Chemistry U2 P1s Answers

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TESTCODE02212010
FORMTP2008168 MA Y/JUNE2008
Rest of Region
CARIBBEAN EXAMINATIONS COUNCIL
ADVANCED
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
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,
y.< C2H,-C-OH
I
CH3
H H H H H H H H
.I I I I I I I I
(C) 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 monomer.
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 complex decreases
CH2 : CH 2
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
,,.CH2
(D)
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

CH CH 3
solution and a sweet smell
white precipitate, a colourless solution .

(A)
6 N Q2 and
and an antiseptic smell

N02
(D) brown precipitate, a brown solution
and a sweet smell
/
CH 3
)DY
©iN02 and
12. When propanone reacts with hydrogen
cyanide, the formula of the product is N02
I CH 3
©l
(C)
(A) CH3.-C-CH3 and
I
0-CN N02
N02
(B) CH,-C-CH2-CN
II CH 3 CH 3
0
h
(D)
and
H N02 N02
(C) CH3 -C-CH2 CN
I Item ·14 refers to the compounds P, Q, R
OH and S, whose structures are given below.
CN
I P: CH,(CH,),CH 20H
?5
Q: CH,(CH2},CH,COOH
CH3 -C-CH3
I
. R: CH,(CH2 ) 3CHC1COOH
0-H S: HO
14. The
©
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
e N-c-e (A)
pH
• I
7
14LC_
VolofH 2sq
OB (B)
pH
15. The pH of tyrosine is MOST likely
14l=
VolofH 2sq
(A) 2.1
(C) pH
(B) S.6
(C) 7.0 7
(D) 9.0
14L(··.
VolofH 2sq
16. Which of the following pieces of apparatus

pH
possesses the HIGHEST degree of
uncertainty in measurement? 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?
%
(B)
Low relativt molecular mass
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 10·34 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 10·3 mo! dm'
66.3 x 10·3• x 3 x 10'

(D) 8.61x10·1 mol dnr'
(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 10·7
(B)
6.63 x 10·34 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 10·34 x 3 x 108
4.50 x10· 7 -
the bonding and non-bonding
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]
H, and
.
II.
Ill. NH, and HBr
IV. 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. Ninhydrin
(D )_
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 Carbon monoxide
masses of M 2SO4 anll water of crystallization

(D)
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)
(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 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
37. Which of the following plastics are

(C) Air Naphtha
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 (0) I, II and IV only
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
x the bond enthalpy of the C - Cl bond
f.""-
Denitrifying
1
bacteria (340 kJ mol- 1) is less than that of
bacteria theC- F bond (484 kJ mol- 1)
(B) the bond enthalpy ofthe C- Cl bond

Organic corresponds to the energy of the
w Deca
N, 4
Plants
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

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. . . .
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FORM TP20081 68 MAY/JUNE200 8
Trinidad
CARIBBEA N EXAMINA TIONS COUNCIL
ADVANCEDPROFICIENCYEXAMINATION
CHEMISTRY - UNIT2
l PaperOl
90minutes
( 15JULY2008(a.m.) )
READ THE FOLLOWING INSTRUCTIO NS CAREFULLY .
1. This test consists of 45 items. You will have 90 minutes to answer them.
2. In addition to this test booklet, you should have an answer sheet.
3. Do not be concerned that the answer sheet provides spaces for more answers than there are items in this
test.
4. Each item in this test has four suggested answers lettered{A), (B), {q, (D). Read each item you are about
to answer and decide which choice is best.
5. 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.
Sample Item
Whichofthefoll owingistheHIG HESTenergytra nsitioninanorga niccompound?
(A) n to a* Sample Answer
(B) n to 1t*
(C) cr to 0'*
(D) 1t to 1t*
The best answer to this item is "a to cr*", so answer space (C) has been shaded.
6. Ifyou want to change your answer, erase it completely and fill in your new choice.
7. Whenyouareto ld to twn the page and work as quickly and as carefully as you can. Ifyou cannot
answeranitem,o mititandgoonto thenextone. Yourscorewillb ethetotalnumbe rofcorrectansw ers.
10. The use ofnon-progranu nable calculators is allowed.
DO NOT TURN TffiS PAGE UNTIL YOU ARE TOLD TO DO SO.
Copyright© 2008 Caribbean Examinations Council.

All rights reserved.
22212010/CAPE 2008
• AFFLXSEALHERE •
-2-
1. Which of the following is true for butanoic 3. The compound which shows both cis-trans
acid? isomerism and optical isomerism is
Molecular Empirical H H
formula formula
CH20
(A) "c c
/
/
H
"'
(A) C4Hs02 /
(B) C4H602 CH20 c C-C-H

(C) C4Ha02 C2 H4 0 /
(D) C 4H 8 0 C 2 H 40 H
/I" H
H
H
" " Br H
2. A hydrocarbon contains 87.8% carbon and
12.2o/o hydrogen by mass. Its empirical Cl Cl
fonnulais
CH "c
/
c
/
"'
(A)
(B)
(B) CH 2 c C-H
(C)
(D)
C2H3
CJHs H
/I"- H
H
H
/
"' Cl
H H
' c c
/
"
(C) /
C-H
c
H
/I
Br
'H H
" H
H H
"/ c c
/
(D)
c ' C-H
H /I' H
H
H
/
' H
GOONTOTHENEXTPAGE
222120 l O/CAPE2008
-3-
4. The carbonyl group is NOT present in 6. Which ofthe following alcohols will NOT be
oxidised by acidified potassium chromate
(A) aldehydes (VI)?

(B) ketones
alcohols
(C) (A)
(D) carboxylic acids
5. Which statement is true about C - C bonds? CH 20H
(A) A double bond is made of a sigma (B)

I
CH - C - H
bond and a pi bond.

3 I
(B) There is a higher electron density
between the atoms in a single bond OH
than in a double bond.
(C) The distance between the nuclei of H

the carbon atoms is shorter in single
I
bonds than in double bonds. (C)
(D) Single bonds are more reactive

CH -CH - C -OH
3 2 I
towards most reagents than double

bonds. CH 3
CH 3
I
CH- C - OH
(D)
3 I
CH 3
7. Which of the following compounds is
hydrolysed by water?
(A) C2H 50H
(B) C6H 5COOH
(C) C 6H 5CH2 Cl
(D) 0 Cl
GOONTOTHENEXTPAGE
2221201 O/CAPE2008
-4-
8. Ethanol can be formed by the following 11. At which ofthe carbon atoms in the molecule
reaction: below is electrophilic attack MOST likely?
"c / (D)
The mechanism used is
(A)
(B)
electrophilic addition
electrophilic substitution
nucleophilic addition
A\CH Br 2
(C) (C) \
(D) nucleophilic substitution
""--.....
..____(A)
9. Hydrogen cyanide adds to ethanal but not to (B)
ethene because
(A) ethanal is more susceptible to A compound gives a white precipitate when
electrophilic attack than ethene

12.
shaken with aqueous bromine. The
(B) the addition product formed with compound could be
ethene would be unstable

(C) ethanal is more susceptible to C2H4
nucleophilic attack than ethene

(A)
(B) C2H 5COOH
(D) ethanal is more susceptible to free C6H 50H

(C)
radical attack than ethene (D) C2H 50H
CH 3
10. can react to

Methylbenze ne, 13. Which ofthe following would release a proton
MOST readily?
(A)
(B) C}\COOH
produce (C) C6H 50H
(D) Cf\OH
Cl
A possible use for the product formed by the

14.
Which reagent and conditions are MOST polymerisati on ofpropene, C 3H 6, is as a
suitable for the reaction?

(A) fuel
(A) Chlorine with u.v. light (B) liquid
(B) Chlorine in the dark (C) disinfectant
(C) Chlorine withAICI3 (D) plastic material

(D) Concentrate d HCl heated under
reflux
GOONTOTHENEXTPAGE
22212010/CAPE2008
-5-
15. Which of the following represents the 17. Which of the following will NOT affect the
repeating unit obtained from the addition accuracy ofthe results in a titrimetric analysis?
polymerisation ofthe monomer,
CHCl=CHC l? (A) Purity ofreagents
(B) Blowing the reagent out ofthe pipette
(A) H H H H tip
I (C) Overshooting the calibration mark of
I I I
-C-C- c- C- the volumetric flask
I I I (D) Adding excess water to the conical

I flask
Cl Cl Cl Cl
What is the concentratio n (mol dm- ) in an

3
18.
(B) Cl H aqueous solution that contains 63.3g of
I I in 1.0 dm3 of solution? [The
-C-C- relative formula mass is 3292.]
I I (A) 1.92x IO·' M

Cl H
(B) 2.95 X 104 M

(C) 3.11 x 10·3 M
5.77x 10· 1 M
(D)
(C) H H
I I
-C-C- Items 19-20 refer to the following information.
I I
Cl Cl A student carries out the gravimetli.c analysis

ofa soil sample taken from an area surrounding
a garage. The soil sample is found to be
(D) Cl H Cl H contaminate d with Pb2+ ions. 100 cm3 of a
I I solution obtained from the sample when mixed

I I
-c-· c - C - C- with 25 cm3 of 0.100 mol dm·3 HCl yields
0.010 g oflead chloride. [The relative formula

I I I I
Cl H Cl H mass oflead chloride is 278.2.]
19. The balanced equation for the reaction
between lead ions and hydrochloric acid is
Item 16 refers to the following burette readings: (A) Pb (s) + 2HC1 (aq) PbC12 (s) +
H2(g)
25.1, 25.2, 24.9, 24.8

(B) 2Pb (s)+2HCI (aq) (s)+
16. The standard deviation ofthe readings is (C) Pb2+(aq)+ 2HC1 (aq) PbCl2 (s) +
2H+(aq)
(A) 0.245
(D) Pb2+(aq) + 2HC1 (aq) PbCI2 (aq)
(B) 0.183 +2H+(aq)

(C) 0.122
(D) 0.033
20. What is the concentratio n of Pb2+ in the
original solution?
(A) 3.60 X 10·5 mol dm·3
(B) 3.60 x 104 mol dm·3

(C) 5.40 x 104 mol clm·3
(D) 7.20 x 104 mol dm·3
GOONTOTHENEXTPAGE
222120 10/CAPE2008
-6-
Item 21 refers to the following regions ofthe 25. In which ofthe following processes is infra-
electromagnetic spectrum. red spectroscopy MOST likely used?
I. Visible light I. Monitoring atmospheric pollution
II. X-ray II. Breath-alcohol analysis
III. Infrared III. Quantitative analysis
IV. Ultraviolet
(A) I only
21. Which ofthe following is the correct order (B) II only
for increasing wavelength? (C) I and II only
(D) I and III only
(A) II, III, I, IV

(B) II, IV, I, III
(C) II, IV, III, I Item 26 refers to the mass spectrograph below.
(D) IV, II, I, III
22. Which two features BEST describe ultraviolet

Q)
u
c: I
radiation?
10
'"0
c:
::J
..0
-
10
(A) Short wavelength and high frequency
<1J
0')
(B) Long wavelength and high energy ta
(C) Short wavelength and low energy

c:
<1J
(D) Long wavelength and low frequency Q)

m
0..
m/e values
23. Which of the following types of electronic
transition would NOT produce absorption in
the UV/VIS region ofthe spectrum? 26. Which ofthe following correctly identifies I,
II and III above?
(A) 1t--)> 1t*
(B) n 1t* Base Molecular M+1
(C) 0' 1t* peak ion

(D)
(A) I II lll
(B) II I III
Item 24 refers to the diagram below which (C) II III I
represents the structure of a water molecule. (D) III II I
24. Which of the following would be exhibited
by the molecule?
(A) Bending and stretching vibrations
(B) Asymmetrical stretching vibrations
(C) Bending vibrations

(D) Symmetrical stretching vibrations
GOONTOTHE NEXTPAGE
2221201 O/CAPE2008
-7-
27. Which of the following statements reflect the advantages ofthin-layer chromatogra phy over paper
chromatography?
I. Thin-layer chromatogra phy is slower than paper chromatograp hy.
II. Thin-layer chromatogra phy may be made from different solids, thus a wide variety of mixtures
can be separated by careful choice.
III. Thin-layer chromatograp hy can be used for quickly selecting the best conditions for larger-scale
phases.
(A) I and II only
(B) land ill only
(C) II and III only

(D) I, IT and III
Item 28 refers to the following chromatogra m which is obtained when a 1 : 1: 1 : 1 of ethanol,
propan-1-ol, butan-1-ol and hexan-1-ol is analysed by gas-liquid chromatography.
n
III
IV I Ethanol
II Propan -1- ol
III Butan -1- ol
IVHexan -1-ol
5 10
0
Retention time (min)
28. Which compound is present in the highest concentration ?
(A) Ethanol
(B) Hexan -1- ol
(C) Propan- 1 - ol
(D) Butan- 1 - ol ·
GOONTOTHENEXTPAGE
2221201 O/CAPE2008
- 8-
Item 29 refers to the following boiling point composition curves for three mixtures.
I II III
29. Which of the following CANNOT be completely separated by fra,:tional distillation?
(A) Ionly
(B) Ilonly
(C) I and II only

(D) II and Ill only
30. A solution of 10 g of a carboxyli c acid (weak

32. In the electrolys is of molten alumina, Al20 3,
the reaction at the cathode is BEST
acid) in 100 cm3 of water is shaken with 100

represent ed by
cm3 of ethoxyet hane. It is found that only

6.5 g ofthe acid remains in aqueous solution
at equilibriu m. The partition coefficien t is

(A) AP+(l) + 3e· (l)
AP+ (1) + 2e· (s)
(B)
AI+(s)
(C) AP+ (aq) + 2e·
(A) 0.054
(D) 2AP+ (l) + 6e· Al 2 (g)
(B) 0.54
5.4
(C)
(D) 54
Item 33 refers to the following fractions of
crude oil
31. Which ofthe following are importan t factors
to consider in determin ing the location of a

I. Diesel
II. Petrol
factory?
Refmery gas
III.
IV. Kerosene
I. Proximity to a potential workforc e
II. Availab ility to a means of
33. The correct order in terms of increasi ng

transportation -
boiling point is
III. Potential pollution of air, land and

water
(A) I, II, III, IV

rv. Proximity to raw materials
III, l, II, IV
(B)
(C) III, II, I, IV
(A) I, II and III only

(D) lll, II, IV, I
(B) I, II and IV only

(C) r, III and IV only
(D) £, II, III and IV
GOONTOTHENEXTPAGE
222120 l O/CAPE2008
-9-
34. In the Haber Process, a maximum yield of 38. In the Contact Process, why is sulphur trioxide
NOT directly dissolved in water to produce

ammonia can be achieved by decreasing
concentrated sulphuric acid?
(A) temperatur e
(B) catalyst (A) It is insoluble in water.
(B) The reaction is highly exothermic.

