[Total: 2]
[W’12 P43 Q8]
[TOTAL: 7]

[5]
[Total: 10]
31
17
8 (a) (i) It could denature the enzyme or
alter the 3D structure/tertiary structure/shape of active site. [1]
(ii) condensation [1]
[2]
(b)
[1]
[1]
(c) (i) (Acid present would) hydrolyse the ester (linkage) [1]
(ii) (Hot water would) soften (the container) [1]

GCE A LEVEL – October/November 2012 9701 41 [2]
(d) (i)
ester linkage shown [1]

rest of repeat unit correct (ONE) [1]
(ii) van der Waals’ from CH3/methyl group [1]
permanent dipole-dipole from ester group [1]
(iii) Accept any sensible physical property suggestion e.g. different melting point or different
density or different solubility. [1]
[5]
[W’12 P41 Q8]
[Total: 10]

32
18
8 (a) (i)
CO2H CO2H
CH CH2 CH CH2 [1]
(ii) Addition [1]
(iii) Hydrogen bonding [1]

[3]
(b) (i) more / increase water absorbing properties (allow attracts water more) [1]
more polar(ity)/more hydrophilic / has ionic side-chains (as well as hydrophilic ones) [1]
(ii) It should be biodegradable/decompose [1]

[3]
(c) idea of ion exchange / replacement of Na+ for Cd2+/Pb2+ [1]
(the metal ions) will be attracted to the carboxylate ions [1]

[2]
(d) (i) condensation [1]
(ii) OH/alcohol groups

so highly soluble / able to form hydrogen bonds [1]
[2]
[S’13[Total:
P41 Q8]
10]

33
19
8 (a) (i) CH2 = CH–CO2H or CH2 = CH–CO2R or CH2 = CH–COCl [2]
(ii) addition (polymerisation) [1]
(iii) C(CH2OH)4 [1]
(iv) water [1]

[5]
(b) (water is bonded to the polymer by) hydrogen bonding [1]

hydrogen bonds are weak or easily broken [1]
[2]
(c) (i) cross-linking causes no reduction in the number of –OH groups

or cross-linking molecules also have –OH groups [1]
(ii) property e.g. becomes harder / more rigid / less flexible / stronger / higher melting
point. [1]
because the chains are more strongly / tightly held [1]
[3]
[S’13 P42 Q8]
[Total: 10]

34
2
8. (a) (i) Any addition polymer (e.g. polyethene, polypropene, polystyrene, PVC,
0 PTFE, PVA, Teflon) [1]
(ii) Any condensation polymer (e.g. polyamide, polyester, nylon, Terylene, PET,
PLA, Kevlar, Nomex) [1]
(b) Hydrolysis or nucleophilic substitution [1]
Ester and amide / peptide or –CO2– and –CONH– [1]
2
(c)
O O CH3
O O
O or O
CH3 O O
Correct ester linkage [1]
CH3 side chain on only one monomer unit [1]
(d) Plant materials do not generally contain unsaturated hydrocarbons / alkenes /

C=C [1]
(e) (i) Y van der Waals’ forces [1]
Z hydrogen bonding [1]
(ii) Z, because it can form hydrogen bonds with water or it contains polar CO
and NH groups [1]
3
[S’14 P42 Q8]
[Total: 10]

receive / accepts a proton / H+ 1
2
1(e)(ii) H2NCH2CH2NH2 + 2HCl ClH3NCH2CH2NH3Cl
OR H2NCH2CH2NH2 + 2H +
H3N+CH2CH2N+H3 35 1
1
21 1(f)(i) amide bond, displayed or –CONH– 1
rest of the molecule with continuation bonds 1
O O
H H
N N
N N
H H
O O 2
1(f)(ii) condensation / addition – elimination 1

1
1(f)(iii) any named polyalkene / eg polyethene, PVC 1
allow Bakelite or Kevlar

1
[W’16
Total:P41 Q1]
20
© UCLES 2016

two further correct structures – 1 mark 1
(ii) 3-methylbutanal 1
(iii) pentanal 5 absorptions 1

2-methylbutanal 5 absorptions 36 1
dimethylpropanal 2 absorptions 1 [6]
22 9 (a) nylon, terylene – condensation; PVC – addition – all three correct 1 [1]
(b) correct fully displayed formula of -CO-NH- unit 1

correct polymer structure 1 [2]
H O O
N C N C
O O
H
N C N C
H H
(c) sequence / order of amino acids (in the polypeptide chain) [W’141 P43 [1]
Q9]
(d) hydrogen bond 1
C=O and N-H in two different amino acids in the backbone diagram 1 [2]

