No Answer Scheme Mark

1 (a) q = mcT or 1
(i) = (2000)(4.18)(97-25)
= 601920 J (with unit) 1

82 % 609120 J
100% 734049 J 1

Number of mole butane = 15 / 58 = 0.259 mole 1

0.259 mole butane 734049 J

1 mole butane 2834166 J 1
= 2834 kJ

Standard enthalpy combustion of butane = -2834 kJ mol-1 1

(a)(ii) C4H10(g) + 13/2 O2(g) 4CO2(g) + 5H2O(l) H= -2834 kJ mol-1 1+1

(b)
(i) Q = It or 1
= (0.483 A)((1000s)
= 483 C 1
= 0.005 F
or

M x+ + xe M 1

1 mol M 48 g M x mol e- x F
48 g M xF
0.120 g M 0.005 F 1
OR
0.005 48
= =2
0.120

Oxidation number of M= +2 1

(b) Anode : 2H2O(l) O2(g) + 4e- + 4H+ (aq) 1

(ii)
1 mol O2 4 mol e 4 F
1
y mole O2 0.005 F

y = 0.00125 mol 1

Total 16
Max 15
No Answer Scheme Mark
2 (a) Rate = k [C3H7Cl][OH-] 1
(b) M-1 time-1 (note: time can be replaced by s , min, hour.) 1
(c) Rate = k (0.10M)(0.15M) 1
= 0.015k M time-1 1

(d) Method 1: doubled both concentrations of compound A 1

and sodium hydroxide

Method 2: quadrupled one of the concentrations of 1

reactant while another remain constant

(note: or any possible method that involves concentration change)

(e) CH3CH2CH2Cl 1

Compound A is primary haloalkane. Primary haloalkane is most 1
reactive in this reaction (SN2) because it has the least steric effect. 1

(f)

OH-
CH2CH3
CH2CH3
C Cl HO C Cl
H
H
H H

2 arrows 1M 5

3D-structure of RX 1M
CH2CH3
Activated complex structure 1 M
+ Cl-
HO C
H
3D-structure of product 1M
H
SCl- group 1M
N2as leaving
1
Total 15
No Answer Scheme Mark
3 (a) (i) (iii) 1+1
ONa

Cl
(iv)
(ii) O
1+1

(b) (i) Ethanol is a weak acid, cannot react with NaHCO3 (very weak 1
base) and release CO2 gas

(ii) cyclobutyl has greater hydrophobic area. 1

(iii) carboxylate ion is more stable than phenoxide ion by resonance

stabilisation in which ve charge delocalized between two O atoms 1
which is more electronegative.
Or in phenoxide ion, negative charge is delocalized into less
electronegativity C atom in benzene ring
.
(c) P: CH3CH2CHCH3 R: CH3CH2CH2COOH 1+1
(i)
OH
Q: CH3CH2CH2CN S: CH3CH2CH2CH2OH 1+1

(c) Reagent I : NaOH (aq), heat 1

(ii) Reagent II : PCC in CH2Cl2 1
(c)
(iii) activated complex
CH2CH3

NC C Br 3
H H
transition state
Total 16
Max 15
No Answer Scheme Mark
4 (a) Initiation Step
Marks are given to complete
uv equations with arrow.
Br Br 2Br 1

Propagation step

CH2
CH2
+ Br + HBr 1
H

CH2 CH2Br
1
Br Br + Br
+

Termination step

Br + Br Br2

CH2 CH2Br
+ Br
1
CH2 CH2 CH2CH2
+

(b) Function : as Lewis acid catalyst to produce electrophile 1

(i)
(b) Formation of electrophile
(ii)
Cl Cl + FeCl3 Cl Cl FeCl3 1
Formation of Arenium ion
Cl H Cl H Cl H

+ Cl Cl FeCl3
1
+ FeCl4

Deprotonation to retain aromaticity

Cl H Cl

+ Cl FeCl3 + HCl + FeCl3 1

(c)
O O
OH
> > 1

Reason:
Benzoic acid form more and strong hydrogen bonds through
dimerisation between molecules. 1
Benzaldehyde is a polar molecules whereas ethyl benzene is non
polar, Benzaldehyde forms stronger van der Waals forces between 1
them
(d)

