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TESTCODE02212010
FORMTP2008168 MA Y/JUNE2008

CARIBBEAN EXAMINATIONS COUNCIL

ADVANCED ~ROFICIENCYEXAMINATION
CHEMISTRY - UNIT 1:

PaperOl
90minutes

( 10JUNE2008(p.m.))

READ THE FOLLOWING DIRECTIONS CAREFULLY

I. In addition to this test booklet, you should have an answer sheet.

2. Each item in this test has four suggested answers lettered (A), (B), (C), (D). Read each item you are
about to answer and decide which choice is best.

3. On your answer sheet, find the number which corresponds to your item and shade the space having
the same letter as the answer you have chosen. Look at the sample item below.

Sampleltem

Which of the following is the HIGHEST energy transition in an organic compound?

-
(A) n to er Sample Answer
(B) n to 1t*
(C) CJ 'tO CJ*
(D)
-
1t 'tO 1t*

The best answer to this item is "er 'to er", so answer space (C) has been blackened.

4. Ifyou wanttochangeyouranswer, besuretoeraseyouroldanswercompletely and fill in your new

choice.
5. Whenyouaretoldtobegin,turnthepageandworkasquicklyandascarefullyasyoucan. Ifyoucannot
answer an item,omititandgoon to the next one. You can comeback to the harder item later. Your
score will be the total number ofcorrect answers.
6. You may do any rough work in this booklet.
7. Figures are not necessarily drawn to scale.
8. The use ofnon-programmable calculators is allowed.
9. Thistestconsistsof45 items. Youwillhave90minutestoanswerthem.
I0. Do not bc:.-0ncemed that the answer sheet provi des spaces for more answers than there are items in
this test.

DO NOT TURN TRIS PAGE UNTIL YOU ARE TOLD TO DO SO.

 -2-
1. Volatility of organic compounds depends on .llim_1 refers to the following structure.
the strength of the intermolecular forces
present. Which compound below would be
the MOST volatile? H H H H
I I I I
(A) CH,CH,CH,OH H-C-C-C-C-H
(B) CH,CH 2 CH 2CH, I I I
(C) CH,CH(CH,)CH, H H H
(D) CH,CH2CH 2COOH
H-C-H
I
H-C-H
I
H

i. The IUPAC name for the structure is

(A) 2 - ethyl butane

(B) 3 - ethyl butane
(C) 2 - methyl pentane
~ 3 - methyl pentane

3. Which of the following is a pair of optical isomers?

CH3 CH3
I I
{A) CH3 -C-OH HO-C-CH,
I I
CH3 CH,

H
I
y.< C2H,-C-OH
I
CH3

H H H H H H H H
.I I I I I I I I
(C) H-C-C-C~C-CH HO-C-C-C-C-H
I I I I I I I I
H H H H H H H H
CH3 H H CH3
I I I I
{D) H-C-C-OH HO-C-C-CH3
I I I I
CH3 H H CH,
 -3-

4. Which of the following is NOT true of addition polymerization?

(A) Only one type of polymer is formed.

(B) The molecular mass of the polymer is a multiple of the
monomer unit.
!.CY The polymer is readily hydrolysed to the monomer.
(D) The physical and chemical proJlerties of the polymer
are different from those of th~ monomer.

~refers to the addition polymer represented by the

following chain sequence.

CH3H C2HsH Cl H
I I I I I I
-C-C-C-C-C-C-
I I I I I I
H Cl Br H H CH3

5. The monomers are MOST likely

CH 3 H C2Hs H
/ /
(A)
'/ C=C and
'\
/
c=c
H ' Cl H ' Cl

CH 3 H C2Hs H
/ /
(B)
. '/ C=C and
'\
C=C
"
Cl ' H H/ Br

Cl H C2Hs H
/ /
(C)
"/ C=C and "/ " c=c
H ' CH 3 Br H

H Cl C2Hs H
(D) / /
' C=C and " " c=c
H
/
' CH,
/
Br H
 -4-
6. Terylene can be produced from hem 9 refers to the followingiufonnation.
ethane l, 2- diol (HO - CH, -CH, - OH) and
benzene I, 4 dicarboxylic acid Etheue is normally susceptible to electrophilic
attack, but it is made attractive to nucleophiles
(HOOC -@--coOR). by complexing it with Pd2+ catalyst in the
Wacker process:
Which ofthe following characteristics would
terylene MOST likely possess?