(C) pressure
(D) particle size (C) It is extremely toxic.
(D) It is colourless and odourless.
35. During fermentati on to produce ethanol,
which ofthe following is NOT used to break 39. There are four reactions that take place during
down glucose? the Contact Process. The first two reactions
are represented as follows:

(A) Water
Energy s (s) + 02 (g) -4 so2 (g)

(B)
(C) Oxygen 2S02 (g) + 0 2 (g) S0 3 (g)
(D) Enzymes
Which of the following are the other two
reactions?
36. Which ofthe following are consequen ces of
the consumption ofalcohol? I. S03 (g) + H 2S04 H 2 S 20 7 (1)
II. H 20 (I)+ S03 (g) H 2S04 (aq)

I. Stimulates the central nervous system Ill. H2 S2 0 7 (1) + H 2 0 {1) 2H2 S04 (1)
II. May cause liver disease IV. HzO (1) + 802 RzS0 3 (aq)
III. Reduces manual dexterity
(A) I and II only

(A) land II only (B) I and III only
(B) I and III only (C) II and IV only
(C) II and III only (D) III and IV only
(D) I, II and III
40. The major reservoir for the water cycle is
37. In the electrolys is of brine using the

diaphragm cell, two by-produc ts of this
process are
(A) oceans
(B) glacial ice
(C) freshwater bodies
(A) hydrogen and sodium hydroxide

(D) atmospheri c water vapour
(B) chlorine and sodium
(C) mercury and hydrogen
(D) chlorine and oxygen

41. The presence of phosphate ions (POt) can
be detected using
(A) ammonium molybdate

(B) sodium thiosulphate
(C) potassium thiocyanate solution
(D) potassium hexacyan oferrate(I I)
solution
GOONTOTHENEXTPAGE
222120 1O/CAPE2008
- 10-
42. The ozone layer found high in the stratosphere 44. Nitrogen monoxide, NO, is responsible for the
destruction ofozone in the stratosphere. How
(A) is toxic to plants can N 0 be generated in the atmosphere?
(B) reacts with atmospheric pollutants to
form smog I. Combustion of fossil fuels
(C) protects against the sun's harmful II. Lightning discharge

UVrays III. Reduction ofN02 by S02, both of
which are present in the atmosphere

(D) is an environmen tal hazard as it
readily disintegrates fabric and
rubber (A) I and II only
(B) I and III only

(C) II and III only
43. Which of the following may be a result of (D) I, II and III
light-induced reaction ofpollutants in the air?
I. Global wanning 45. Which of the following is a disadvantage of
II. Photochemical smog recycling plastic?
III. Greenhouse effect
(A) Decreased masses are sentto landfill.

(A) I only (B) Plastics are generally of low
biodegradability.
(B) II only
(C) I and III only (C) More toxic fumes are released
(D) I, II and III relative to incineration.

(D) Recycling minimises wastage of
materials.
IF YOU FINISH BEFORE TIME IS CALLED, CHECK YOUR WORK ON TillS TEST.
2221201 O/CAPE2008

.,.,.,/
TESTCODE02212010
FORMTP 2009158 1vfAY/JUNE2009
CARIBBE AN EXAMINA TIONS COUNCIL
ADVANCED PROFICIENC YExAM1:NA TION
CHEMISTRY - UNIT 2
PaperOl
.
90minutes
(o9 JUNE 2009 (p.m.D
READ TBE FOLLOWING INSTRUCTIONS CAREFULLY .
1. This test consists of45 items. You will have 90minutesto answerthem.
. 2. In addition to this test booklet, you should have an answer sheet.
3. Do notl;>e concerned that the answer sheetprovides spaces formore answers than there are items
in this test.
4. Eachiteminthis te:Stbasfoursu ggestedanswer slettered(A),(B );(C),{D). Readeachitem you

are about to answer and decide which choice is best. ·
5. On your answer sheet, find thenumberwhic hcorrespondsto your item andsb.aciethe spacehavmg
the same letter as the answer you chosen. Look at the sample item below.
Sample Item
Wbichofthe following is the HIGHEST energy transition in an organic compound?
Sa.mpleAnswer
(A) n to cr*
(B) n to 1t*
(C) cr to cr* @®G@
(D) 1t to 1t*
The best answer to this item is "cr to cr*", s6 answer space (C) has been shaded.
6. Ifyou want to change your answer erase it completely before you fill in your new choice.
7. When you are told to begin, turn the page and work as quickly and as carefully as you can. Ifyou
cannot answer an item, omit it and go on to the next one. Your score will be the total number of
correct answers.
8. You may do any rough work in this booklet
.I
--
·-
-
9.
10.
Figures_ are not necessarily dra\ltn to scale.
The use ofnon-program mable calculators is allowed.
-=
i iiiiii
DO NOT TURN THIS PAGE UNTIL YOU ARE TOLD TO DO SO.
- Copyright© 2009 Carib beanExarninatio ns Council.

-
" """'"Z'
All rights reserved.
iii.iii 0221201 O/CAPE2009
-.2-
1. Volatility of organic compo11nds depends on 5. A motorist suspects that his gasoline is
the strength of the intennolec ular forces contaminated \vith ethanol. Which reagent
can the motorist use to detect the presence
present Which compound below would be

of ethanol?
the MOST volatile?
(A) (A) Br2 (aq)

(B)
(B)
(C) NaOH (aq)
(C)
(D)
(D) KMnO 4 (acidified)
In the reaction between the ethene and

2. Combustio n analysis ofO.l S g of an organic 6.
bromine, which statements about the reaction

compound produces 0396 gofcarbon dioxide
and0.216 gofwater. The empirical formula

mechanism. may be true?
of the compound, given tb.S.t it contains

L A carbocatio n forms in the rate
carboil, hydrogen and oxygen only, is
detmnining step.
IT. A dative covalent bond forms

(A) C 3H 8 0
between the ion and the
(B) C4H 1 0
carbocati.on.
(C) C 2H 1 0 4
(D)
m. Heterolytic fission of bromine-
bromine bond occurs.
(A) Ionly
3. The couect IUPAC name for the structural (B) I and ll only
formwa (C) !Iandillon ly
(D) I, II and ill

H CH3 CH3
I I I
H-C-CC H2CHCH3 is
I I 7. Which ofthe following does NOT descnbe a

H CH3 nucleophile?
(A) 2, 4-trimethyl pentane
(B) 2, 2, 4-trim.ethyl octane (A) Lewis acid

(B) Lewis base
(C) 2, 4, 4-trimethyl pentane

(C) Species with a lone pair
(D) 2, 4, 4-trimetbyl octane
(D) Reagent which attacks electron

deficient sites in molecules. ·
4. Which of the following compounds show

optical activity?
I. COOH
II. HOCH = CHOH .

m. (CI)
N. HC(Br)IC l .
(A) I and II only
(B) I and N only
(C) ll and m only

(D) .illandlVo nly.
GO ON TO THE NEXT PAGE
. 02212010/CAPE2009
-3-
8. 2-hydroxy- 2 - methylpropan oic acid can be formed from in two steps, illustrated below.
CH3
I Step Y ).
CH3 -C-C:::N
I
OH
Which of the following statements about these steps may be true?
I. Step X involves nucleophilic addition.
IT. Aqueous potassium cyanide is the reagent in Step X.
ill. Step Y involves hydrolysis.
(A) Ionly
(B) I and II only

(C) ITandillonly
(D) I, II and m
Item 9 refers to the following reaction. Item 10 refers to the following reaction.
Reagent
>
Br
10. The product of the following reaction is

9. The reagent in the above reaction is formed by
(A) Br2 I sunlight (A) free radical substitution
(B) Br2 I FeBr3 (B) mtCleophilic substitution

(C) Concentrated I cone. HN0 3 (C) an elimination reaction
(D) Concentrated HCl/ Sn (I)) electrophilic substitution
11. Which of the following compounds is the strongest acid?
GO ONTO THE NEXT PAGE
02212010/CA PE2009
-.4-
e inducti ve and negative

12. \Vbich ofthe following options is correct for the conjugative, positiv
inducti ve effect, shown by the structures below?
OH
70
t
@
Q R
I
H - C--7- 0
(A) Negative inductive Positive inducti ve Conjug ative

effect ·
effect effect
(B) Conjugative Negati ve inducti ve Positive induct:i:ve --
effect effect effect
Conjug ative Positive inductive

I
(C) Negati ve :inductive
Negati ve inductive
Positive inductive Conjugative
(D)·
effect effect
effect
14. The repeating unit obtained from the addi:tion

13. 'Which of the follow ing is NOT 1rue about
condensation polymerisation? polymerisation ofthe
CHCl = CHCl is
(A) Themo lecular mas8 ofthep olyme r

H H H H
is a multiple oftb.e combined. masses
ofits monomers. I I I I
(B) The polym er can be hydrol ysed to (A) - c- c - c - c -

form its monome.r:s. I I I I
(C) The polym er has physic al and c1 a a a·
chemical properties that differ from

H . H
the monomer units.

I
(D) Small molecu les are elimin ated I
during the condensation process. (B) -e-e-
l I
Cl
CI
Cl H
I I
(C) -e-e-
l I
H
Cl
Cl H Cl H
I I I I
(D) - c - c - c - c-
1 I I I
Cl H Cl H
0221201 0/CAPE2009
-5-
15. ·Which ofthe following is true for glucose and starch?
Starch Glucose
(A) High solubility in water High solubility in water
(B) Low in water Low solubility in water
(C) Gives blue/black colour with iodine Gives blue/black colour with iodine
(D) No reaction with Fehling's solution Reduces Cu2+ in Fehling's solution
to red/brown Cu20
16. Which of the following pieces of apparatus 19. Which of the following statements about
possesses the HIGHEST degree of gravin;letric analysis is NOT 1rue?
uncertainty in measurement?
(A) analysis is a purely

(A) Burette quantitative method.
(B) Gravimetric analysis never involves

(B) Beaker
(q Pipette
(D) Measuring cylinder ofasolid. .

(C) The analyte can be identified after
precipitation and isolation have
17. Which ofthe following is NOT an instrument occurred.
used in titrimen-y? (D) The amount of analyte lost due to

solvation is assumed to be
(A) Barometer negligible.
(B) Thermometer
(C) Potentiometer
20. Treatment of a 10.00 g sample containing a
(D) Conductivitymeter
chloride salt with excess silver nitrate solution
produced 8.08 g ofSI1ver chloride.

18. The concentration of an ammonia solution is (Ag= 108, Cl=35.5)
determined by titrating 25.0 cm3 ag3.inst

The expression for the percentage of chloride
0.2 J?Ol dm-3 sulphuric acid to give an end

in the sample is
point of27.5 cm3 •
The concentration ofammonia ("mmol dm:l)

143.5x8.08 xlOO
(A)
is given by
35.5xl0.00
0.2x 27.5
(A) 35.5xl0.00 xlOO
25 (B)
143.5x8.08
0.2x27.5
(B) 35.5x 8.08 xlOO

2x25 (C)
143.5 X 10.00
2x0.2x27.5
(C) 143.5 X 10.QQ

25 (D) xlOO
35.5x 8.08
2x 0.2x 25
(D)
27.5
GO ON TO NEXT PAGE
02212010/CAPE2009
-?-
25. W'nich of the follow ing speci es is NOT a·
21. \Vhich ofthe followingutilizesvibrations?

significant fragment from 1he mass spect rum
(A) Radio wave of ethanol? ·
(B) Infrar ed
(C) UVN IS
(D) X-ray
22. The struc tural feature·s whic h caus e

absor ption in the UVN IS regio n of the
spect rum are know n as 26. In them_ass spect rome ter a molecular ion is
formed from a by
(A) crbonds
(B) chromoph(!res (A) "loss of a proto n

(B) gain electron
(C) isolated 1t bonds

(C) loss of an electron
(D)- lone pairs of electrons

(D) fragmentation ofthe compound
23. The ion [FeSC N)2+ has a mola r

1 27. Which oftbe following is NOT a visualising
absorptivity (E) of7.0 x 10 (im3 mol- cm- •
3 1
agent in chrO'matography?
.The concentration ofits solution, which gives

Iocline.
an abso:Fbance of 4.2 when meas ured in a (A)

(B) Cellulose
(C) N"mhydrin
(A) 3 X 1o-J mol dm-3 (D) t.ntraviolet light
6 x 1Q-3 mol dm.-3

(B)
(C) 3 x 10-4mol dm-3
(D) 6 x 10-" mol dm"3 . 28. Which ofthe following is LEAST commonly
used as a statio nary phas e in chrom a-
tography?
24. In an IR spec trum , an abso rptio n at
3400 cm-1 corre spond s to an -OH group in (A) Starc h

a .molecule. (lJ.L m = (B) Alum ina
(C) Silie;a gel
The wave lengt h corresponding to this (D) Cellulose

absorption is
(A) 0.294 p.m

29. Which of the following are advantages of
(B) 2.94 J.liD.
(C) 29.4 Jlill

steam disti11.a1ion?
(D) 294 J.llD I. It occurs unde r reduc ed press ure.
II. The components do not decompose.
ill. It provides savings in fuel cost.
(A) I and ll only-
(B) I and ill only .