CH3
CH2 CH3
HCl Cl
KCN
CN
alcohol

H2O/H+ 5

CH3
COOH

ALTERNATIVE ANSWER

CH3
CH2 CH3
HCl Cl
Mg
MgCl
dry ether
O (i) CO2
(i) H C H (ii) H2O/H+
(ii) H2O/H+

CH3
CH3
KMnO4/H + COOH
CH2OH

Total 16
Max 15
no answer marks
5
A: CH2 C: E:

5
B: D:
CH3
CH3

Reasons:
1. A,B and C are alkenes @ contain C=C because they decolourise Br2 in CH2Cl2 1
2. A,B and C are alkenes @ contain C=C because they are positive with Bayers 1
test
3. Oxidation of A and B determines/proofs the position of C=C in A and B 1
4. Ozonolysis of C determines/proofs the position of C=C in C 1
5. Catalytic hydrogenation of alkene produces alkane. 1

1
@ conc. H2SO4
CH2OH CH3 CH2
1
OH

Br
CH2Cl2
CH3 + Br2 CH3 1+1

Br

Br
1+1
CH3 + Br2(aq) CH3

HO

reagent for ozonolysis of C : i) O3 ii) Zn, H2O 1

Cl
HCl 1

Cl 1
H Cl
1
+ Cl-
1
H
TOTAL 21
MAX 20
no answer marks
6 a
Compound Structures
o-methylphenol OH Any
three
CH3 :
Propanoic acid O 2
CH3CH2C OH
2-flouropropanoic acid O

CH3CHC OH
F
2-chloropropanoic acid O

CH3CHC OH
Cl
4-methylcyclohexanol OH

H3C
Acidity:
4-methylcyclohexanol < o-methylphenol < propanoic acid < 1
2-chloropropanoic acid < 2-fluoropropanoic acid
Explanation: more stable the conjugate base (ion), the more acidic the acid.

Propanoate / carboxylate ion is more stable than o-methylphenoxide/ phenoxide ion 1

because electron/negative charge is delocalised/resonance into more electronegative
oxygen atoms in carboxylate ion.

In o-methylphenoxide / phenoxide ion, electron is delocalised / resonance into less 1

electronegative carbon atom in benzene ring.

Alkoxide ion is less stable than phenoxide. Alkoxide contain alkyl group which is 1
EDG. Thus electron is localised / confined at oxygen atom.(No resonance
stabilization)

2-chloropropanoate and 2-fluoropropanoate are more stable than propanoate ion 1

because F and Cl are EWG.

F is more electronegative than Cl, thus 2-fluoropropanoate is the most stable. 1


+ CH3CH2CH3 1
H3O
Mg

CH3CHCl CH3CHMgCl 1
dry ether
CH3 CH3
b i)CO2 1

ii) H3O+ 1
O CH3CHCOOH
i) HCH CH3 1
+
ii) H3O
1

1
CH3CHCH2OH
1
CH3
c i) Lucas test @ HCl, ZnCl2 1

Compound Observation and reaction
2-propanol
HCl, ZnCl2
CH3CHCH3 CH3CHCH3 + H2O
1
OH Cl
Solution turns cloudy within 5-10 minutes.

Propanal No observable change after 10 min 1

Propanone No observable change after 10 min

(ii)Fehlings test / Cu2+ complex, OH-, @ Tollens test, Ag[(NH3)]2+, OH- 1

Propanal O O
Cu2+ complex, OH-,
CH3CH2CH CH3CH2C O- + Cu+ (s) ppt 1

Brick red precipitate is formed
1
Propanone No observable change
OR
Ag[(NH3)]2+ complex,
O O
OH-
CH3CH2CH CH3CH2C O- + Ag (s) ppt

Silver mirror precipitate formed

TOTAL 22
MAX 20