(A) It has the same empirical formula as

its monomers.
(B) One of its monomers contains the
C = C functional group. 9. Which of the following options characterize
(C) It is the only product obtained when this mechanism?
its monomers react.
(P)/ . It can be hydrolysed by aqueous I. The CH2 : CH 2 complex decreases
sodium hydroxide. Pd 1

electron density in the double bond.

7. Which ofthe following statements does NOT
describe a nucleophile? ll. The 7t electrons of ethene occupy
vacant orbitals in Pd".
(A( Lewis acid III. The 7t electrons are no longer
(B) Lewis base available and their removal makes
(C) Species with a lone pair ethene positively charged.
(D) Reagent which attacks electron
deficient sites in molecules (A) land II only
(B) I and III only
(C) II and Ill only
8. The equation for the formation of the !PY I, II and III
anaesthetic, CF,CHBrCI, is

CF,CH,CI Br2 ) CF,CHBrCI. 10. Which of the following compounds is both an

alkene and an ester?

The type of reaction occuring is

(A)
(A) free radical substitution
(B) electrophilic substitution
( C) nucleophilic substitution H 0 H
(D) nucleophilic addition ....... q /
C-0-CH -CH=C
2 '
CH3

0 H
(C) ~ /
C-CH 2 -CH=C
H,,. 'cu 3

(D) ,,.CH2
CH -0-CH -C
3 2 '
ce,
 -5-
11. The complete reaction of phenol with aqueous 13. Whiph two products are formed in
bromine is characterised by a approximately equal amounts when
methylbenzene is treated with a mixture of
(A) white precipitate, a brown solution concentrated HNO, and concentrated
and an antiseptic smell H,SO,?
(B) brown precipitate, a colourless
solution and a sweet smell CH CH 3
.
~
(A)
~, white precipitate, a colourless solution 6 N Q2 and
and an antiseptic smell
N02
(D) brown precipitate, a brown solution
and a sweet smell
CH 3
~3
/
)DY iN02 and
12. When propanone reacts with hydrogen
cyanide, the formula of the product is N02

H
CH 3
~3
I (C)
(A) CH3.-C-CH3
I
0-CN
l N02
and

N02

(B) CH,-C-CH2-CN
II CH 3 CH 3

~
0 (D)

H N02
and
N02
h
I
(C) CH3 -C-CH2 CN
I Item 14 refers to the compounds P, Q, R
OH and S, whose structures are given below.
CN
P: CH,(CH,),CH 20H
I
Q: CH,(CH2},CH,COOH
?5 CH3 -C-CH3
I
0-H
. R:
S:
CH,(CH2 ) 3CHC1COOH
HO

14.

The corre~t sequence of the compounds
above in order of DECREASING acid
strength is
/
(A') R, Q, S, p
(B) Q, R, S, p
(C) P,S,Q,R
(D) s, R,Q, p
 -6-

Item 15 refers to the following structure of 18. Which ofthe following graphs illustrates the
tyrosine. titration of dilute suphuric acid wjth potassium
hydroxide solution?
co,e
14~
I (A)
e N-c-e pH
I
7

~ VolofH 2sq

OB (B)
pH 14LC_
7

15. The pH of tyrosine is MOST likely

VolofH 2sq
(A)
(B)
(C)
(D)
2.1
S.6
7.0
9.0
(C) pH
14l=
7

VolofH 2sq

16. Which of the following pieces of apparatus

possesses the HIGHEST degree of
uncertainty in measurement?
pH 14L(.
7

SJr( Beaker VolofH 2sq

(B) Burette
(C) Pipette
(D) Measuringcylinder 19. Solution A, 10. cm' of H,so,, is placed in
100 ml volumetric flask and made up to the
mark with distilled water. 25 cm' of this
17. Which of the following is NOT a property of solution is used to completely neutralise
a primary standard? 20.05 cm' ofO.O I mol cbn" solution ofNaOH.
What is the concentration of solution A?
% Low relativt molecular mass
(B) Very soluble in water ~ 1.0 x I 0"' mo! dm'
(C) Obtainable in a pure state (B) 2.0 x 10.. mol dm"'
(D) Does not undergo hydrolysis (C) 4.0 x 10.. mol dm"
(0) 4.0 x 10-2 mol cbn'