(C) II and ill only
(D) I,ll and ill
GO ONT O THE NEXT PAG E
02212 010/C APE2 009
-7-:
30. Which of the followin g statemen ts about 33. 'Which of the followin g is represen ted by
partition coefficie nt may be true? c4

cl- hydrocar bons?
I. It does not vary with temperature. (A) Kerosine
II. The solute has to be in the same (B) Dieseloi1
molecular state in both solvents for (C) Gasoline

it to be a constant. (D) Re:finezy gas
m. The .·two solution s have to be
concent rated for it to be a
constant .
34. The nitrogen used in the manufac ture of
ammoni a by the Haber Process is obtained

(A) !only
(B) II only from
(C) I andll only

(D) I, II and ill (A) fertilizers
(B) the nitrogen cycle
(C) fractional dist:iJ.lation ofliquid air
31. Which ofthe followin g influenc e location of (D) fractional distillation of crude oil
an industrial plant?
I. Proximity to housing schemes 35. Which of followin g is NOT ne:essar y
n. Proximity to port for wine making?

m.
. IV. Good electricity supply (A) Yeast
(B) Oxygen
(A) Iandllo nly (C) Enzyme
.(B) !IandiD only (D) Carbohydrate
(C) II, ill and IV only
(D) I, II, m and IV

36. Which ofth.e followin g are conseque nces of
the consump tion ofalcohol?
32. Along With silicon dioxide, which of the

followin g compou nds constitut es the main I. Stimula tes the central nervous
system
impurities of bauxite?
IT. May cause liver disease
(A) Iron(II) oxide Reduces manual dexterity

(B) Iron(lli) oxide
(C) . Carbon dioxide (A) I and IT only
(D) Carbon monoxid e (B) I.andillo nly
(C) rr and ill only

(D) I, II and ill

0221201 0/CAPE 2009
- 8-
ine 40. The biolo gical oxyg en dem and (BOD)

of
Item 3 7 refers to the manufacture of chlor unt of oxyg en
by the elec troly sis of brin e usin g the wate r meas ures the amo
diaph ragm cell.

(A) pres ent in a fixed volu me ofwate r
(B) used by aqua tic orga nism s durin g

37. The anod e is mad e up of
respiration
(C) need ed by micr oorg anism s as they
(A) steel
deco mpo se orga nic matt er
(B) graphite
plati num with a coating of asbestos

(D) prod uced by aqua tic plan ts in
(C) photosynthesis
(D)· titan ium with an inert coati ng of
ruthe nium (IV) oxide
41. Whi ch follo wing ions are signi fican t
the contributors to eutrophication?

38. For the man ufac ture of whic h TWO of
ucts is chlo rine
follo wing indu stria l prod

I. PO/ -
Solventl
II. No;
I.
II. Sodi um chloride SOl -

Polyvinylchloride
m.
m.
rv. Cblorofl.uorocaxbons a-
IV.
(A) land II
(B) land ill

(A) Iand llon ly
Iand illon ly
(C) Tian dill

(B)
(C) I, nan d m only
(D) llan diV

(D) I, II, m and IV
39. "Which of the follo wing indu strie s use

42. A redu ction in the ozon e layer is believed
to
sulphuric acid?
have been caus ed by the actio n of
I. Fert:i1fzers (A) sulphur dioxide
II. Paint
(B) CFC s
m. Fibres
(C) meth ane
rv. Dete rgen ts
(D) carbo n dioxide
I, II and m only
{B) I, ill and IV only
(C) II, m and IV only
(D) I,II, illa ndN
GO ONT OTH ENE XTP AGE
0221 2010 /CAP E200 9
-9-
43. Which of the following statements on 44. Nitrogen monoxide, NO, is respoilSlble for the
environmental effects is true? · destruction of ozone in the stratosphere. How
can NO be generated in the atmosphere?
/ (A) Greehouse effect leads to global

Combustion offossil fuels
war.tniD.g. I.
(B) Global warmmg leads to greenhouse n. Lightning discharge
III. Reduction ofN0 2 by S0 2,, both of
(C) - Pbtotochemical smog leads to global which are present in the a1mosphere
warming.
(A) landllonly
(D) Eutrophication leads to greenhouse
effect. (B) - Iandllionly
(C) IIandillonly
(D) L IIandiD
45. Which of the following plastics are
biodegradable ?
(C) Poly (3 - hydroxybutanoic acid)

(D) Polyvinylchloride
lFYOUFINISHBEFORETIMEIS.CALLED,CHECKYOiJRWORKONTIDSTEST.
j'
0221201 O/CAPE2009
CAPE Chemistry 2010 U2 P1
1. Which of the following pairs of formulae is 4. The compound which shows both cis-trans
true for butanoic acid? isomerism and optical isomerism is
Molecular Empirical
(A)
Formula Formula
(A) C 4 H 8O 2 CH 2O
(B) C 4 H 6O 2 CH 2O
(C) C 4 H 8O 2 C 2 H 4O
(D) C 4 H 8O C 2 H 4O
2. Combustion analysis of 0.18g of an organic
compound produces 0.396g of carbon dioxide (B)
and 0.216g of water. The empirical formula of
the compound, given that it contains carbon,
hydrogen and oxygen only, is
(A) C 2 H 8O 4
(B) C 3 H 8O
(C) C 4 H 8O
(D) C6 H16O 2
(C)
3. When propane reacts with Cl2(g) in the
presence of sunlight, two possible mono-
substituted products, 1-chloropropane and
2-chloropropane are formed. What is the ratio
of 1-chloropropane to 2-chloropropane?
(A) 1:2
(B) 1:3
(C) 2:1
(D) 3:1 (D)
5. The formula, C6 H 5COOH, indicates that 9. Which of the following compounds will NOT
decolourize bromine water but will decolourize

(A) an acid group is present
potassium permanganate (VII) on warming?
(B) the compound is ketone

(A) Butane
(C) the compound is derived from hexane

(B) Ethanol
(D) seven carbon atoms are arranged in a (C) Ethene
chain (D) Ethanoic acid
6. In the reaction between ethene and bromine, 10. A compound, X, reacts with
which statements about the reaction
mechanism may be true? I 2,4-dinitrophenylhydrazine (DNPH) to
give an orange precipate

I. A carbocation forms in the rate
II Fehling’s solution to give a red

determining step.
precipitate
II. A dative covalent bond forms between III aqueous alkaline iodine to give yellow
the bromide ion and ethene. crystals
III. Heterolytic fission of the bromine-
bromine bond occurs. Compound X is most likely
(A) I only
(A)
(B) I and II only
(C) II and III only
(D) I, II and III
7. The equation for the formation of the
anaesthetic, CF3CHBrCl, is
(B)
CF3CH 2Cl Br2

→ CF3CHBrCl
The type of reaction occurring is
(A) electrophilic substitution
(B) free radical substitution
(C) nucleophilic addition (C)
8. Ethanol can be formed by the following
reaction:
C2 H 5I + NaOH → C2 H 5OH + NaI
(D)
(A) electrophilic addition
(B) nucleophilic addition
(C) electrophilic substitution
11. 2-hydroxy 2-methylpropanoic acid can be formed from propanone in the two steps illustrated below.
I. Step X involves nucleophilic addition
II. Aqueous potassium cyanide is the reagent in Step X
III. Step Y involves hydrolysis
(A) I only
(B) I and II only
(C) II and III only
(D) I, II and III
12. Which of the following is NOT true of addition polymerisation?
(A) Only one type of polymer is formed.
(B) The molecular mass of the polymer is a multiple of the monomer unit.
(C) The polymer is readily hydrolysed to the monomer.
(D) The physical and chemical properties of the polymer are different from those of the monomer.
13. Which of the following is true for starch and glucose?
Starch Glucose
(A) High solubility in water High solubility in water
(B) Low solubility in water Low solubility in water
(C) Gives blue/black colour with iodine Gives blue/black colour with iodine
(D) No reaction with Fehling’s solution Reduces Cu 2+ in Fehling’s solution to red/brown Cu 2O
Item 14 refers to the following reaction. 16. Which of the following sets of titration
readings is the most precise?
(A) 25.1 25.5 25.1 25.2
(B) 24.9 24.5 25.2 25.4
(C) 25.0 25.0 24.9 24.8
(D) 25.0 24.5 24.8 24.6
14. The product of the above reaction is formed by 17. Which of the following is NOT a property of a
primary standard?
(A) an elimination reaction
(B) electrophilic substitution (A) Does not undergo hydrolysis
(C) free radical substitution (B) Low relative molecular mass
(D) nucleophilic substitution (C) Obtainable in a pure state
(D) Very soluble in water
18. What is the concentration ( moldm )

−3
of an
aqueous solution that contains 63.3g of
K 3Fe(CN)6 in 1.0 dm3 of solution?

Item 15 refers to the following structure –
tyrosine. [The relative formula mass of K 3Fe(CN)6 is 329.2]
(A) 1.92 × 10−1
(B) 2.95 × 10−4
(C) 3.11 × 10−3
(D) 5.77 × 10−1
19. Naturally occurring Element X has four
isotopes: 50 X, 52 X, 53 X and 54 X. They have
percentage abundance of 4.31, 83.76, 9.55 and
2.38 respectively.
What is the relative atomic mass of X?
15. The pH of tyrosine is MOST likely (A) 52.00
(A) 2.1 (B) 52.06
` (B) 5.6 (C) 52.25
(C) 7.0 (D) 53.00
(D) 9.0
20. Treatment of a 10.00g sample containing a 24. Which of the following alkenes has the
chloride salt with excess silver nitrate solution wavelength of maximum absorption λ max .
produces 8.08g of silver chloride.
(Ag = 108, Cl = 35.5) (A)
The expression for the percentage of chloride
in the sample is
35.5 × 10.00
(A) × 100 (B)
108 × 8.08
35.5 × 8.08
(B) × 100
108 × 10.00
35.5 × 10.00
(C) × 100 (C)

143.5 × 8.08
35.5 × 8.08
(D) × 100
143.5 × 10.00
(D)
21. A compound absorbs light of frequency 940 MHz.
The wavelength, in cm, of the light absorbed is
( c = 3.0 × 108
ms -1 )
(A) 31.91 25. Which of the following pairs do NOT absorb
(B) 31.91 × 10−2 infrared radiation?
(C) 31.91 × 10−1 I. H 2O and HI
(D) 31.91 × 10 4
II. H 2 and Cl2
III. NH 3 and HBr
22. Which two features BEST describe ultraviolet

IV. CH 4 and Br2
radiation?
(A) Long wavelength and high energy

(A) I and III only
(B) Long wavelength and low frequency (B) I and IV only
(C) Short wavelength and high frequency (C) II and III only
(D) Short wavelength and low energy (D) II and IV only
23. Which of the following equations governs the 26. Which of the following species is NOT a
determination of an unknown compound, X, in significant fragment from the mass spectrum of
a solution by UV/VIS spectroscopy? ethanol?
(A) log10 ( I0 /I ) = ∈c L (A) C2 H 5OH +
(B) log10 ( I/I0 ) = ∈c L (B) C2H5+
(C) log10 ( I0 /I ) = ∈L[X] (C) CH 3+
(D) log10 ( I/I0 ) = ∈L[X] (D) OH +
27. Which of the following is NOT a stationary 29. A solution of 10g of carboxylic acid (weak
phase used in chromatography. acid) in 100 cm3 of water is shaken with
(A) Alumina 100 cm3 of ethoxyethane. It is found that only
(B) Cellulose 6.5g of the acid remains in aqueous solution at
(C) Silica gel equilibrium. The partition coefficient is
(D) Starch (A) 0.054
(B) 0.54
(C) 5.4
Item 28 refers to the following information.