(ii) it is (highly) acidic or low pH or contains HCl (NOT contains enzymes) [1]
(iii) use hydrogels: of different (wall) thickness/strength (to release drug over time)
(iii) use hydrogels: of different chemical
of different composition (for different
(wall) thickness/strength breakdown
(to release drug over times)
time)
of different pores/holes
incorporating chemical composition (for different breakdown
(in their walls) (anytimes)
two) [1] + [1]
37 (in their walls)
incorporating pores/holes (any two) [1] + [1] [4]
[4]
2 (c) for the homopolymer, either using the amino acid the minimum is:
3
(c) for the homopolymer, either using the amino acid the minimum is:
-CO-CHR-NH-CO-CHR-NH-CO-CHR-NH-
-CO-CHR-NH-CO-CHR-NH-CO-CHR-NH-
or using the hydroxyacid the minimum is:
or using the hydroxyacid the minimum is:
CO2H CO2H
OCO2H CO2H
O CO2H O CO2H O CO2H
O O O CO2H O CO2H O CO2H
O O O or O O O
O O O O or O O O
O O
CO2H
CO2H
(–[1]
(–[1]for
foreach
eacherror)
error) [2]
[2]
for the
for heteropolymer, either
the heteropolymer, using
either thethe
using glycol compound
glycol and
compound andthe
thedi-acid
di-acidthe
theminimum
minimum is:
is:
OH OH
O O O O OO
O O O O or O O
O O O O or OO
O O OHOH O O OH
OH OO
(glycol)
(glycol) (di-acid)
(di-acid) (glycol)
(glycol) (di-acid)
(di-acid) (glycol)
(glycol) (di-acid)
(di-acid)
or using the amino

or using acidacid
the amino andand
thethe
di-acid, thethe
di-acid, minimum is:is:
minimum
(ester)(ester)
RO O R R R R O O COCO H
R 2H 2O O H H
O O N N
N N or or N N O O
N N H
H OH H H
O OH O O O R R
CO2HCO2H (amide) (ester)
(amide) (amide) (ester)
(amide)
(ester)
O (ester) R R O (amide)
O O O CO H (amide)
or O
O
O
O O CO2H2 O O H
H
or N or N O
N O
O N H
H or
O
O
O R O CO2H
CO2H CO2H
CO2H (amide)CO2H (ester)R O CO2H
(amide) (ester)
(A heteropolymer incorporating all three monomers can also be drawn. This should include an ester
(A heteropolymer
linkage between incorporating
the glycol andallone
three monomers
of the can and
CO2H groups, alsoanbeamide
drawn. Thisbetween
linkage should the
include an ester
aminoacid and
linkage between
another CO2the glycol Deduct
H group. and one[1]ofmark
the CO 2H the
from groups,
wholeandof an amide
section (c)linkage between
if complete the aminoacid
compounds and
are shown
another COthan
rather 2H group. Deduct
sections [1] mark
of chains. Allowfrom the wholesections
4-monomer of section (c) ifofcomplete
instead compounds
3. Allow [2] marks forare shown
a polymer
rathersection
than sections
even if oneof end
chains. Allow 4-monomer
is incomplete sections
(e.g. is lacking instead atom),
an oxygen of 3. Allow [2] marks
but if both for a
ends are polymer
incomplete
section even[1])
deduct if one end is incomplete (e.g. is lacking an oxygen atom), but if both(–[1] endsforare incomplete
each error) [2] [4]
deduct [1]) (–[1] for each error) [2] [4]
[S’0810
[Total: P4max
Q10]9]
[Total: 10 max 9]
© UCLES 2008
© UCLES 2008

38 – May/June 2015
Cambridge International A Level 9701 42
92 (a) [3]
4 monomer addition condensation both
(b) polythene is non-polar or its bonds are non-polar [2]

so not (easily) hydrolysed
(c) (i) [1]
O O
O
or NOT
OH Cl
OH
OH OH
Cl
(Allow displayed, skeletal, part-skeletal, structural etc.)
(ii) The ester (or –COO–) linkage / bond is hydrolysed or reacts with water [1]
(d) Polythene has (weak) van der Waals’ (or id–id) forces [3]
PVC has stronger van der Waals’ forces or additional dipole forces
Nylon has (strong) hydrogen bonding
[S’15 P42 Q9]
[Total: 10]