. ';
 -7-
20. Which of the following statements about Item 22 refers to the graph below which
gravimetric analysis is NOT true? shows the absorption calibration curve for Xn+
in the solution.
(A) Gravimetric analysis is a purely
quantitative method. j0.40
Gravimetric analysis never involves
the removal of volatile components
ofasolid.
J 0.30

(C) The analyte can be identified after

<
0.20
precipitation and isolation have
occurred. 0.10
(D) The amount of analyte lost due to
solvation is assumed to be
negligible. 2 4 6 8
[Xn+l in ppm

21. In an electronic transition in the UV/visible 22. What is the concentration in mol dm' of an
region of the spectrum, a wavelength of unknown solution of x+(aq) which has an
450 nm is absorbed. absorbance value of 0.20?

Planck constant (b) = 6.63 x 1034 J s (Atomic mass of X = 172 g mot')

Velocity oflight (c) = 3.00 x 10' ms'

The energy of the corresponding photon (in {( 2.91x10_, mol dm'

2.91 x Jo mo! dm'
Joules) is (C) 5.00 x 103 mo! dm'
(D) 8.61x101 mol dnr'
66.3 x 103 x 3 x 10'
(A)
4.50 x 10'
23. Hexane will not absorb light in the UV/visible
region of the spectrum because there is a
4.50 x 107
(B)
6.63 x 1034 x 3 x 108 large difference in energy between
the bonding and antibonding
orbitals
(C) (B) large difference in energy between
the bonding and non-bonding
orbitals
(C) small difference in energy between
6.63 x 1034 x 3 x 108
the bonding and non-bonding
4.50 x10 7 -
orbitals
(D) small difference in energy between
the bonding and antibonding
orbitals
 -8-
'
24. Whichofthe following pairs do NOT absorb 26. Which of the following spectra shows a
infrared radiation? possible fragmentation pattern of CH,Cl,?

I. H,O and HI [Isotopes present: "C, 'H, "Cl, l7Cl]

II. H, and c~
Ill.
IV.
NH, and HBr
CH4 and Br, (A)
.

(A) I and III
."
.. "C

:ti "
.; i
(B) I and IV i:ill
(C) II and III
jJJt II and IV
83 85 87
m/e
25. An unknown organic compound of molecular
mass of 44 g is analysed using infrared. The (B)
bonds 111"1! found at 1700 cm and 2800 cm.

The compound is MOST likely

(A) ethanol
(B) ethanoic acid
83 85 87
(CJ ethanal m/e
(D) carbon dioxide
(C)

83 85 87
m/e

83 85 87
m/e
 -9-

Item 27 refers to the following information. 29. Which of the following is NOT a visualising
agent in chromatography?
Sample X is a mixture of substances. X was
separated into its components using paper (A) Iodine
chromatography simultaneously with (B) Cellulose
individual samples of e, f, g and h. The (C) Ultraviolet light
chromatograph produced is shown below. (D )_ Ninhydrin

30. Which of the following statements about

partition coefficient may be true?

I. It does not vary with temperature.

II. The solute has to be in the same
molecular state in both solvents for
it to be a constant.
III. The two solutions have to be
concentrated for it to be a
constant.
SampleX e f g h
(A) I only
CB) II only
(C) I and II only
2 7. Which substances are MOST likely present (D) I, II and III
inSampleX?

(,K) e, f, g 31. Along with silicon dioxide, which of the

(B) e, f, h following compounds constitutes the main
(C) e, g, h impurities of bauxite?
(D) e, f, g, h
(A) Iron(II) oxide
~ Iron(III) oxide
28. A student is asked to determine the value of (C) Carbon dioxide
'n' in the hydrated salt, M2 S04 .nH20. The (D) Carbon monoxide
masses of M 2SO4 anll water of crystallization
in the salt are 5.65 g and 2.65 g respectively.
(Assume A, of M = 86] 32. Jn the fractional distillation of crude oil, the
different fractions are separated based on
The value of 'n' is MOST likely their

(A) 2 (A) solubility

(B) 3
(C) 5
'/ viscosity
{C) volatility
(DJ 7 (D) polarity
!