(D) 54
Sample X is a mixture of substances. X was
separated into its components using paper
chromatography simultaneously with
Item 30 refers to the following apparatus used

individual samples of e, f, g and h. The
in organic preparations.
chromatograph produced is shown below.
Sample X e f g h
28. Which substances are MOST likely present in

30. For which of the following is the apparatus
Sample X?
NOT suitable?
(A) e, f, g
(A) Conversion of phenylamine to
(B) e, f. h benzenediazonium chloride
(C) e, g, h (B) Conversion of butan-1-ol to
(D) e, f, g, h 1-bromobutane
(C) Oxidation of propan-2-ol to propanone
(D) Oxidation of methanol to methanoic
acid
31. Which of the following are important factors to 34. Fermentation of sugars to alcohol is controlled
consider in determining the location of a by a series of enzymes collectively known as
factory? (A) amylase
I. Proximity to a potential workforce (B) lipase
II. Availability to a means of (C) sucrase
transportation
(D) zymase
III. Potential pollution of air, land and
water 35. In the Bosch-Haber process, N 2 and H 2 can be
IV. Proximity to raw materials obtained from X and Y respectively. Which of
the following pairs BEST describes these
(A) I, II and III only sources?
(C) I, III and IV only X Y
(D) I, II, III and IV

Ammonium
(A) Naptha
Salts
32. The extraction of aluminium involves the

Ammonium
electrolysis of purified bauxite dissolved in (B) Air

Salts
molten cryolite, Na 3AlF6 . The MAIN purpose
(C) Air Naptha

of the cryolite is to
Ammonium
(A) prevent the oxidation of the anodes (D) Air
Salts
(B) increase the electrical conductivity of the
melt
(C) reduce the melting point of the mixture

36. Which of the following are consequences of
(D) prevent the reoxidation of the
the assumption of alcohol?

aluminium formed at the cathode
I. Depresses the central nervous system
33. In the fractional distillation of crude oil, the II. May cause liver disease
different fractions are separated based on their III. Reduces manual dexterity
(A) polarity
(B) volatility (A) I and II only
(C) viscosity (B) I and III only
(C) II and III only

(D) solubility
(D) I, II and III
37. In the electrolysis of brine using the diaphragm 41. The presence of phosphate ions ( PO )4
3−
can
cell, two by-products are

be detected using
(A) chlorine and oxygen (A) ammonium molybdate
(B) chlorine and sodium (B) sodium thiosulphate
(C) hydrogen and mercury (C) potassium thiocyanate solution
(D) hydrogen and sodium hydroxide (D) potassium hexacyanoferrate (II) solution
38. Chlorine is the active component for
swimming pool disinfectants, although it is a 42. Chlorofluorocarbons undergo homolytic fission
poisonous gas. Which salt below is used as a by being exposed to ultraviolet light in the
safe chlorine source? stratosphere.
Which radical could result from CH 2 FCF2CL?

(A) HClO
(B) CaCl2 (A) CH 3CF2Cl
(C) NaClO (B) CH2 F •CF2
(D) NaClO3 •
(C) CHFCF2Cl
39. Which of the following industries use (D) CH2 F •CFCl
sulphuric acid?
I. Fertilizer 43. Which of the following statements on
II. Paint environmental effects is true?
III. Fibre (A) Greenhouse effect leads to global
IV. Detergent warming.
(B) Global warming leads to greenhouse
effect.
(B) I, III and IV only (C) Photochemical smog leads to global
warming.
(C) II, III and IV only
(D) Eutrophication leads to greenhouse

effect.
40. The biological oxygen demand (BOD) of water
measures the amount of oxygen
(A) present in a fixed volume of water
(B) produced by aquatic plants in
photosynthesis
(C) needed by microorganisms as they
decompose organic matter
(D) used by aquatic organisms during
respiration
Item 44 refers to the schematic diagram below.
Nitrogen Rain and

N2
Fixation lightning
Nitrifying X
bacteria
Decay Organic N2 Plants
W Y
compounds
Bacteria Bacteria
Z
(A) nitrates
(B) nitrites
(C) nitric (V) acid
(D) ammonium salts
45. The burning of polyvinylchloride, PVC, is considered an improper disposal technique because PVC
(A) forms toxic products
(B) causes acid rain
(C) destroys the ozone layer
(D) has a very high melting point

FOR M TP 2012 155 I·.

CAR IBBE AN EXA MIN ATIO NS COU NCIL

ADVA NCED PROF ICIEN CY EXAM INATI ON

CHEM ISTRY - UNIT 2

Paper 01

90 minutes

( 07 JUNE 2012 (p.m.) )

READ THE FOLL OWIN G INSTR UCTIO NS CARE FULLY .

then1.
1. This test consist s of 45 items. You will have 90 n1inutes to answer

a Data Bookle t.

2. In additio n to this test bookle t, you should have an answer sheet and

(C), (D). Read each · e
3. Each itetn in this test has four sugges ted answer s lettered (A), (B),

you are about to answer and decide which choice is best.

item and shade the s.
4. On your answe'r sheet, find the numbe r which corresp onds to your
the sample item below.

having the san1e letter as the answer you have chosen . Look at

Sampl e Iten1

···.!.
··s·
con1pound?

Which of the follow ing is the HIGHEST energy transiti on in an organic

(A) n to a+ Satnple Answe r

.r
.·; (B) n ton:+
. (C) a to a*

(D) 1t ton:*

been shaded.
The best answer to this iten1 is "a to cr*", so answer space (C) has

your new choice.
5. If you want to change your answer , erase it comple tely and fill in

as careful1y as you can

6. When you are told to begin, tum the page and work as quickly and
to this item later. Your sc
you cannot answer an iten1, go on the next one. You n1ay return
1 .

will be the total nmnbe r of correc t answer s.

7. You tnay do any rough work in this bookle t.

...
_ _J

=
-==
8.
9.
Figure s are not necess arily drawn to scale.
You n1ay use a silent, non-pr ogranu nable calcula tor to answer iten1s.
DO SO.
DO NOT TURN THIS PAGE UNTIL YOU ARE TOLD TO
-==
--
= Copyr ight© 2010 Caribb ean Exami nations Counci l

iiiiiiiiiiil

All rightsr eserve d.
iiiiiiii

I
-2-
3. The compound which shows both ci - rans

1. Which statement is true about C - C bonds?
isomerism and optical isomerism is ----,

I
(A) A double bond is made of a sigma

H H
!
bond and a pi bond.

/
(B) There is a higher electron density

between the atoms in a single
(A) "I c c
I
H I
I
(C)
bond than in a double bond.
The distance between the nuclei
of the carbon atoms is shorter
c
/I'\
"I c C- H
r
'\
H
I
!
H H H
in single bonds than in double H

bonds.
(D) Single bonds are more reactive

I
I
towards most reagents than

I
Cl Cl
double bonds.
'\ /
c= c l
(B) I
Item 2 refers to the following structure.
H H H H.
c
IJ"- H
/
"
/
c --,
H H
I I I I H
H-C-C -C-C-H
I I I l
H H H
H H
H-C-H I I
I
H-C-H
I
(C)
c
"
/
c c
"/ c
I
H
H
II'- H H
Br
2. The IUPAC name for the structure is
(A) 2- ethyl butane
(B) 3 - ethyl butane H H

I
. (C)
(D)
2 - methyl pentane
3 - methyl pentane (D)
c
"
/
c c
"
/j"-
H H H
GO ON TO THE NEXT PA

-3-

4. Volatility of organic compound s depends 6. Which of the following alcohols will N The

on the strength of the inten11olecular forces oxidised by acidified potassium die mate
present. Which compound below would be (VI)?

I:,
the MOST volatile?

(A) CH3 CH2 CH2 0H (A)

(B) CH 3CH2CH2CH3
(C) CH 3CH(CH3 )CH 3

(D) CH3CH2CH2COOH

CH1 0H

I
l
5. In the reaction between ethene and (B) CH- C - H

bron1ine, which statemen ts about the 3 I
reaction mechanism are true?
l

I. A carbocati on forn1s in the rate
OH
H

detennini ng step.
L
II. A dative covalent bond forms
between the bron1ide ion and the (C) CH -CH - C - O H
I

carbocatio n. 3 1 I
I_
III. Heterolyti c fission of the bromine-

CH 3
l_
(A)
(B)
I and II only
I and III only
CH 3
I

(C) II and III only (D) CH- C - OH

I
L
(D) I, II and III 3
CH 3

l_

7. The equation for the fom1ation of the a aes-

thetic, CF3CHBrCl, is
l_
Br2 > CF3CHBrCl

L
The type of reaction occun·ing is

l_
(A) electrophilic substitution

(C) nuc.Ieophilic addition


GO ON TO THE NEXT P r

-4-
8. Ethanol can be fonned by the fo11owing 10. Which of the following compoun oes
reaction NOT give a white precipitate when h ken
with cold ethanolic silver nitrate?
(A)
(A) eJectrophilic addition
(B) nucleophilic addition

Cl

nucleophilic substitution (B)
(D)
I
i
Iten1 9 refers to folJowing diagram of i

I
Compound A. CJ I
(C)
0 I
I
I
II
(D) i
I
nc==cn2
Compound A
I
9. Which statements are cmTect concerning l
Cmnpound A? 11. Which of the foJJowing would rei f a
proton MOST readily?

I. It will decolourize aqueous
bromine. (A) CH 3CH 20H
II. It will decolourize cold, acidified (B) CH.COOH I

·' !
potassimn pennanganate. (C) C"'H 50H
111. It will produce a mirror with (D) CH 30H

Toll en's reagent.
(A) I and Il only 12. Hydrogen cyanide is more likely to i to
(B) I and 11 I only ethanal but not to ethene because I

i
(C) II and JII only

(D) I., II and HI (A) ethanal is more susceptible Ito
e)ectrophilic attack than et
(B) I is more susceptible t tl' jee
rsd1caf attack than ethene 1
(C) ethanal is more susceptib ito

nucleophilic attack than et
(0) the addition product formed '-
ethene would be unstable
.......
1;1
-l
- 5-

. Jten1 13 refers to the following structure of 16. Which of the following may be elimi
I

tyrosine. by calibrating a measuring instrume t I

(A) Lack of precision
(B) Random en-ors

Systematic errors
(C)

(D) Random and systematic erro s 1

I
i

I

'.::i 17 . Which of the following is NOT apr ;rty
l
!'
... ..
·;;:J of a prhnary standard? i
I

(A) Does not undergo hydrolysi 1
j·[
13. The pH of tyrosine is MOST likely (B) Has low relative molecular 's.
(C) Is obtainable in a pure state.

(A) 2.1 (D) Is very soluble in water.

(B) 5.6

(C) 7.0

(D) 9.0 18. Which of the following will NOT

the accuracy of the results in a titri
analysis?

14. Which of the following is NOT true of

addition poly1nerisation? (A) Adding excess water to the c

flask

(A) Only one type of polyn1er is (B) Blowing the reagent out
fon11ed. pipette tip

(C) Overshooting the calibration
(B) The 1nolecular mass of the polymer

is a multiple of the monomer of the volun1etric flask

unit. (D) Purity of reagents

(C) The polymer is readily hydrolysed

to the monomer.
(D) The physical and chetnical 19. A 300 mg solid sample containing ch

properties of the polymer are is dissolved in water. The chloride i

different fron1 those of the precipitated as AgCl by the additi

n1onon1er. silver nitrate to the solution of the sa
The precipitate is collected, washed,

and weighed, and found to have a m

15. The product fanned by the polymerisation of 525 mg.

propene, C 3H 6 , may be used as a

(R.A.M. ofCl = 35.5, Ag = 108)

(A) fuel
(B) liquid The mass of chloride present in the sat

{C) disinfectant

(D) plastic material (A) 74.2 mg

(B) 118.0 mg

(C) 129.9 mg
(D) 208.0 mg

i

GO ON TO THF. NEXT PA fli

-6-
20. Which of the following statements about 24. Hexane will not absorb light in the U
gravimetric analysis is NOT true? region of the spectrum because ther ;s a
(A) Gravimetric analysis is a purely (A) large difference in energy b

quantitative method. the bonding and antib
orbitals
(B) Gravimetric analysis never
involves the removal of volatile (B) large difference in energy b
components of a the bonding and non-b
(C) The analyte can be identified after orbitals

precipitation and isolation have (C) small difference in energy b
the bonding and non-b

occurred.
(D) The amount of analyte lost due orbitals
to solvation is assumed to be (D) sma11 difference in energy b
negligible. the bonding and antibo

orbitals
21. Which of the following analytical tech-
niques is considered MOST specific for 25. Which of the following pairs will NOT
identification purposes? infrared radiation?
(A) Mass spectroscopy I. H:! and Cl 2
(B) UVNIS spectroscopy II. NH 3 and HBr
(C) Gas chromatography III. CH4 and Br1
(D) Thin-layer chromatography
(A) I only
(B) 11 only
22. Which two features BEST describe ultra- (C) I and III only
violet radiation? (D) II and III only
(A) Long wavelength and high energy
(B) Long wavelength and low 26. Which of the following statements ab
frequency patiition coefficient may be true?
(C) Short wavelength and high
l. It does not vary with temperat r ;.

(D) Shot1 wavelength and low energy I1. The so Jute has to be in the ,1pe
molecular state in both sol e.nts
for it to be a constant.
23. Which ofthe following types of electronic HI. The two solutions have be
transitions would NOT produce absorption con centra ted for it to <i' a
in the UVNIS region ofthe spectrum? constant.
(A) s __... p* (A) I only
(B) p-+ p"' (B) 11 only
(C) n __... p* {C) J and l1 only
(D) n-+ s* (D) I. II and Ill
-...,

-7-

27. Which of the follow ing is NOT a station ary 30. Which of the followi ng are advant g is of

phase used in chron1 atograp hy? stean1 distilla tion? I

I
(A) Alumi na I. It occurs under reduce d pre

(B)
(C)
Cellulo se
Silica gel
II.
Ill.
The compo nents do not deco
It provid es saving s in fuel t.

