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Chemistry A
Advanced GCE
Unit F324: Rings, Polymers and Analysis
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This mark scheme is published as an aid to teachers and students, to indicate the requirements of
the examination. It shows the basis on which marks were awarded by Examiners. It does not
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commenced.
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F324
Answer
CH3
January 2011
CH3
CH3
NO2
curly arrow
from ring
to NO2+
NO2
correct intermediate
curly arrow from
CH bond back to
reform ring
NO2
correct
products
H
NO2
CH3
CH3
+ H+
+
Question
1 (a)
Mark Scheme
NO2+
NO2
NO2
F324
Question
1 (b
)
Mark Scheme
January 2011
Mark
Answer
CH3
CH3
Guidance
ALLOW any correct unambiguous structures
ALLOW NO 2
NO2
NO2
NO2
(c)
2
ANNOTATIONS MUST BE USED
1st stage
isomer: isomer 3
product:
CH3
H2N
NH2
equation:
CH3
CH3
12 [H]
O 2N
NO2
4 H 2O
H2N
NH2
F324
Mark Scheme
January 2011
Mark
Question Answer
(c) (i) 2nd stage
organic compound: HOOCCH 2 COOH
Guidance
HO
DO NOT ALLOW molecular formula
OH
C
O
12
F324
Mark Scheme
Question
(a)
Answer
propane-1,2,3-triol
January 2011
Mark
1
Guidance
ALLOW absence of e after propan
ALLOW 1,2,3-propanetriol
ALLOW absence of hyphens
1, 2 and 3 must be clearly separated:
ALLOW full stops: 1.2.3 OR spaces: 1 2 3
DO NOT ALLOW 123
(b)
(i)
methanol OR ethanol
AND
(b)
(ii)
renewable
F324
Question
(c)
Mark Scheme
Answer
CH 3 CH 2 COOH + CH 3 CH 2 OH CH 3 CH 2 COOCH 2 CH 3 +
H2O
(CH 3 CH 2 CO) 2 O + CH 3 CH 2 OH
CH 3 CH 2 COOCH 2 CH 3 +
CH 3 CH 2 COOH
January 2011
Mark
Guidance
ALLOW correct structural OR displayed OR skeletal formula
ALLOW combination of formulae as long as unambiguous
DO NOT ALLOW molecular formulae
F324
Question
(d)
Mark Scheme
January 2011
Answer
Mark
A
C
O
H 2C
O
O
H 2C
C
H2
OR
OR
OR
O
CH3
HO
CH
CH2 COOH
H2 C
HC
CH3
O
CH
O
CH2 C
H3C
OR
C2H5
HO
OR
O
CH
CH COOH
OR
CH2
CH
C
O
OR
CH
C
O
H2 C
OR
CH3
CH2
CH3
CH
OR
OR
CH3 O
H3C
O
HO
COOH
H3C
CH3
CH3
Total
O
CH
COOH
C2H5
OR
H 3C
CH3
HO
OR
C 2H 5
Guidance
Mark A, B and C
independently ie
A can be any of the
alternatives in the 1st
column
B can be any of the
alternatives in the 2nd
column
C can be any of the
alternatives in the 3rd
column
F324
Question
(a)
Mark Scheme
Answer
observation: silver OR Ag
January 2011
Mark
ALLOW redox
CH3
Guidance
ALLOW black OR grey
OH
CH3
(b)
O
H
H
R
OH (+ OH
intermediate
products
IGNORE missing OH
DO NOT ALLOW incorrect second product
F324
3
Question
(c)
Mark Scheme
January 2011
Mark
Answer
reagent: Br 2
Guidance
DO NOT ALLOW ECF from incorrect reagent, eg 2,4-DNP
organic product:
H3C
CH3
H
3
C
Br
Br
Br
H3C
CH3
H3C
OR
Br
H
C
CH3
CH3
CH3
Br
Br
CH3
Br
Br
10
F324
Mark Scheme
Question
(a) (i)
Answer
ClCH(CH 3 )COOH + 3NH 3 H 2 NCH(CH 3 )COO + NH 4 + + NH 4 Cl
January 2011
Mark
1
Guidance
ALLOW use of two NH 3 :
ClCH(CH 3 )COOH + 2NH 3 H 2 NCH(CH 3 )COO + NH 4 + +
HCl
ALLOW products as above OR H 2 NCH(CH 3 )COOH +
NH 4 Cl
ALLOW use of one NH 3 :
ClCH(CH 3 )COOH + NH 3 H 2 NCH(CH 3 )COO + H+ +
HCl
