UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS

GCE Advanced Subsidiary Level and GCE Advanced Level

MARK SCHEME for the May/June 2012 question paper

for the guidance of teachers

9701 CHEMISTRY
9701/22 Paper 2 (AS Structured Questions), maximum raw mark 60

This mark scheme is published as an aid to teachers and candidates, to indicate the requirements of
the examination. It shows the basis on which Examiners were instructed to award marks. It does not
indicate the details of the discussions that took place at an Examiners’ meeting before marking began,
which would have considered the acceptability of alternative answers.

Mark schemes must be read in conjunction with the question papers and the report on the
examination.

• Cambridge will not enter into discussions or correspondence in connection with these mark schemes.

Cambridge is publishing the mark schemes for the May/June 2012 question papers for most IGCSE,
GCE Advanced Level and Advanced Subsidiary Level syllabuses and some Ordinary Level
syllabuses.
 Page 2 Mark Scheme: Teachers’ version Syllabus Paper
GCE AS/A LEVEL – May/June 2012 9701 22

1 (a) (i) silicon/Si or phosphorus/P (1)

(ii) sodium or sulfur name required (1)

(iii) white solid formed/white fumes seen

chlorine gas decolourised
aluminium glows or burns any two (2)

(iv) 2Al(s) + 3Cl2(g) → Al2Cl6(s) or

2Al(s) + 3Cl2(g) → 2AlCl3(s)
equation (1)
state symbols (1)

(v) outer shell of electrons is full/has a complete octet or

valence shell of electrons is full/has a complete octet or
activation energy is too high or
ionisation energy is too high (1) [7]

(b) (i)
Does the chloride approximate pH of the
element
dissolve or react? resulting solution

Na dissolve 7

Al react 1 to 4

Si react 1 to 4

one mark for each correct answer (6 × 1)

(ii) hydrolysis (1) [7]

(c) (i) around the N atom there is only one lone pair
around the S atom there are two lone pairs both (1)

(ii) angle (a) or sulfur – no mark for this

because two lone pairs repel more than one lone pair or
lone pair-lone pair repulsions are stronger
than lone pair-bond pair repulsions (1) [2]

[Total: 16]

© University of Cambridge International Examinations 2012

 Page 3 Mark Scheme: Teachers’ version Syllabus Paper
GCE AS/A LEVEL – May/June 2012 9701 22

2 (a) CH3OH(l) + 3/2O2(g) → CO2(g) + 2H2O(l) (1)

the enthalpy change/heat change/heat evolved when
one mole of CH3OH (1)
is completely burned or
is burned in an excess of air/oxygen (1) [3]

(b) ∆Horeaction = –283 + 2(–286) – (–726) (1)

= –129 kJ mol–1 (1)
correct sign (1) [3]

(c) pressure
increases rate (1)
by increasing frequency of collisions or
by increasing concentration of reactants (1)

temperature
increases rate (1)
because more molecules have energy >Ea (1)

catalyst
increases rate (1)
by providing an alternative route of lower Ea (1) [6]

[Total: 12]

© University of Cambridge International Examinations 2012

 Page 4 Mark Scheme: Teachers’ version Syllabus Paper
GCE AS/A LEVEL – May/June 2012 9701 22

3 (a)
HO2CCH2CH(OH)CO2H

heat with CH3OH/H+ heat with CH3CO2H/H+

CH3O2CCH2CH(OH)CO2CH3 HO2CCH2CHCO2H

OCOCH3
A B

concentrated H2SO4

HO2CCH=CHCO2H

C
hot concentrated
MnO4–/H+ steam/H3PO4
cold dilute
MnO4–/H+
HO2CCO2H HO2CCH2CH(OH)CO2H

D E

HO2CCH(OH)CH(OH)CO2H

give one mark for each correct compound (6 × 1) [6]

(b) malic acid into C dehydration or elimination (1)

C into D oxidation (1)
C into E addition or hydration (1) [3]

(c) solvents or perfumes or flavourings (1) [1]

© University of Cambridge International Examinations 2012

Page 5 Mark Scheme: Teachers’ version Syllabus Paper
GCE AS/A LEVEL – May/June 2012 9701 22

(d) (i)

correct compound (malic acid) shown as a pair of enantiomers in 3D (1)

chiral carbon (*) atom correctly identified (1)
structure fully displayed (1)

(ii)

give one for each correct skeletal formula (1 + 1)

correct cis (or Z) and trans (or E) labels (1) [6]

37.5 4.17 58.3

(e) C : H : O = : :
12 1 16

= 3.13 : 4.17 : 3.64 (1)

= 1 : 1.33 : 1.16 (1)

= 6:8:7

empirical formula is C6H8O7 (1) [3]

[Total: 19]

© University of Cambridge International Examinations 2012

 Page 6 Mark Scheme: Teachers’ version Syllabus Paper
GCE AS/A LEVEL – May/June 2012 9701 22

4 (a)
reagent R2CHOH RCHO RCO2H RCO2R’ RCOR’

NaHCO3

Na

Cr2O72–/H+

give one mark for each correct tick (5 × 1) [5]

(b) (i) alcohol or ROH

not hydroxyl or phenol or –OH (1)

80
(ii) n(H2) = = 3.3 × 10–3 mol (1)
24000

n(H atoms) = 2 × 3.3 × 10–3 mol = 6.6 × 10–3 mol (1)

0.30
(iii) n(G) = = 3.3 × 10–3 mol
90

n(G) : n(H atoms) = 3.3 × 10–3 : 6.6 × 10–3

= 1:2
so each –OH group produces one H atom (1) [4]

(c) (i)

or or and ‘ketone’ (1)

(ii) G is HOCH2COCH2OH as the minimum (1)

allow the gem diol CH3COCH(OH)2 [2]

(d) (i) H is HO2CCOCO2H as the minimum (1)

(ii) J is HOCH2CH(OH)CH2OH as the minimum (1) [2]

[Total: 13]

© University of Cambridge International Examinations 2012