M1.

(a) (i)

Allow CO2- and NH2+

1

(ii) NOTE − Two marks for this clip

M1 for alanine section bonded through N
M2 for alanine section bonded through C
But penalise error in proline ring
1

Allow MAX 1 for correct tripeptide in polymer structure

1

(b) (i) 3-methylpent-2-ene

Ignore E-Z, commas, spaces or missing hyphens
1

(ii) 4-amino-3-methylbutanoic acid

Ignore commas, spaces or missing hyphens
1

(iii)

or any polyamide section containing

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 8 carbons plus two C=O plus two N-H, such as

Trailing bonds are required

1

(iv) Non polar OR no polar groups / bonds (for attack by water / acids /
alkalis / nucleophiles or for hydrolysis)

C-C bonds are strong

1
[7]

M2.(a) Alkenes
1

Correctly drawn molecule of cyclobutane or methyl

cyclopropane, need not be displayed formula
1

(b) C6H14 (or correct alkane structure with 6 carbons)

Allow hexane or any other correctly named alkane with 6
carbons
1

(c) Poly(but-2-ene)
1

(d) High pressure

Allow pressure ࣙ MPa
Mention of catalyst loses the mark

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 1

(e) This question is marked using levels of response. Refer to the Mark Scheme
Instructions for Examiners for guidance on how to mark this question.

Level 3

All stages are covered and the explanation of each stage is generally correct
and virtually complete.

Answer communicates the whole process coherently and shows a logical

progression from stage 1 and stage 2 (in either order) to stage 3.
5–6 marks

Level 2

All stages are covered but the explanation of each stage may be incomplete or
may contain inaccuracies OR two stages are covered and the explanations
are generally correct and virtually complete.

Answer is mainly coherent and shows progression. Some steps in each stage
may be out of order and incomplete.
3–4 marks

Level 1

Two stages are covered but the explanation of each stage may be incomplete
or may contain inaccuracies, OR only one stage is covered but the
explanation is generally correct and virtually complete.

Answer includes isolated statements but these are not presented in a logical
order or show confused reasoning.
1–2 marks

Level 0

Insufficient correct chemistry to gain a mark.

0 marks
Indicative chemistry content
Stage 1: consider effect of higher temperature on yield
(Or vice versa for lower temperature)
• Le Chatelier’s principle predicts that equilibrium shifts
to oppose any increase in temperature
• Exothermic reaction, so equilibrium shifts in
endothermic direction / to the left
• So a Higher T will reduce yield

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 Stage 2: consider effect of higher temperature on rate
(Or vice versa for lower temperature)
• At higher temperature, more high energy molecules
• more collisions have E>Ea
• So rate of reaction increases / time to reach
equilibrium decreases
Stage 3: conclusion
Industrial conditions chosen to achieve (cost-effective)
balance of suitable yield at reasonable rate
[11]

M3.(a) (i)

These four only

1

(ii)

Allow − NH3+ and +NH3−

1

(iii) 2-amino-3-hydroxybutanoic acid

Ignore 1 in butan-1-oic acid

Do not penalise commas or missing hyphens

Penalise other numbers
1

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 (iv)

Allow –NH3+ and +NH3−

1

(b) (i) Condensation

Allow polyester
1

(ii) propane-1,3-diol
Must have e
Allow 1,3-propanediol
1

(c) (i) Addition

Not additional
1

(ii)

Allow monomers drawn either way round

Allow bond to F in CF3
1

OR

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 1 for each structure within each pair
1

(d) c
If wrong, CE = 0
1

C-C or C-F bonds too strong

1
[11]

M4.(a) Nucleophilic addition

1

M4 for lp, arrow and H+

Allow C2H5− for CH3CH2−

• M1 and M4 include lone pair and curly arrow.

• Allow: CN− but arrow must start at lone pair on C.
• M2 not allowed independent of M1, but allow M1 for
correct attack on C+.
• + rather than δ+ on C=O loses M2.
• Penalise incorrect partial charges.
• M3 is for correct structure including minus sign but lone
pair
is part of M4.
• Penalise extra curly arrows in M4.
4

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 (b) (i) M1

M1 for correct structure of product of part (a).

Allow C2H5− for CH3CH2−.
Penalise wrongly bonded, OH or CN or CH2CH3 once only in
clip.
1

M2

M2 cannot be gained by simply swapping two or more

groups with no attempt to show a mirror image., e.g. do not
allow M2 for

because these do not show the enantiomers as mirror

images.

Students must show an attempt at mirror images, eg allow

ie vertical groups same and horizontal swapped as if there was a mirror

between them

No mirror need be shown

Do not penalize wedge bond when wedge comes into contact with both
C&N
However these two could score M2 if placed as below as if
with a “mirror” horizontally between them.

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 1

(ii) M1 (Plane) polarized light

M2 only scores following correct M1
1

M2 Rotated in opposite directions (equally) (only allow if M1 correct

or close)
Not just in different directions but allow one rotates light to
the left and one to the right.
Not molecules rotate.
1

(c) 2-hydroxybutane(-1-)nitrile
1

(d) Weak acid / (acid) only slightly / partially dissociated / ionised

Ignore rate of dissociation.
1

[CN−] very low

Allow (very) few cyanide ions.
Mark independently.
1

(e) (i) H2C=CH−CH3 + NH3 + O2 H2C=CH−CN + 3H2O

OR

H2C=CH−CH3 + NH3 + 3O2 H2C=CH−CN + 3H2O2

OR doubled.
Allow C3H6 and CH2CHCN or C3H3N on this occasion only.

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 1

(ii)

Ignore n.
Must show trailing bonds.
Do not penalise C–NC bond here on this occasion.

Must contain, in any order,

3 of

Allow

and one of

Allow –CH2CH(CN)CH2CHCl− etc.

1

(iii) Addition (polymerization)

Allow self-addition.
Do not allow additional.
1
[15]

M5.(a)

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 Addition
1

(b)

(c) Q is biodegradable
1

Polar C=O group or δ+ C in Q (but not in P)

1

Therefore, can be attacked by nucleophiles (leading to breakdown)

1
[7]

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