(D) Starch i

(A) I and II only

(B) I andl Ill only
··
Item 28 refers to the followi ng inform ation. (C) II and III only
...j
I (D) I, 11 and III

A studen t canies out an experim ent using I

thin-la yer chron1 atograp hy separat ion on
I

silica gel and obtains the follow ing results: 31. Which of the following are important
to conside r in detenni ning the locati 1 ?f a

factory? i
Compo und Distan ce Travel led

(em)
I

Compo und A 1.5 I. a potential work

II. Avail ability to a mea s iI of
Compo undB 9.1 .
,
transpm 1atwn

Solven t 12.5
III. Potenti al polluti on of air, lat · nd

water
28. The Rr value of Compo und A is

IV. Proxim ity to raw materials

(A) 0.07

(B) 0.12

(C) 0.16
(C) I, Ill and IV only
(D) 0.73


29. A solutio n of 10 g of a carbox ylic acid 32. Along with silicon dioxide , which

(weak acid) in 100 cm 3 of water is shaken
following compou nds constitutes the
with 100 cm of ethoxy ethane . It is found
3

that only 6.5 g of the acid remain s in

aqueou s solutio n at equilib rimn. The (A) lron(II) oxide

pa1tition coefficient is lron(IIJ) oxide
(B)

(C) Carbon dioxide

(A) 0.054
(D) Carbon monoxide
(B) 0.54

(C) 5.4

(D) 54.0

GO ON TO THF. NF.XT PAr,

-8-
Item 33 refers to the follo wing fractions of 37. In the elec troly sis of brin e u ing the·
crud e oil. diap hrag m cell, two by-p rodu c s re
Dies el (A) chlo rine and oxyg en
I.
(B) chlorine and sodium
II. Petrol
Refin ery gas (C) hydr ogen and merc ury

III.
IV. Kero sene (D) hydr ogen and sodi um h
33. The corre ct orde r in tenn s of INCR EAS ING

boiJing poin ts is 38. The pres ence of phos phat e ions ( . 4J-) can
be detec ted usin g
(A) I, II, Ill, IV
(B) III,I ,IV, II (A) amm oniu m moly bdat e

pota ssiu m hexa cyan o ate( II)
l
III, II, IV. I (B)
(C)
solut ion
IV, II, I, Ill
(D)
(C) pota ssium thioc yana te s J
1
tion
(D) sodiun1 thios ulph ate
l
I
34. Whi ch of the follo wing prod ucts is NOT
prod uced for comm ercia l purp oses by the II p I11tes

.
39. C mnp oun ds o f· su lP.I sue I1 .as.
e]ectroJysis of conc entra ted brine ?

are used as food addi tives . This 1 .ecause
1
(A) Chlo rine they I
(B) Oxyg en I
(A) impr ove the flavo ur of ft i
(C) Hydr ogen

food
Sodi um chlor ate (V) (B) help to enha nce the colo
(D)
(C) inhib it the oxid ation ofun a: trated
fats
help to pres erve the by
35. In the Bosc h-Ha ber proc ess, N., and can (D)
dehy drati on
be obta ined from X and Y

T
Whi ch of the follo wing pair s BES

desc ribes X and Y?
40. Whi ch of the follo wing use
X y sulph uric acid'?
(A) Amm oniu m salts Naph tha I. Fet1ilizer

-
Air n. Paint
(B) Amm oniu m salts
(C) Air Naph tha IIJ. Fibre
(D) Air Amm oniu m salts

IV. Dete rgent
I. II and Ill only

(A)
(B) 1, Ill and lV only
36. Whi ch of the follo wing state men ts does (C) II, Ill and JV only
ol
NOT accu rateJ y desc ribe a resul t of ethan L 11, JH and JV
consumption?
(D)
(A) Dige stion occu rs in the stom ach.
(B) Natu ral inhi bitio ns are re]ax ed

(redu ced) .
Oxid ation occu rs in the bloo d.

(C)
(D) Reac tion time is redu ced.
GO ON TO THE NEX T P Cftf.
-9-

. Item 44 refe rs to the follo win g sch
1 atic
I.

'.·
41 . Whi ch of the follo win g is NO T a gree
hou se gas?
n-
diag ram .

(A) Amn 1oni a Nitrogen _., N2

(B) Car bon diox ide fixation ...-l J lightning Li
!X

(C) Met han e Deni trifying J
Wat er vap our
l
(D) bacteria Nitrifying

) bacteria

,

Item s 42- 43 refe r to the foll owi ng Organic Plants y

desc ripti on: f
wr. .._D eca y. N
2
4 I
J
i.i
compounds

Aer oso l prop ella nts such as Freo
n-11 ,
Bacteria I

CC13 F, are of 111ajor con cern beca use of Bacteria ...
I
with ozon e,

thei r photochen1icaJ reac tion
the strat osph ere

.ii,i· 0 3 • Ultr avio let radi atio n in
th(m W would MO ST JikeJy be
j
prod uce s chlo rine radi cals , whi ch 44.
reac t with ozon e, prod ucin g oxy gen.

(A) nitrates
cal nitrites

42. A bala nced equa tion for the pho toch emi
(B)
Freo n- II is (C) nitri c(V) acid

deco n1po sitio n of
J:l,
(D) amm oniu m salts

(A} CC13F(g) hr ) 2Cl• (g) + CCI F•

re

45. Wh ich of the foll owi ng plas tic
·:t.f•. t;;:.:·1
hr > CCl •(g) + F•(g ) :
··;o-.:,-•·
(B) CC13F(g) biod egra dabl e?

3 .
1
J1t

(C) CC13 F(g) hf ) Cl•( g) + CCl F•(g )
2
(A) Low dens ity poly ethe ne

(B) Poly then e tere phth alate .
-·I
1
Po1y (3 - hydr oxyb utan o1c ac dO

(D) CC13F(g)
hr ) 3Cl• (g) + CF• (g) (C)
I
(D) Poly viny lchl orid e

i
_j
·. 43. A bala nced equa tion for the prod ucti
on of
oxy gen from ozo ne is

0 1(g) + Cl·(g)---.. O(g ) + CIO , •(g)

_j
(A)
(B) + Cl•(g)---.. CIO •(g) + 0 7 (g)
(C) + CI-(g) O(g ) + ClO.,:(g)

(D) + CI-(g)---.. O.,(g) + CJO -(g)

END OF TES T

CH EC K YO Uil WO RK ON TH IS
TE .

.......'il..... .•• ;s ...:,J;..•
ntr " nu " l n l "l

I . .
TESTCODE02212010.
MAY/JUNE 2013
CARIBBEAN ADVANCED PROFICIENCY EXAMINATION®
r
CHEMISTRY - UNIT 2
!
Paper 01
1 hour 30 minutes
( 11 JUNE 2013 (p.m.) )
READ THE FOLLOWING INSTRUCTIONS CAREFULLY.
I. This test consists of 45 items. You will have I hour and 30 minutes to answer them.
2. In addition to this test booklet, you should have an answer sheet and a Data Booklet.
3. 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.
4. 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.
Sample Item
Which of the following transitions requires the HIGHEST energy in an organic compound?
(A) n to cr• Sample Answer
(B) n ton•
(C)
(D)
n to n•
cr to a•
@®©•
The best answer to this item is "cr to cr•", so answer space (D) has been shaded.
5. If you want to change your answer, erase it completely and fill in your new choice.
6. When you are told to begin, tum the page and work as quickly and as carefully as you can. If
you cannot answer an item, go on to the next one. You may return to this item later. Your score
will be the total number of correct answers.
1: You may do any rough work in this booklet.
--
--
9. You may use a silent, non-programmable calculator to answer items.
--
__ ,_
= DO NOT TURN THIS PAGE UNTIL YOU ARE TOLD TO DO SO.
Copyright© 20 I 0 Caribbean Examinations Council
All ripu ret«Ved.
-2-
refers to the following diagram. s. 'Which of the following compounds is hydro-
lysed by water? .
©"'r-NH 2
(A) C,H,OH
CH3
1. Based on the IUPAC rules, the name of the (8)
compound above is
(C) C6 H,CH,CI
(A) I -phenylpropan-2-amine
(B) l-benzylpropan-1-amine (D) ---<Q>-CH,CI
.(C) I -phenylbutan-2-amine
(D) 1-phenylbutan-1-amine Item 6 refers to the following information.
A substance reacts with

l. A hydrocarbon contains 87.8% carbon and
12.2% hydrogen by mass. Its empirical I. NaOH to fonn an ionic product
fonnula is II. PCI,, giving off HCI
Ill. H, in the presence of a nickel
(A) CH catalyst
(B) · CH, IV. ethanol to produce an organic

(C) C,H, compound and water
(D) C,H,
6. The substance with the properties above
could be
3. An electrophile has
0
(A) a positive charge (A) II
(B) a negative charge CH,-C-H
(C) a non-bonding electron

0
(D) an oxygen or nitrogen atom

(ll) II
CH,-C-OH
4. Which of the following tenns does NOT
0
describe a nucleophile? (C)
II
CH, =CH-C-OH
(A) Lewis acid

(8) Lewis base
(C) Species with a lone pair (D) CH,= CH -CH 2 -0H
(D) Electron donor
(',()ON TO·THF. NF.XT PA.OF
-3-
7. Methylbenzene, tbi ,
CH 3
can react to 9. A compound, X, reacts with
+
I. 2, 4-dinitrophenylhydrazine
CH 3
(DNPH) to give an orange
precipitate
produce IL Tollen's reagent to give a silver

mirror
aqueous alkaline iodine to give

Cl Ill.
yellow crystals.
Which of the following reagents and

conditions are MOST suitable for the
Compound X is MOST likely

reaction?
(A) CH3
(A) Chlorine with AICl 3
(B) Chlorine in the dark

(C) Chlorine with UV light @-CHO
(D) Concentrated HCI heated under
reflux
(B) CH2 COCH 3
8. Diazonium salts are useful in the synthesis @-oa

of aromatic oompounds. Which of the
compounds below can be prepared from a
diazonium salt? (C) ce,
©r-CH(OH)CH 3
COOH
(A)
© (D) CH2 COCH 3
@-cao
(B)
N )!)
(C) ©" N 10. Which of the following compounds wilf

NOT decolourize bromine water but will
decolourize potassium manganate(Vll) on
(D) warming?
(A) Butane
(B) Ethanol
(C) Ethene
(D) Ethanoic acid
00 ON TO THE NEXT PAGE
-4-
11. Which of the following pairs of compounds are optical isomers?
CH, CH3
I I
(A) CH1 -C-OH HO-C-CH3
I I
CH, CH,
H H
I I
(B) C,H,-C-OH HO-C-C,H,
I I
CH3 CH,
H. H H H H H H H
I I I I I I I I
(C) H-C-C-C-C-OH HO-C-C-C-C-H
I I I I I I I I
H H H H H H H H
CH1 H H CH,
I I I I
(D) H-C-C-OH HO-C-C-CH,
I I I I
CH3 H H CH,
12. The complete reaction of phenol with aqueous bromine is characterised by a
(A) brown precipitate, a brown solution and a sweet smell
(B) brown precipitate, a colourless solution and a swec;t smell

(C) white precipitate, a colourless solution and an antiseptic smell
(D) white precipitate, a brown solution and an antiseptic smell
-5-

13. Which of the options below, (A), (B), (C) and (D), is correct for the properties shown by the

following structures?

OH

0

I

0 n-c-a
I
H

(A) Negative inductive Positive inductive Conjugative
effect effect ·effect

(B) Conjugative Negptive inductive Positive inductive


(C)
. Negative inductive
effect
Conjugative
effect
Positive inductive
effect

(D) Positive inductive Conjugative Negative inductive


Which of the following statements is NOT
14. 16. Which of the following factors will NOT

true about condensation polymerization? affect the accuracy of the results in a

titrimetric analysis?

(A) The molecular mass of the polymer

is a multiple of the combined (/\) Purity of reagents
masses ofits monomers. (B) Adding.excess water to the conical

(B) The polymer can be hydrolysed to flask

form its monomers. (C) Blowing the reagent out of the

(C) The polymer has physical and pipette tip

chemical properties that differ (D) Overshooting the calibration mark
from the monomer units. of the volumetric flask

(D) Small molecules are eliminated

during the condensation process.

17. Which of the following instruments is NOT

used in titrimetry?