Cambridge International AS/A Level – March 2016 9701 42
39
Question Answer Mark
2 9 (a) (i) polyester : Terylene / polylactic acid (PLA) / 1
5 polyamide : nylon / Kevlar / Nomex
(ii) water or hydrochloric acid / hydrogen chloride 1
(b) (i) 2
polymer biodegradable
A yes
B yes
C no
D yes
(ii) 2
or equivalent 1,4-diacyl chloride

HOCH2CH2OH and
or equivalent 1,4-diester
(c) (i) V: [M’16 P42 Q9]

1
it has two amine / NH2 groups (which can be protonated) or
it has an amine / NH2 group on its side chain / R group
(ii) four (TT, TU, UT, UU) 1
(iii) hydrogen bonds; 2

between the O / N atoms or named group (in the polypeptide) and water;
or
ion-dipole attractions;
between NH3+ / CO2– and water;

20 Polymerisation MS Unlocked

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20 Polymerisation MS Unlocked

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Answer Mark

1(e)(i) lone pair 1 1

1(e)(ii) H2NCH2CH2NH2 + 2HCl

OR H2NCH2CH2NH2 + 2H+ H3N+CH2CH2N+H3 1

1 1(f)(i) amide bond, displayed or –CONH– 1

rest of the molecule with continuation bonds 1

1(f)(ii) condensation / addition – elimination 1

1(f)(iii) any named polyalkene / eg polyethene, PVC 1

allow Bakelite or Kevlar

Bilal Hameed Polymerisation 1

(ii) water or hydrochloric acid / hydrogen chloride 1

or equivalent 1,4-diacyl chloride

(ii) four (TT, TU, UT, UU) 1

(iii) hydrogen bonds; 2

[M’16 P42 Q9]

© Cambridge International Examinations 2016

Polymerisation 1 Bilal Hameed

7(b)(i) H+(aq) + heat 1

7(c)(i) white precipitate 1

7(c)(ii) C14H19O6N + 3NaOH C14H16O6NNa3 + 3H2O 2

7(d)(i) no change / colour remains orange 1

© UCLES 2017 Page 10 of 12

Bilal Hameed Polymerisation 1

4 5(a) nitrile; alkene; chloro; benzene / arene 2

[W'17 P41 Q5]

© UCLES 2017 Page 7 of 13

Polymerisation 1 Bilal Hameed

5 3(d) ester and hydrolysed 1

[W'17 P42 Q3]

4(a)(i) Eocell = 1.00 – (–0.26) = (+)1.26 V 1

4(a)(ii) VO2+ + V2+ + 2H+ VO2+ + V3+ + H2O 1

solutions labelled correctly in one half-cell [1]

© UCLES 2017 Page 6 of 12

Bilal Hameed Polymerisation 1

6 7(a)(i) CaC2 + 2H2O C2H2 + Ca(OH)2 1

7(c)(i) delocalised electrons 1

2 curly arrows [1]

7(d)(ii) nucleophilic addition 1

7(e) CH3CHO HCO2H CH3COCH3 HO2CCO2H 4

[W'17 P42 Q7]

© UCLES 2017 Page 10 of 12

Polymerisation 1 Bilal Hameed

7(a)(ii) • for addition polymerisation: 2

7(b)(i) (RCO2H + H2NR' ) RCONHR' + H2O 1

7(b)(ii) broken: C-O, N-H 2

7(b)(iii) bonds formed: 305 + 460 or 765 2

7(c) (If G = 0, then) H = T S 2

7(d)(i) heat with (conc.) KMnO4 1

7(e) intermolecular force group(s) involved 2

Question Answer [M’18 P42Marks

8(a)(ii) C=O 1670–1740 2

8(b)(i) step 1 heat with Al Cl3 + (CH3)2CHCl or CH3CH=CH2 4

8(b)(ii) step 2 electrophilic (aromatic) substitution 2

Question Answer Marks

9(a)(i) n = (100 / 1.1)(8 / 100) = 7.3 ( 7 C atoms) 1

© UCLES 2018 Page 9 of 10

Bilal Hameed Polymerisation 1

M1 length of chain with both monomers [1]

5(d)(ii) M1 Hydrolysis using acid / base / alkali / enzymes [1] 2

Question Answer [W'18 P41Marks

M1 amide bond displayed [1]

© UCLES 2018 Page 10 of 14

Polymerisation 1 Bilal Hameed

• amide bond (CO-NH)