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 18 .b) Each structure = 1 m x 8

A : CH3CH2Cl / AlCl3 B : Cl2 ; uv
i. D : I2 in NaOH
C:
ii. F : CH3COCl / AlCl3
E:

G : CH3Cl / AlCl3
H:

19. a) m1 : Mechanism : SN2 [1]

iii.
m2 : Nucleophile : CN-. [1]
m3 : Structure : CH3CH2CH2CH2Cl [1]
iv. m4 : and CH(CH3)2CH2Cl [1]
b) Geometrical isomer present @ each C in C=C is m5 - m8 refer to diagram below [4]
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 Br2 under UV / hv
Alumina @ conc. H2SO4 b) i. rate = k[CH3CH2CH2CH2Cl][CN-] / CN- is first order [1]
ii. Elimination - increasing CN- will increase the rate of reaction [1]
under heating
Cold, dilute KMnO4/H+ ii. - rate of reaction increased [1]
iii. Oxidation Since C-Br bond length is longer / bond strength weaker [1]
@ OH-
Ethanolic conc. NH3
iv. Nucleophilic substitution
under reflux
c) m1 : 2-chloro-2-methylpropane [1] m2 : [1]
18. a) i. Calculate mole [1] ; stating empirical formula [1] m3 : steric hindrance [1]
Element Carbon, C Hydrogen, H
Mass 92.3 7.7 20.a) m1 : Acidity decrease according to order [1]
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 m2 : cyclohexane is electron-donating / positive inductive [1]
ii. (CH)n = 104 ; (13) x n = 104 ; n = 8 m3 : caused alkoxide more readily to accept proton @ cause
Molecular formula = C8H8 [1] Structure [1] equilibrium shift to left [1]
m4 : benzene is electron withdrawring / negative inductive [1]
m5 : caused phenol more readily to donate proton @ caused
iii. Major [1] Minor [1] (no label only 1) equilibrium shift to right [1]
m6 : NO2 gives negative inductive / electron withdrawing /
stabilised phenoxide ion formed [1]
iv. to produce polystyrene / container.
20. b) Alternative 1 : Reagent : acidified KMnO4 / H+ [1] 20 c) m1 : Saytzeff rule : in elimination of H-X or H2O, H is
Observation : purple colour decolourised by cyclohexanol but preferable to eliminate from neighbouring C with less H [1]
not by phenol [1] m2 : reagent : alumina / conc. H2O under heating [1]
m3 : Structure of 2,3-dimethylpentan-3-ol [1]
Equation : [1]

Alternative 2 : Reagent : bromine water [1]

Observation : brown colour decolourised and white precipitate
is formed when added to phenol [1] m4 ; m5 ; m6 - 3 products of dehydration [3]
Equation : bromination of phenol [1]