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IR WS 1
1 B
2 C
3 C
4 B
5 C
6 C
7 C
8 B
9 C
10 D
11 A
12 C
13 A
14 C
15 C
16 C
17 B
18 A
19 D
20 D
21 B
22 B
Bilal Hameed IR 1
2
Page 8
IR WS 2
Mark Scheme Syllabus Paper
Cambridge International AS/A Level – March 2016 9701 22
[10]
IR 2 Bilal Hameed
Page 6 Mark Scheme Syllabus Paper
Page 6 Mark AS/A
Cambridge International Scheme
Level – May/June 2016 Syllabus
9701 Paper
21
Cambridge International AS/A Level – May/June 2016 9701 21
Question Mark Scheme Mark Total
Question Mark Scheme Mark Total
(d)
(d)
B is CH2=CHCH2CH3 OR CH3CH=CHCH3 OR (CH3)2C=CH
B is CH2=CHCH2CH3 OR CH3CH=CHCH3 OR (CH3)2C=CH2
3 2 [1]
[1]
distinguished by addition of bromine [1] [3]
distinguished by addition of bromine [1] [3]
brown/red/orange/yellow to colourless/decolourises with B (but not A) [1]
[2]
[2]
M1 = lone pair on C of CN− AND curly arrow from lone pair to C of C—Br [1]
M1 = lone pair on C of CN− AND curly arrow from lone pair to C of C—Br [1]
M2 = correct dipole on C—Br, curly arrow from C—Br bond to Br AND Br− [1]
M2 = correct dipole on C—Br, curly arrow from C—Br bond to Br AND Br− [1]
(b) (i) reduction [1] [1]
(b) (i) reduction [1] [1]
(ii) disappearance of peak / dip / trough / absorption at 1680–1730 [1]
(ii) disappearance of peak / dip / trough / absorption at 1680–1730 [1]
due to (loss of) C=O [1]
due to (loss of) C=O [1]
OR [2]
OR [2]
peak at 3200–3650 [1]
peak at 3200–3650 [1]
due to (alcohol) O—H (formation) [1]
due to (alcohol) O—H (formation) [1]
Page 7 Mark Scheme Syllabus Paper
(c) (i) sodium/potassium hydroxide [1]
(c) (i) Cambridge International AS/A Level – May/June 2016
sodium/potassium hydroxide 9701 21 [1] [2]
aqueous [2]
aqueous [1]
Question Mark Scheme
© Cambridge International Examinations 2016 Mark Total
© Cambridge International Examinations 2016
(ii) ethanol [1] [1]
(ii)
[1] [1]
[15]
Bilal Hameed IR 2
4
Page 5 Mark Scheme Syllabus Paper
Cambridge International AS/A Level – May/June 2016 9701 22
[Total 9]
AND
(ensures aldehyde escapes) to avoid further oxidation / to avoid forming acid / as reflux causes further oxidation [1] [2]
IR 2 Bilal Hameed
1 [1] [3]
(iii) NO + 2
O2 → NO2
[1]
NO2 + SO2 → SO3 + NO
[1]
SO3 + H2O → H2SO4 / 2H+ + SO42– / H+ + HSO4–
(ii) one of the double-bonded C atoms / first C has 2H atoms attached ora [1] [2]
so no cis-trans / E-Z / geometric(al) isomerism possible
OR
no chiral C [1]
so mirror images superimposable / molecule not asymmetric
(iii) asymmetric / chiral C atom / carbon with four different groups / atoms attached [1] [1]
C C
H H
Br CH3 H3C Br
[14]
Bilal Hameed IR 2
1
T=
1
6
U=
IR 2 Bilal Hameed
4(b)(ii) 2C4H8O2 + Na2CO3 2C4H7O2Na + H2O + CO2 1
4(c)(i) triiodomethane 1
4(c)(ii) F = CH3CH2CH2COCH3 7 1
G = C2H5CH(CH3)CHO 1
4(c)(iii) a (tetrahedral) atom with four different groups / atoms / substituents attached 1
OR
6 2017 JUN P22
a carbon Q04
(atom) with four different groups / atoms / substituents attached
4(d)(i)
9701/22 H C=O (group / bond) AND O–H (group / bond) International AS/A Level – Mark Scheme
Cambridge May/June 20171
PUBLISHED
I C=O (group / bond) AND C–H (group / bond) 1
Question Answer Marks
I = methyl methanoate 1
Total: 23
Bilal Hameed IR 2
Question Answer Marks
4(a)(ii) initiation 4
HCl
propagation 8
7 2018
4(b) MAR P22 Q04
elimination 1
4(c)(ii) cyclohexene would have absorption at 1500–1680 (cm–1) because of C=C (and adipic acid would not) max 3
cyclohexene would have absorption at 3000–3100 (cm–1) because of =C—H/C—H in alkene (and adipic acid would not)