-JO-
33. In the Bosch-Haber process, N2 and H2 can 36. Compounds of sulphur suQh as sulphites are
be obtained from X and Y respectively. Which used as food additives. This is ~cause they
of the following pairs BEST describes these
sources? (A) he Ip to preserve the food by
dehydration
inhibit the oxidation of unsaturated
x y
fats
Ammonium (C) help to enhance the colour offood
(A)
salts Naphtha (0) improve the flavour of food
Ammonium
(B) Air
salts
(C) Air Naphtha 37. Which of the following plastics are
biodegradable?
Ammonium
(0) Air
salts (A) Polythene terephthalate
(B) Low density polyethene
34. For the m'anufacture of which TWO of the
fu llowing industrial products is chlorine most
n
(0)
Poly (3 - hydroxybutanoic acid)
Polyvinylchloride
widely used?

I. Solvents 38. Which of the following are produced when a

II. Sodium chloride hydrocarbon undergoes complete combustion?
III. Polyvinylchloride
IV. Chlorofluorocarbons I. Water
II. Carbon monoxide
(A) I and II III. Carbon dioxide
JB) land III IV. Oxygen
(C) II and III
(0) Hand IV (A) I and II only
,ear I and m only
(C) II and ill only
35. In the production of sulphuric acid by the (0) ID and IV only
Contact process the following exothermic
reaction takes place:
. 39. Which ofthe following are greenhouse gasa?
2SO,(g) + O,(g) V20 5 ,420"C, 2atm , 2SO,(g)
I. Nitrogen
Which of the following conditions would II. Carbon moooxide
favour the forward reaction? III. Carbon dioxide
IV. Methane
I. Low pressure v. Sulphur dioxide
II. Excess oxygen
III. U>w temperature (A) II and III only
J.i) III and IV ol)ly
(A) I only (C) Ill and V only
I and II only I, II and IV only
~(
(0)
II and III only
(0) I, II and III
 - 11 -
Item 40 refers to the schematic diagram 43. Chlorine radicals are formed in preference
below. to fluorine radicals when chlorofluorocarbons
are impacted by ultraviolet radiation. This
Nitro en Rain and occurs in the upper atmosphere because
fixation N2 lightning
Denitrifying
x the bond enthalpy of the C - Cl bond

w
bacteria

Deca
f.""-
Organic
N,
bacteria

4
Plants
1
~
(B)
(340 kJ mol- 1) is less than that of
theC- F bond (484 kJ mol- 1)
the bond enthalpy ofthe C- Cl bond
corresponds to the energy of the
ultraviolet radiation
compounds (C) the chlorine radical is more reactive

Bacteria z Bacteria J (D)

than the fluorine radical
the fluorine radical is more reactive
than the chlorine radical

40. W would MOST likely be

44. The primary chemical pollutants involved in
(A) nitrates the formation of photochemical smog are
(B) nitrites
fP'} NH 3 and ammonium salts (A) carbon monoxide and nitrogen
(D) nitric(V) acid dioxide
(B) carbon monoxide and nitrogen
monoxide
41. Eutrophication results in too much algal hydrocarbons and nitrogen monoxide
growth in rivers or ponds, due to fertilizer hydrocarbons and nitrogen dioxide
run-off.

Which of the following pairs is responsible 45. Sulphur dioxide gas, produced when coal is
for this growth? used as a fuel, can be BEST removed from
the waste gas stream by
(A) Nitrates and ammonia
(B) Phosphates and sulphates (A) water
,(C) Sulphates and carbonates (B) sodium sulphate
(D) Phosphates and nitrates (C) sodium carbonate
(9) calcium carbonate

42. Ozone in the troposphere has NOT been

linked to

(A) dying forests

(B) greenhouse effect
(C) asthma attacks
}13-) bleaching of coral reefs

IF YOU FINISH BEFORE TIME IS CALLED, CHECK YOUR WORK ON TIDS TEST.

nn 1.,ni n/r A Pt: ')MR