15. The product formed by the polymerisation
of propene, C3 H6, may be used as a (A) Barometer

(B) Thermometer

(A) fuel (C) Potentiometer

(B) liquid (D) Conductivity meter

(C) disinfectant
(D) plastic material

!'
00 ON TO THE NEXT PAOE
l-l'
'r
;-_- • =

.-

-6-
18. Which of the following graphs illustrates the titration of dilute sulfuric acid with potassium
hydroxide solution?
(A) 14 (B) 14
pH pH
Vol ofH, SO, Vol ofH 2 SO,
14 (D) 14
(C)
pH pH
7 7
Vol ofJI,804 Vol ofH2 S04
Items 19=20 refer to the following information.
A student carries out the gravimetric analysis of a soil sample taken from an area surrounding a
garage. The soil sample is found to be contaminated with Pb'• ions. I 00 cm' of a solution obtained
from the sample when mixed with 25 cm' ofO. I 00 mol dm-' HCI yields 0.010 g of lead chloride.
[The relative formula mass of lead chloride is 278.2.J
19. The balanced equation for the reaction between lead ions and hydrochloric acid is
(A) Pb (s) + 2HCI (aq)-+ PbCl 2 (s) + H, (g)
(B) 2Pb (s) + 2HCI (aq) -+ 2PbCl (s) + H, (g)

(C) Pb,. (aq) + 2HCl (aq)-+ PbCl2 (aq) + 2W (aq)
(D) Pb2• (aq) + 2HCI (aq)-+ PbCI, (s) + 2H' (aq)
20. What is the concentration of Pb'• in the original solution?
(A) 3.60 >< I 0-' mol dm-3
(B) 3.60 x Hr' mol dm-'
(C) 5.40 >< IO_. mol dm-'
(D) 7.20 x JO-' mol dm-'
- 7-
21. The complex ion [FeSCNJ2• has a molar 23. The structural features which cause
absorptivity(E)of 7.0x IO'dm'mol- 1 cm- 1• . absorption in the. UV NIS region of the

electromagnetic spectrum known as
The concentration of its solution, which
gives an absorbance of 4.2 when measured (A) er bonds
in a 2-cm cell, is (B) chromophores
(C) isolated 1t bonds
(A) 3 x 10-3 mol dm-3 (D) lone pairs of electrons

(B) 6 x I 0-3 mol dm-3
(C) 3 x lQ-4 mol dm-3
(D) 6 x 1Q-4 mol dm·' Item 24 refers to the diagram below
which represents the structure of a water

molecule.
22. Which of the following regions of the
/"
electromagnetic spectrum BEST matches 0-+
the wavelength ranges of P, Q and R?
H H
Frequency CH2)
10"
"'
24. Which of the following vibrations may be
exhibited by the molecule?

p Q R
(A) Bending only

(B) Bending and stretching
p Q R
(C) Symmetrical stretching only
(A) UV IR radio (D) Asymmetrical stretching only
(B) IR UV radio
(C) IR UV x-rays
(D) UV IR x-rays
25.
(A)o '"'O (C)o

Which of the following alkenes has the wavelength of maximum absorption, A,."' ?
-8-
26. A mixture of gases containing methanol, 30. Which of the following statements about
ethanol, propan-1-ol and propan-2-ol, was partition coefficient would be true?
obtained from a refinery. What method can

I. It does not vary with temperature.
be used to separate these gases for analysis?

II. The solute has to be in the same
molecular state in both solvents for

(A) Mass spectroscopy
(B) IR spectroscopy it to be a constant.
(C) Gas-liquid chromatography Ill. The two solutions have to be
(D) High pressure liquid chroma- concentrated for it to be a constant.
tography (A) I only
(B) II only
27. Which of the following compounds do

(C) I and II only
(D) I, II and HI
NOT absorb infrared radiation?
I. H20and HI 31. Sulfur contaminated coal is usually mixed

II. H, and Cl, with calcium carbonate at high temperatures to
Ill. N, and Br2 reduce SO, emissions. Which reaction(s) will
be important in helping to reduce atmospheric
(A) . I and II only pollution?
(B) I an<l lll only
(C) II and Ill only I. CaCO, +so, - Caso,+ co,

(D) I, II and III n. 2caco,+2so,+o,-2easo,+co,
Ill. Cao + CO - CaCO,
28. Which of the following species is NOT

(A) I only
a significant fragment from the mass

(B) I and II only
spectrum of ethanol?
(C) II and Ill only
(A) OH'
(D) I, II and lll
(B) CH,·
(C) C,H," 32. Which of the following is represented by
(D) C,H,OH" C, - C, hydrocar.bons?
(A) Diesel oil
29. Which of the following entities is NOT a (B) Gasoline
visualising agent in chromatography? (C) Kerosine
(D) Refinery gas
(A) Cellulose
(B) Iodine
(C) Ninhydrin
33. Which of the following may be a result of
light-induced reaction of pollutants in the air?

(D) Ultraviolet light
I. Global warming
II. Photochemical smog
Ill. Greenhouse effect
(A) I only
(8) II only
(C) I and Ill only
(0) I, II and Ill
GO ON TO TitE NEXT PAGE
-9-
34. Fermentation of sugars to alcohol is 38. For which TWO of the following industrial
control led by an enzyme complex (mixture) products is chloriqe MOST widely used in
known as their manufacture?
(A) amylase I. Solvents
(B) lipase II. Sodium chloride

(C) sucrase 111. Polyvinylchloride
(D) zymase IV. Chlorofluorocarbons
35. In the manufacture of chlorine by the (A) I and II
electrolysis of brine using the diaphragm (B) I and Ill
cell, the anode is made of (C) II and Ill

(D) II and IV
(A) steel
(B) graphite
(C) platinum with a coating of asbestos 39. The burning of polyvinylchloridc, PVC, is
(D). titanium with an inert coating considered an improper disposal technique
because PVC
36. In the production of sulfuric acid by the (A) causes acid rain
Contact. Process, the following exothermic (B) destroys the ozone layer
reaction takes place: ( C) forms toxic products

V,O, (D) has a very high melting point
2SO,(g) + O,(g) > 2SO,(g)
Which of the following condition(s) would

favour the forward reaction? 40. Which of the following ions are significant
contributors to eutrophication?
I. Low pressure
II. Excess oxygen I. PO/-
Ill. Low temperature II. NO,-
III. so.i-
(A) I only
(B) I and II only IV. c1-
(C) II and III only
(D) I, II and III

(A) I and II only
(B) I and Ill only
37. Flocculation is a process involved in the

(C) I, II and Ill only
(A) clarification of water
(B) cleaning of the fumes in the Haber

41. The presence of phosphate ions (PO/") can
Process
be detected using
(C) conversion of excess S02 gas in the
contact process into MgSO4 (A) ammonium molybdate
(D) .. production of ethanol by (B) sodium thiosulfate
fermentation (C) potassium thiocyanate solution
(D) potassium 'hexacyanoferrate(ll)
solution
00 ON TO THE NEXT PAGE
- I0 -
42. When chlorofluorocarbons in the upper 44. . Nitrogen monoxide, NO, is responsible for
atmosphere are impacted by ultraviolet the destruction of ozone in the stratosphere.
radiation, chlorine radicals are formed in How is NO generated in the· atmosphere?
preference to fluorine radicals. This occurs
in the upper atmosphere because the energy L Combustion of fossil fuels
of the Il. Lightning discharge

III. Reduction ofN02 by S02
(A) C-F bond (484 kJ mol- 1) is greater
than the energy of the ultraviolet (A) I and II only
radiation (B) I and Ill only
(B) C-CI bond (340 kJ mol- 1) is greater (C) II and Ill only
·than the energy of the ultraviolet (D) I, II and Ill

radiation
(C) C--CI bond is less than the energy
of the C-F bond 45. Which of the following plastics are
(D) C-CI bond corresponds to the biodegradable?
energy ofthe ultraviolet radiation

43. Chlorofluorocarbons undergo homolytic (C) Poly (3 - hydroxybutanoic acid)
fission by bc:ing exposed to ultraviolet light (D) Polyvinylchloride
in the stratosphere.
Which radical could result from
CH,FCF,CI?
(A) ·cH,CF,CI
(B) CH,FCF,·
(C) "CHFCF,CI
(D) CH,F ·cFCI
END OF TEST
IFYOU FINISH BEFORE TIME IS CALLED, CHECK YOUR WORK ON THIS TEST.
%.
PRINT your trlnc on tbc lin! bclo* rnd rctum
thir booklet wlth your rnrwcr sbcrA Frllurc to
do so nry rcsult in dhqurllficrtlon coDE 02212010
FORM TP 2014152 MAY/JUNE 20I4
CARIBBEAN ADVANCED PROFICIBNCY EXAMINATION@
CHEMISTRY_ UNIT 2
Paper 0l
I hour 30 minutes
l0 JUNE 2014 (p.m.)
|. This test consists of 45 items. You will have I hour and 30 minutes to answer them.
2. In addition to this test booklet, you should have an answer sheet and a data booklet.
3. Each item in this test has four suggested answers lettered (A), (B), (C), (D).

Read each item
1' 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 atihe
sample item below.
Sample ltem
Which of the following is the HIGHEST energy transition in an organic
compound?
(A) n to o* Sample Answer
(B) o to o*
(C) n to 7r+
(D) n to rr'r, @o@@
The correct answer to this item is "o to o*", so answer space (B) has been shaded.
5. lf you want to change your answer, erase it completely and fill in your new choice.
6. when you are told to begin, turn the page and work as quickly and
as carefully as you can. If
you cannot answer an item, go on to the next one. You

may retum to this item later. your score
will be the total number of correct answers.
9. You may use a silent, non-programmable calcurator to answer items.
-I ARE TOLD TO DO SO.
-
I Copyright,.O 20 l2 Caribbean Examinations Council
II-
I All rights reserved.
022t20tOicAPE 20t4
-
r-

2-
The ideal detectorused in gaschromatography
l. Combustion analYsis of 0'lt g of an 4.

Which of
organic compound produces 0'396 g of tOCl n* specific characteristics'

dioxide and 0.216 g of water' The
itt" iottorring characteristics are for a GC
"utton detector?
empirical formulaof the compound, given

tt it contains carbon, hydrogen and
"i
oxygen only, is
t. Adequate sensitivitY
ll. Good stabilitY
(A) C,HP lll. Short resPonse time
tV. EasY to use

(B) c{Hso
(c) c,HPn (A) I and ll onlY
(B) | and lll onlY
(D) C6H,P,
(C) I,lI and lV onlY
(D) l,ll,lII and IV
2. Which of the following compounds show
optical activity?
5. Which of the following statements about
polyunsaturated oils (trigylcerides) is
r. cHscH(oH) cooH
FALSE?
Il. HOCH = CHOH
il. cH3cH(cl) cHr (A) They undergo saPonificaton.
ry. HC(Br) I Ct
(B) They are hYdrolYsed to Producc
diglYcerides.
(A) I and II only (C) Thcirshelflivcsareprolongedwith

hydrogenation.
(B) I and IV only (D) They aru hydrogenated to produce
(C) II and III only margarine.
(D) III and IV only
3. Volatility of organic compounds OepenOs on
the strength of the intermolecular forces

present. Which compound below is the
MOST volatile?
(A) cHscH2CH2OH
(B) cHrcH2cH2cH3
(c) cH3CH(CH3)CH,
(D) cHpHrcH2cooH
/:^ Tr) THF NEXT PACE

3-
6. Which of the 'following alcohols will Item I refers to following diagram of

NOT be oxidized by acidified potassium Compound J.
dichromate(Vl)?
9Ht
CTI ,oH
(A)
cH2oH
(B) cHr-i-n I
HC
-
CH2
I
Compound J
OH
8. Which of the following statements are

correct concerning Compound J?
I. lt will decolourize aqueous
(c) CH, _ CHr_ _ o"

I
bromine.
f I
II. It will decolourize cold. acidified
potassium perrnanganate.
CH,
III. It will produce a silver mirror with

Tollen's reagent.
(D) l''
cH,-i-o"
(A)
(B)
I and ll only
I and III only
(c) ll and III only

(D) l, II and III
CH,
Item 9 refers to the compounds, B e, R and
7. In the reaction between ethene and S, whose structures are given below.
bromine, which statements about the
reaction mechanism mav be true? P: CH,(CH,)4CH2OH
Q: CHr(CH,)3CH,COOH
l. A carbocation forms in the rate

determining step. R: CH3(CH2)TCHCICOOH
ll. A dative covalent bond forms S: C6H5OH
between the bromide ion and
ethene.
lll. Heterolytic fission of the bromine- 9. The correct sequence of the compounds
bromine bond occurs. above, in order of DECREASING acid

strength, is
(A) l only
(B) | and Il only (A) P, S, Q, R
(C) Il and lll only (B) Q, R, S, P
(D) l. II and lll (c) R. Q, S, P
(D) S, R. Q, P
GO ON TO THE NEXT PACE

4-
ll. The complete reaction of phenol with

10. Which of the following compounds does
aqueous bromine is characterized by a

NOT give a white precipitate when shaken
(A) white precipitate, a colourless
(A) 9H' solution and an antiseptic smell

(B) brown precipitate, a colourless
+-.,
ct
(c)
solution and a sweet smell
white precipitate, a brown solution
and an antiseptic smell
(D) brown precipitate, a brown solution
(B) cH2cl and a sweet smell
a
I
12. Which ofthe following organic compounds
I
cl would release a proton MOST readily?
(c) cHct2 (A) cH3cH2oH
I
(B) cH3cooH
@ (c) c6H5oH
(D) cH3oH
(D)
f+ct
I
crrcl2
Item 13 refers to each of the three sets of structures shown below which are to be labelled as
showing the conjugative effect or the positive inductive effect or the negative inductive effect.
OE
0-v
,t
rA H
o
I
H- c->cl
I
13. Which of the following options has the labels in the correct order to match the structures?
(A) Positive inductive Conjugative Negative inductive
(B) Conjugative Negative inductive Positive inductive
effect etfect effect
(c) Negative inductive Conjugative Positive inductive
(D) Negative inductive Positive inductive Conjugative

etTect
efTect efTect

5-
ln gravimetric analysis of a substance

14. Which ofthe following statements is NOT 18.
true of addition polymerization? by precipitation, which of the following
outcomes would be FALSE for the
(A) Only one type of polYmer is precipitate fbrmed?
fbrmed.
(B) The molecular mass ofthe polYmer (A) It would be easily filtered and
is a multiple of the monomer washed free of contaminants.
(B) Its composition would not have to

unit.
(c) Ihe polymer is readily hydrolyzed be known.
to the monomer. (c) It would be unreactive with the
(D) Ihe physical and chemical atmosphere.
properties of the polymer are (D) It would be essentially insoluble to
different from those of the prevent loss during washing.

monomer.
19. A 300-mg solid sample containing chloride

is dissolved in water. The chloride is then
15. The product formed by the polymerization

of propene, CrHu, may be used as a precipitated as AgCl by the addition of
silver nitrate to the solution of the sample.
(A) fuel The precipitate is collected, washed, dried
(B) liquid and weighed, and found to have a mass of
(C) disinfectant 525 mg.
(D) plastic material

(RAM of Cl = 35.5, Ag = 108)
16. Which of the following inaccuracies may The mass of chloride present in the sample is
be eliminated by calibrating a measuring
instrument? (A) 74.2 mg
(B) I 18.0 mg
(A) Lack of precision (C) 129.9 mg
(D)
(B) Random erors 208.0 mg
(C) Systematic errors
(D) Random and systematic errors 20. In an electronic transition in the UV/visible
region of the spectrum, a wavelength of
450 nm is absorbed.
17. The concentration of an ammonia solution
is determined by titrating25.0 cmr against

Planck constant (h) = 6.61 x l0'3a J
0.2 mol dm-r sulfuric acid to eive an end

s
Velocity of light (c) = 3.00 x l0E m
s-r
point of 27.5 cmr.
The energy of the corresponding photon (in
The concentration of ammonia Joules) is

(in mol dm-3) is given by
0.2 x 27.5 (A)

66.3x10-roxl08
(A)
25
4.50 x l0-5
0.2 x 27.5 (B)

4.50 x l0-7
(B) 6.63 x lO-ra x 3 x 108

2x25
2x0.2x27.5 6.63 x l0-ra x 3 x 108

(c) (c)
25 4.50 x l0-e
'2x0.2x25 6.63x l0-rox3x 108
(D) (D)
27.5 4.50 x l0-?