ALLOW products as above OR H 2 NCH(CH 3 )COOH + HCl
For alternatives below,
for NH 4 Cl, ALLOW NH 4 +Cl OR NH 4 + + Cl
for HCl, ALLOW H+Cl OR H+ + Cl
for H 2 NCH(CH 3 )COO + NH 4 +
ALLOW H 2 NCH(CH 3 )COONH 4 + OR
H 2 NCH(CH 3 )COONH 4
ALLOW R in equation in place of CH 3 (either or both sides)
ALLOW correct structural OR displayed OR skeletal formula
ALLOW combination of formulae as long as unambiguous
DO NOT ALLOW molecular formulae
(a)
CH3
(ii)
HOOC
C
H
CH3
N
H
C
H
COOH
H 2N
C
H
COO
C
H
COOH
F324
4
Mark Scheme
Question
(b) (i)
January 2011
Mark
Answer
O
OR
OH
(b)
HO
CH2COOH
(ii)
C
H 2N
Guidance
COOH
H
CH2COOH
HOOC
H
C
NH2
(c)
Disadvantages
Any two from:
(one stereoisomer might have harmful) side effects
reduces the (pharmacological) activity/effectiveness
cost OR difficulty in separating stereoisomers
Synthesis of a single optical isomer
Any two from:
using enzymes or bacteria
using a chiral catalyst
OR transition metal complex/transition metal catalyst
using chiral synthesis
OR chiral starting material
OR natural amino acid
Total
10
2 max
2 max
8
F324
Mark Scheme
Question
(a)
(i)
Answer
Adsorption (onto the stationary phase)
Mark
(a)
(ii)
(a)
(iii)
(b)
(i)
(ii)
(iii)
January 2011
Guidance
ALLOW adsorbtion or adsorb(s) or adsorbed spelled
correctly at least once
DO NOT ALLOW anything that begins with ab...
ALLOW any value in the range 0.1 0.3
IGNORE significant figures
DO NOT ALLOW fraction/percent as final answer
ALLOW compounds have similar R f values/adsorptions
OR compounds have not (fully) separated
OR B is spread over a large region
OR compounds are similar
IGNORE retention times
ALLOW chromatography for GC
ALLOW they have different retention times
AND
MS is compared to a database/reference
(iv)
11
F324
Mark Scheme
Question
January 2011
Mark
Answer
Guidance
(b)
OH
(v)
*
*
(c)
Total
12
12
F324
Question
(a)
Mark Scheme
Answer
Mark
January 2011
Guidance
ANNOTATIONS MUST BE USED
ALLOW pentet
OR a response that implies a splitting into five
OR multiplet
ALLOW 1 mark for singlet and triplet and
quintet/pentet/multiplet with no identification of protons
Any suggestion that the oxygens cause a splitting scores a
maximum of 2 marks.
All 3 remaining splitting patterns correct 2 marks.
Any 2 correct 1 mark.
IF number labels for protons in diagram are not identified,
ALLOW identification by chemical shifts for 2 marks max:
singlet at 3.34.2 AND a triplet at 3.34.2
quintet/pentet/multiplet at 0.72.0
Clear and unambiguous identification of the protons other than
by position number should be credited, ie
CH 2 between two oxygens
13
F324
6
Question
(b)
Mark Scheme
Answer
ANY 5 marks plus correct structure (in box)
Mark
January 2011
Guidance
ANNOTATIONS MUST BE USED
Fragment peak at 91 is C 6 H 4 CH 3 + /C 6 H 5 CH 2 +
ALLOW C 6 H 4 CH 3 /C 6 H 5 CH 2
ALLOW peak at 91 represents loss of CH 3
Molecular formula is C 8 H 10
(or implied, ie any one of the structures below)
CH3
CH3
CH3
C2H5
CH3
CH3
CH3
13
14
F324
6
Question
(b)
Mark Scheme
Answer
Mark
January 2011
Guidance
CH3
C2H5
CH3
CH3
4 peaks
3 peaks
6 peaks
6
CH3
Total
15