MAKTAB SULTAN ABU BAKAR

UJIAN PENILAIAN PRA-PENTAKSIRAN SEM 3 2014

SUBJECT : CHEMISTRY

Section A

[15 marks]

1 A 6 D 11 C
2 D 7 A 12 D
3 C 8 D 13 D
4 B 9 C 14 C
5 C 10 B 15 A

16. a) Each correct structure = 1 x 4
i.
ii.
iii.
iv.
b) Geometrical isomer present @ each C in C=C is
surrounded by 2 different atoms / group of atoms [1]

cis - isomer trans - isomer
(Structures [1] label cis trans [1] )

17. correct type of reaction [1] x 4 reagent [1] x 4
Type of reaction Reagent
I Free radical substitution Br
2
under UV / hv
ii. Elimination
Alumina @ conc. H
2
SO
4

under heating
iii. Oxidation
Cold, dilute KMnO
4
/H
+

@ OH
-
iv. Nucleophilic substitution
Ethanolic conc. NH
3

under reflux

18. a) i. Calculate mole [1] ; stating empirical formula [1]
Element Carbon, C Hydrogen, H
Mass 92.3 7.7
Mole 92.3/12 = 7.7 7.7 / 1 = 7.7
Mol ratio 7.7 / 7.7 = 1 7.7 / 7.7 = 1
Empirical formula = CH
ii. (CH)
n
= 104 ; (13)

x n = 104 ; n = 8
Molecular formula = C
8
H
8
[1] Structure [1]

iii. Major [1] Minor [1] (no label only 1)

iv. to produce polystyrene / container.
18 .b) Each structure = 1 m x 8
A : CH
3
CH
2
Cl / AlCl
3
B : Cl
2
; uv
C :
D : I
2
in NaOH
E :
F : CH
3
COCl / AlCl
3

G : CH
3
Cl / AlCl
3

H :

19. a) m1 : Mechanism : S
N
2 [1]
m2 : Nucleophile : CN
-
. [1]
m3 : Structure : CH
3
CH
2
CH
2
CH
2
Cl [1]
m4 : and CH(CH
3
)
2
CH
2
Cl [1]
m5 - m8 refer to diagram below [4]

b) i. rate = k[CH
3
CH
2
CH
2
CH
2
Cl][CN
-
] / CN
-
is first order [1]
- increasing CN
-
will increase the rate of reaction [1]
ii. - rate of reaction increased [1]
Since C-Br bond length is longer / bond strength weaker [1]
c) m1 : 2-chloro-2-methylpropane [1] m2 : [1]
m3 : steric hindrance [1]

20.a) m1 : Acidity decrease according to order [1]

m2 : cyclohexane is electron-donating / positive inductive [1]
m3 : caused alkoxide more readily to accept proton @ cause
equilibrium shift to left [1]
m4 : benzene is electron withdrawring / negative inductive [1]
m5 : caused phenol more readily to donate proton @ caused
equilibrium shift to right [1]
m6 : NO
2
gives negative inductive / electron withdrawing /
stabilised phenoxide ion formed [1]



















20. b) Alternative 1 : Reagent : acidified KMnO
4
/ H
+
[1]
Observation : purple colour decolourised by cyclohexanol but
not by phenol [1]
Equation : [1]

Alternative 2 : Reagent : bromine water [1]
Observation : brown colour decolourised and white precipitate
is formed when added to phenol [1]
Equation : bromination of phenol [1]

20 c) m1 : Saytzeff rule : in elimination of H-X or H
2
O, H is
preferable to eliminate from neighbouring C with less H [1]
m2 : reagent : alumina / conc. H
2
O under heating [1]
m3 : Structure of 2,3-dimethylpentan-3-ol [1]

m4 ; m5 ; m6 - 3 products of dehydration [3]