6-
21. The structural'features which cause absorption in the UV/VIS region of the electromagnetic
spectrum are known as
(A) o bonds
(B) chromophores
(C) isolated n bonds
(D) lone pairs of electrons
22. which of the fbllowing alkenes has the wavelength of maximum absorption, 1,n'.*?
t,o
(A) (B) (c)
23. An unknown organic compound with molecular mass of 44 g is analysed using infrared. The
bonds are found at 1700 cm-r and 2800 cm-r.
The compound is MOST likely
(A) ethanal
(B) ethanol
(C) ethanoic acid
(D) carbon dioxide
24. which of the following analytical techniques is considered MOST specific for identification
purposes?
(A) Mass spectroscopy
(B) UV/VIS spectroscopy

(C) Gas chromatography
(D) Thin-layer chromatography
.-:l^r |^lN Tn TIJtr l\ttr].T pA ntr

25. Which of the following pairs ofcompounds Item27 refers to the following information.
do NOT absorb infrared radiation?
A student carries out an experiment using
t. H,O and HI thin-layer chromatography separation on
il. H, and Cl" silica gel and obtains the following results:
III. NH, and HBr
Compound Distance Travelled

tv. CH. and Br, (cm)
Compound A
(A) I and lll only

1.5
Compound B 9.1
(B) I and lV only Solvent 12.5
(c) II and III only
(D) II and IV only

27. The Rrvalue of CompoundA is
Which of the following media is NOT a

(A) 0.07
26.
(B) 0.t2
visualising agent in chromatography?

(c) 0.16
(D) 0.73
(A) Iodine
(B)
Cellulose
(c) Ninhydrin
(D) Ultraviolet light
Item 28 refers to the following boiling point-composition curves for three mixtures, I, II and III.
28. Which of the following mixtures CANNOT be completely separated by fractionaldistillation?
(A) I only
(B) II only
(c) I and ll only
(D) ll and III only

29. Which of the. following statements about 31. Along with silicon dioxide, which of the
tbllowing compounds constitutes the main

the partition coefficient may be true?
l. lt does not vary with temperature.
ll. The solute has to be in the same (A) lron(ll) oxide
molecular state in both solvents (B) lron(lll) oxide
for it to be a constant. (C) Carbon dioxide

lll. The two solutions have to be (D) Carbon monoxide
concentrated fbr it to be a
constant.
Item 32 ref'ers to the following fractions of
(A) lonly crude oil.
(B) ll only
(C) | and II only l. Diesel

(D) I, II and lll Il. Petrol
lll. Refinery gas
IV. Kerosene
Item 30refers to the following apparatus
used in organic preparations. 32. The correct order in terms of increasing
boiling point is
(A) l, ll, lll, lv
(B) III. I, II, IV
(c) III, II, I, IV
(D) ilt, II, IV I
33. The essential conditions for the Haber
process are
(A) 2Atm pressure,400.C, iron catalyst
(B) 2Atm pressure, 450 "C, no catalyst
30. For which of the following processes is the (C) 200 Atm pressure, 450 'C, iron
apparatus NOT suitable?
catalyst
(D) 200 Atm pressure. 1000 "C, no

(A) Conversion of phenylamine to catalyst
benzenediazon ium ch loride
(B) Conversion of butan - | - ol to
I - bromobutane Item 34 refers to the manufacture of
(C) Oxidation of propan - 2 - ol to chlorine by the electrolysis of brine using

propanone
the diaphragm cell.

(D) Oxidationofmethanoltomethanoic
acid 34. The anode is made up of
(A) steel
(B) graphite
(c) platinum with a coating of asbestos
(D) titanium with an inert coating of

ruthenium(lV) oxide
CO ON TO THE NEXT PAGE

9-
35. For which TWO of the following industrial 38. In which of the following industries is
products is chlorine MOST widely used sulfuric acid used in the development of
during their manufacture? their products?
l. Solvents I. Fertilizer
ll. Sodium chloride II. Paint
Ill. Polyvinylchloride lll. Fibre
lV. Chlorofluorocarbons lV. Detergent
(A) I and ll
(A) I, II and lll only

(B) I and lll (B) [, lll and IV only
(C) ll and lll (C) Il, III and lV only
(D) ll and IV (D) I, II, III and IV
36. In the production of sulfuric acid by the
Contact process, the following exothermic 39. Which of the following ions are significant
reaction takes place: contributors to eutrophication?
I.
Oz(g) i v'o' 4'?0'c'
POnr-
2SOr(g) + "t\ 2SOr(g)

'z
II. NOr-
Which of the following conditions would III. SOor-
favour the forward reaction?
IV. cl-
I. Low pressure
II. Excess oxygen (A) I and II only
ilr. Low temperature (B) I and III only
(c) III and IV only
(A) I only (D) I, II, III and lV
(B) I and II only
(c) II and III only

(D) I, ll and III
37. Compounds of sulfur such as sulfites are
used as food additives because thev
(A) help to preserve the food by
dehydration
(B) inhibit the oxidation of unsaturated
fats
(c) help to enhance the colour of food
(D) improve the flavour of food
Nr) r)N Tr| THtr \ItrYT DA'-:tr

l0 -
Items {0-41 refer to the following 43. Which of the fbllowing compounds is NOT
information. a primary pollutant?
Aerosol propellants such as Freon-ll, (A) Nitrogen dioxide
CC|.,F, are of major concern because of (B) Carbon monoxide
their photochemical reaction with ozone. (C) Nitrogen monoxide

Or. Ultraviolet radiation in the stratosphere (D) Sulfur dioxide
produces chlorine radicals. which then
react with ozone. producing oxygen.
{.1. Which of the tbllowing resources are
40. A balanced equation fbr the production of normally associated with the formation of
oxygen from ozone is photochemical smog?
(A) O.,(g) + Cl.(g)--'* O(B) + Clo2.(g) t. Nitrogen oxides
(B) O.,(g) + Cl.(g) --- ClO.(g) + O.(g) il. Sunlight
(c) or(c) + Cllg) --- O(g) + Clo:-(g) il. Volatile organic resources
(D) o,(e) + Cl (g) -- O,(g) + Clolg)
(A) I and Il only
(B) I and lll only
41. A balanced equation for the photochemical (c) ll and lll only
decomposition of Freon- | | is (D) l, ll and lll
(A) CCIrF(g) ht , 2Cl.(g)+ CCIF.
45. Which of the following plastics is
biodegradable?
(B) ccl,F(g) hr ), cct3.(g) + F.(g)

(A) Low density polyethene
(c) CCIrF(g) ht , Cl.(g) + CCl"F.(g) (B) Polythene terephthalate
(C) Poly (3 - hydroxybutanoic acid)
(D) ccl.F(g) ht ,3c1.(g) + CF.(g) (D) Polyvinylchloride
12. Chlorofl uorocarbons undergo homolytic
fission by being exposed to ultraviolet light

in the stratosphere.
Which radical could result from
cH,FCF,Cl?
(A) CH,F'CF,
(B) 'CH,CF,CI
(c) 'CHFCF,C|
(D) CH,F'CFCI
END OF TEST
IF YOU FINISH BEFORE TIIVIE IS CALLED, CHECK YOUR WORI( ON THIS TEST.
qf;b.
PRINT your name on thc llnc bclow tnd rcturtr

thh booklct with'youF anrwcr shccL Flilurc to
rlo so mry rcsult in disquellficrtlon. r coDE 02212010
FORM TP 2015158 MAY/JUNE 20I5
CARIBBEAN EXAMTNATIONS COUNCIL
CARIBBEAN ADVANCED PROFICIENCY EXAMINATION@
CHEMISTRY - UNIT 2
Paper 01
I hour 30 minutes
09 JUNE 20t5 (p.m.)
l. Tlris test consists of 45 items. You will have I hour and 30 minutes to answer them.
2. ln addition to this test booklet, you should have an answer sheet and a data booklet.
3. Each item in this test has four suggested answers lettered (A), (B), (C), (D). Read each item
4. On your answer sheet, find the number which corresponds to your item and shade the space
fiaving the same letter as the answer you have chosen. Look at the sample item below.
Sample ltem r
Which of the fbllowing energy transitions is
the HICHEST in an organic compound? - Sample Answer
(A)
(B)
n to
o to o*
o* @oe@
(C) n to 7t*
(D) 7t to r*
The correct answer to this item is "o to o*", so (B) has been shaded.
5. lf you want to change your answer, erase it completely and fill in your new choice.
If
6. When you are told to begin, turn the page and work as quickly and as carefully as you can.
you cannot answer an item, go on to the next one. You may return to that item later.
d
9. You may use a silent, non-programmable calculator to answer items.
--5
DO NOT TURN THIS PAGE UNTIL YOU ARE TOLD TO DO SO.
il
-;{ Copyright O 201 3 Caribbean Examinations Council
il
I All rights reserved.
-.I
022t201O/cAPE 201 5
- -2-
Item I refers to the fbllowing structure. 5. Which of the fbllowing compounds will
NOT decolourize bromine water but will
6ft--NH2
ll\2-J Y decolourize potassium manganate(Vll) on
CHr
1
warming?
l. Based on the IUPAC rules, the name of the (A) Butane
compound above is (B) Ethanol
(C) Ethene
(A) l-phenylpropan-2-amine (D) Ethanoic acid
(B) l-benzylpropan-l-amine
(C) l -phenylbutan-2-amine
(D) l-phenylbutan- l -amine ltem 6 refers to the tbllowing information.
A substance reacts with
2. A hydrocarbon contains gT.gyocarbon and

l2'2yo hydrogen by mass' Its empirical
formula is
I. NaoH to form an ionic product
ll. H, in the presence of a nickel

tatalyst
(A) CH ,
(B) lll. ethanol to produce an organic
CH, comPound and water'
(C) CrH,
(D) CrH, 6. The substance with the properties above
could be
J. The equation for the formation of the o
anaesthetic, CFTCHBTCI, is ll
(A) CH,-C-H
cF.cH,cl Br:
> cFrcHBrcl.
The type of reaction occurring is (B)

tl
cH, _ c _ oH
(A) nucleophilic addition O


ll
(C) CH.: CH _ C _ OH
(D) CHt : CH - CH' - oH

4. In the reaction between ethene and bromine,
which of the following statements about the
reaction mechanism may be true?
l. A carbocation forms in the rate

determining step.
IL A dative covalent bond forms
between the bromide ion and
ethene.
lll. Heterolytic fission ofthe bromine-
(A) I only
(B) I and II orrly
(C) ll and III only
(D) l. ll and lll
CO ON TO THE NEXT PACE
022120t0/CAPE 2015
-3-
Item 7 re fers to the fbllowing incomplete 8. Diazonium salts are useful in the synthesis
of aromatic compounds. Which of the
q
equatron.
following compounds can be prepared from
a diazonium salt?
Lieht
+
CH = CHCHI
Br2 (g
(A) cooH
7. The product of the reaction above is

d
(B) cH2NH2
(A)
q*' d
CH = CIICIIT
(c)
dnon
(B) (D) OH
9t
H-C-C-CH3
ll
o
fH,
Br 9. A compound, X, reacts with