adipic acid would have absorption at 2500–3000 (cm–1) because of O—H/CO2—H (and cyclohexene would not)
adipic acid would have absorption at 1040–1300 (cm–1) because of C—O (and cyclohexene would not)
adipic acid would have absorption at 1640–1750 (cm–1) because of C=O (and cyclohexene would not)
IR 2 Bilal Hameed
9
4(d)(i) EITHER 2
Glycolic acid would have:
M1 2500–3000 due to RCO2 H
M2 range within 3200–3650 due to RO–H
OR
4(d)(ii) O 2
O O
O
Bilal Hameed IR 2
M3 –82.4 [1]
IR 2 Bilal Hameed
11
3(e) 3
P Q R
acidified
no reaction no reaction (turns) green
K2Cr2O7(aq)
3(c) M1 geometric(al) 2
M2
3(d) M1 compound P 3
4(a) 3-chloroprop-1-ene 1
Bilal Hameed IR 2
9701/21 Cambridge International AS/A Level – Mark Scheme October/November 2019
PUBLISHED
Question Answer Marks
12
4(b)(iv) 2
M1: / CH3CH(OH)CH3
4(c)(ii) Aldehyde 1
4(c)(iii) has a carbon / atom attached / bonded to four different atoms / groups / groups of atoms / chains 1
4(c)(iv) 2
4(c)(v) 1
principal absorptions in bond responsible
the infra-red spectrum
4(c)(vi) 3
© UCLES 2019 Page 8 of 9
OR
M1: skeletal alkene group AND C5 structure
M2: curly arrow from C=O bond to O AND intermediate with CN attached and –ve charge on the O
4(c)(viii) catalyst 1
IR 2 Bilal Hameed
Question Answer Marks
13
ONLY
M2: explain difference in reactivity in terms of positive inductive effect – comparative answer
lower (positive) inductive effect / lower (+)I
OR
inductive effect of less alkyl groups
Bilal Hameed IR 2
14
3(d)(i) M1 3
M2 (two) different groups on each C atom in the C=C / end of the C=C double bond
3(d)(ii) H2 / hydrogen 1
IR 2 Bilal Hameed
5(d)(i) Two structures representing the intermediate 2
M1 C2H5C+HCH3
M2 CH3CH2CH2C+H2
14 2020
QuestionJUN P21 Q06 Answer Marks
6(a) 1
6(b)(i)
9701/21 hot AND concentrated Cambridge International AS & A Level – Mark Scheme 1
May/June 2020
PUBLISHED
6(b)(ii) oxidation 1
Question Answer Marks
6(e) Predict two differences, with reasons, between spectra of Y, CH3CH2COCH3 and 2-methylbut-1-ene (shown) 2
first difference
M1 absence of peak/ absorption at 3100 (cm–1) as no longer any =C–H present (in Y)
second difference
M2 peak at 1650 (cm-1) moves to the left to any value / range of values between 1670 and 1740) due to disappearance of
C=C (in Y) and appearance of C=O (in Y)
OR
absence of peak at 1650 (cm-1) as no longer any C=C present (in Y)
AND
appearance of peak (in Y) at (any value / range of values) between 1670-1740(cm-1) due to C=O
6(f)(ii) propan-1-ol 1
ALLOW propan-2-ol as error carried forward from 6f(i)
Bilal Hameed IR 2
M2: TWO correct co-ordinate bonds identified
3(a)(ii) 120 16 1
15 2020
3(b) NOV P21
Al(OH) Q03hydroxide
/ aluminium 3 1
3(c)(ii) (M1: correct identity of R and statement re: reaction 3 ONLY ketone reduced) 2
3(c)(iii) 4
M1: Presence of :CN (if bonding shown, must be unambiguous triple bond)
M2: curly arrow from :CN lone pair to carbonyl carbon
M3: correct dipole AND curly arrow from double bond to oxygen
M4: correct intermediate drawn
IR 2 Bilal Hameed
4(c) 3
reagent result with P result with Q
16 2020 NOV
Award P22 Q04
one mark for every two correct observations.
4(d)(iii) C12H20O2 1
Bilal Hameed IR 2
18
5(b)(i) 2-bromobutane 1
5(b)(ii) substitution 1
5(b)(iii) reagent 1
M1 NaCN or KCN
conditions 1
M2 ethanolic AND heat (under reflux)
IR 2 Bilal Hameed
PUBLISHED
Question Answer Marks
3(c)(iii) 2
G = C2H5CH2OH H = C2H5CH=CHC2H5
19
3(d) 2
CH3CH2CO2H CH3COCH3
4(a)(iii) substitution 1
4(b) M1 ester 3
OR
4(c)(i) 1
OR Na+
Bilal Hameed IR 2
OR
OR OR
3(c)(i) 1
20
19 2021
3(c)(ii) NOV
sp P22 Q03
2 1
3(e)(ii) Iodine / I2 1
IR 2 Bilal Hameed