Br
I. 2, 4-dinitrophenylhydrazine
(DNPH) to give an orange
(c)
q"' ll.
precipitate
Tollen's reagent to give a silver
mirror
CH = CHCHr lll. aqueous alkaline iodine to give
yellow crystals.
(D)
q Brz
/8,,
CH=CH-C-H
-
Compound X is MOST likely
(A) cHr
\B" I
v
ffucno
(B) CH2COCr|3
I
1|F-sH
(C) cHr
4""(oH)cH!
{v
(D) CHzCOCH3
tftcro
\2
02212010/GAPE 20l 5
-4-
lo. Which of the carbon atoms (indicated by an arrow and labelled (A), (B), (C), and (D)) in the
tbllowing molecule is the MOST tikely site tbr nucleophilic substitution to occur'l
HO
c-. (D)
rAl
'\,, cII, Br
1cr--=PcHt '. '; .
(B)
-(A)
ll. 2-hydroxy-2-methylpropanoic acid can be formed from propanone in two steps as illustrated below.
cHr
C=O
frI3 f"' c\,,o
cHr
CHr
-C-C=N cH3
-f -
OH OH OH
I. Step X involves nucleophilic addition.
II. Aqueous potassium cyanide is the reagent in Step X.
IIl. Step Y involves hydrolysis.
(A) I only
(B) I and II only
(C) ll and III only
(D) l, II and III
Item 12 refers to the following conversion.
-
.cH2cH3
'+ctz cHzcH3cl
q d +Hcr
-'
t2. Which reaction mechanism occurs in the conversion?
(A) Electrophilic addition
(B) Electrophilic substitution
(C) Free radical substitution
(D) Nucleophilic addition
CO ON TO THE NEXT PACE
022t20 t0/CAPE 20 r5
-5-
13. Which of the following statements is NOT 16. Which of the fbllowing factors will NOT
trueof addition polymerization? af'fect the accuracy of the results in a
titrimetric analysis?
(A) Only one type of polymer is
formed. (A) Purity of reagents
(B) hydrolysed
The polymer is readily (B) Adding excess water to the conical
to the monomer. flask
(C) Tlremolecularmassofthepolymer (C) Blowing the reagent out of the

is a multiple of the monomer pipette tip
unit. (D) Overshooting the calibration mark
(D) The physical and chemical of the volumetric flask
properties of the polymer are
different from those of the
monomer. 17. Species which absorb light in the UV-Vis

region have
14. Which of the following compounds I. saturated bonds
will form an aqueous solution with the II. unsaturated bonds
HIGHEST pH? lll. non-bonded electron pairs.
(A) C(CHr)3 OH (A) I only

(B) Cq C(OH) (CHr), (B) I and II only
(C) CH3 CH(OH) Cq (C) II and lll only
(D) CH3 CH" CHr OH (D) I, II and III
15. What would be OBSERVED when 18. UV-Vis molecular absorption arises from
aqueous bromine is added to the following vibrational and rotational hansitions from
compound?
I. within the ground state
OH II. the ground state to the excited state
- IIl. the excited state to the ground state.
(A) I only
(A) reaction.
There is no visible (B) II only
(B) The colour of the bromine is (C) I and ll only
d ischarged and a wh ite (D) ll and lll only
precipitate is formed.
(C) The colour of the bromine is
discharged leaving a yellow

precipitate.
(D) The colour of the bromine is
discharged and a colourless
solution is formed.
022t20 tO/cAtr6 201 5
-6-
Items l9-20 ret'er to the fbllowing 22. A compound absorbs light of frequency
infbrmation . 940 MHz. The wavelength, in cm, of the
light absorbed is (c : 3.0 x 108 m s-')
A student carries out the gravimetric

analysis of a soil sample taken fiom an (A)
31.91
area surrounding a garage. The soil sample (B) 31.91 x l0-,
is found to be contaminated with pb2*
(C) 31.91 x l0-'

ions. I 00 cmr of a solution obtained from (D) 3 L9l x l0{
the sample when mixed with 25 cm3 of
0.100 moldma HClyields 0.010 g of lead
chloride- 23. Which of the fbllowing relationships is
TRUE for the absorbance, A, of UV-Vis
[The relative formula mass of lead chloride light by a solution of concentration c?

is278.2.1
(A) A = €cl
19. The balanced equation for the reaction (B) A=cllE
between lead ions and hydrochloric acid is

iCl A = c/fl
(D) A = tc/l
(A) Pb (s) + zHCl (aq) -+ pbCt, (s)
+ H, (g)
24. Which of the following regions of the
(B) 2Pb (s) + 2HCl (aq) -+ 2pbCl (s) electromagnetic spectrum BEST matches
+ Hr (g) the wavelength ranges of B e and R?
(C) Pb2* (aq) + 2HCl (aq) -+ PbCl" (aq) Frequency (Hz)

+ 2H.(aq)
(D) Pb2*(aq) +2HCt (aq) + pbCt,(s)
+ 2H*(aq)
PaR
20. What is the concentration of pb2* in the

PAR
original solution? - (A) UV IR radio
(B) lR UV radio
(A) 3.60 x l0-5 moldm-3 (C) lR UV x-rays
(B) 3.60 x l0-{ moldm-3 (D) UV tR x-rays
(C) 5.40 x l0-+ moldm-3

(D) 7.20 x l0-a mol dm-3
21. Which of the following materials are
commonly used stationary phases in

chromatography?
(A) Cellulose, alumina, lime
(B) Alumina, cellulose, silica gel
(C) Lime, silica gel, cellulose
(D) Silica gel, lime, alumina
CO ON TO TI_IE NEXT PAGE

022t20loicAPE 2015
7-
t< Which of the fbllowing processes occur in Which ofthe following compounds are the
29.
a massspectrometer before isotopes can be MAIN impurities in bauxite?

detected?
I. lron(lll) oxide
I. Acceleration II. Lead oxide
It. Amplification III. Silicon(IV) oxide
III. Deflection lv. Calcium carbonate
(A) I and II only (A) I and III only
(B) I and lll only (B) I and IV only
(c) Il and llI only (c) II and III only
(D) I, II and lll (D) II and [V only
26. A mixture of gases containing methanol, 30. Compound X contains three components
P, Q and R. Component P is needed as

ethanol, propan- I -ol and propan-2-ol, was
obtained from a refinery. What method can the starting material for the synthesis of a
be used to separate these gases for analysis? new drug, Which ofthe following methods
of chromatography is MOST suitable for
(A) Mass spectroscopy obtaining a pure sample of Component P?
(B) IR spectroscopy
(C) Gas-liquid chromatography (A) Column
(D) High pressure liquid chroma- (B) Paper
tography (C) Gas-liquid
(D) Thin layer
27. What transitions are expected from

C6H5NO" in a UV-Vis spectrum? 31. Which,of the following processes is NOT'
involved in the manufacture of ethanol?
(A) n -+ n'and n -+ o'
(B) n r o'and o-+o'and n *7t' (A) Fermentation
(C) n
- rt' and n
-z' and n --r o* (B) Aerobic oxidation of sugar
(D) fi - tu'and n -* n* and o --- o' (C) Catalytic hydration of ethene
(D) Biological catalysts - enzymes
28. Which of the following species is NOT
a significant fragment from the mass
spectrum of ethanol?
(A) OH*
(B) CHr*
(c) crHr*
(D) C,H5OH*

022t20 tO/CAPE 20 | 5
8-
'fhe chlor-alkali industrv is

32. 36. The FDA regulates the use of food additives
and requires that additives NOT be used
I. a redox process
lt. an electrolytic process L to disguise faulty or inferior
ilt. necessary in making bleach. products
ll. to enhance the colour and llavour
(A) | and ll only of fbod products

(B) | and lll only lll. when they significantly destroy
(C) ll and lll only nutrients.
(D) I. ll and lll
(A) I only
(B) ll only
J3. Which of the following occurrences may (C) I and ll only
be a result of a light-induced reaction of (D) I and lll only

pollutants in the air?
l. Globalwarming 37. Flocculation is a process involved in the
ll. Photochemical smog
lll. Greenhouse effect (A) clarification of water
(B) cleaning of the f'umes in the Haber

(A) lonly Process
(B) ll only (C) conversion ofexcess SO, gas in the
(C) I and lll only contact process into MgSOn
(D) I, Il and lll (D) production of ethanol by
fermentation
34. Fermentation of sugars to alcohol is
controlled by an enzyme complex (mixture) 38. Chlorine is the active component fbr
known as swimming pool disinfectants, although it
is a poisonous gas.
(A) lipase
(B) zymase
(C) sucrase
Which of the following salts is used as a
(D) amylase
safe chlorine source?
(A) HCIO
(B) CaCl,
35. During an earthquake. household water

(C) NaClo
supply is MOST likely to become polluted
(D ) NaClO,
by
(A) broken sewage mains entering the
J9. ln which layer of the atmosphere is

water supply
ozone detrimental to human health and
(B) landslides occurring in the vegetation?
watershed areas
(c) dumping of industrial waste into
rivers and streams

(A) Mesosphere
(D) drainage of chemical f'ertiliser and

(B) Thermosphere
pesticides into the soil

(C) Troposphere
(D) Stratosphere
CO ON TO'fHE NEXT PACE
022t20loicAPE 201 5
10. Which of the following outcomes are 12. The appearance of a bright red precipitate
advantages of using incineration as atbrm on the addition of Fe(NOr), to a sample of
of solid waste disposal? water indicates the presence of
t. Pathogens are destroyed in the (A) Noi

. process. (B) cN-
II. Incineration reduces the volume ot, (c) Por'-
.solid waste. (D) SCN-'
III. Heat produced can be used to
generate electricity.
43. Chlorofl uorocarbons undergo homolytic

(A) I and II only fission by being exposed to ultraviolet light
(B) I and III only in the stratosphere.
(c) ll and lll only
(D) I, ll and III Which radical could result from
cH,FCF,Cl?
41. Chlorine can be produced by the diaphragm (A) 'CH,CF,CI

nlethod and mercury cell electrolysis.
Which ofthe following statements are true

(B) CH,FCF,'
regarding the diaphragm cell method? (c) 'cHFcF,cl
(D) CH,F.CFCI
t. It is less energy etfrcient.
II. It is more energy efficient.

III. It is less harmfultothe environment.
44. A sample of crude oil contains mainly
CrH,r. In which crude oil fraction would

(A) I and II only you expect to find this sample?
(B) I and III only
(c) II and III only (A) Bitumen only
(D) I, ll and lll (B) Kerosene and bitumen
(C) Naptha and gasoline
(D) Refinery gas
45. Thermal pollution results in
(A) increased fi sh population
(B) no change in dissolved oxygen
(c) less dissolved oxygen in water

(D) tnore dissolved oxygen in water
END OF TEST
IF YOU FINISH BEFORE TIME IS CALLED. CIIECK YOUR WORK ON THIS TEST.
02?t20 rO/GAPE 20l 5
a r coDE 02212010
FORM TP 201.6I.68 MAY/JI.JNE 2016
CARIBBEA}I ADVAI{CED PROT'ICIENCT EXAMINATIONO
CHEMISTRY
IINfT2-Paper0l
7 hoar 30 minuta
07 JUNE 2015 (p.m)
READ THE FOLLOWING INSTRUCTIONS CAREFTTLLY.
l. This test consists of 45 items- You will have I hour and 30 minutes to answer them.
2- In addition to this test bookleq you should have an answer sheet and a data booklet.
3- Each item in this test has four suggested answers lettered (A), (B), (C), (D). Read each item
you ar.e about to answer and decide which choice is best.
4. 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.
Sample Item
Which of the following enerry transitions is
the HIGHEST in an organic compound? SamoleAnswer
(A)
(B)
ntoo+
otoo*
@o o@
(c) ntor*
(D) 7t to r*
The correct answer to this item is "o to o*., so (B) has been shaded-
5. If you want to change your answer, enase it completely and fill in your new choice.
6- When you are told to begin, turn the page and work as quickly and as carefully as you can. If
you cannot answer an item, go on to the next one. You may return to that item later.
7- You may do any rough work in this booklet.
9. You may use a silen! non-pnogrammable calculator to answer items.
-
I
-r
I DO NOT TURN THIS PAGE I'NTIL YOU ARE TOLD TO DO SO.
Copyright @ 2Ol4 Caribbean Examinations Council
-lr
-I All rights reserved.
- 022t20t0tcAPE 2016
-2-
I Combustion analysis of 0.18 g of an f,. Which of the following statements about
organic compound produces 0.396 g of - polyunsaturated oils (trigylcerides) is

carbon dioxide and0.2l6 g of water. The FALSE?
empirical formula of the compound, given
that it contains carbon, hydrogen and (A) They undergo saponifi caton.
oxygen only, is (B) They are hydiolyzed to produce
diglycerides.
(A) C,HP (c) Theirshelf lives arc prolonged with
(B) CoHrO hydrogenation.

(D) They are hydrogenated to produce
(c) c,HrQ margarine.
(D) C6H,P,
An alcohol is tneated with acidified IlCrrO,
6.
2- Which of the following compounds show and the resulting mixture gives a positive
optical activity? tri-iodoform test. Which of the following
structures BEST represents the alcohol
I. CH3CH(OH) COOH used?
II. HOCH: CHOH

(A) CE3- OE
III. CH3CH (Cl) CH3
ry. HC @r) I Cl
.E
(A) I and II only (B) cu3- c

I
(B) I and IV only -cE3

(C) II and III only I
(D) III and IV only

OH
EII
3. Pentane has the molecular formula CrH,r.

How many possible isomers does thil (c) cE3- c
ll
compound have? tt
-c-E
EOE
(A) I
(B) 2 cE3
(c) 3 I
(D) 4 (D) cEr- c
I
-(Er
OE
4 Which of the following compounds is
hydrolyzed by water?
(A) CTH5OH
(B) C5H5COOH
(c) c6H5cHrCl
(D) -@-cHpl a

o22t20l0tcAPE 2016

-3-

Item 7 rcfers to the following reaction for the conversion of Compound R to Compound Y.

Nou

Reagmt

, E,€_ NE,

Noz
CompoundR CompoundY

7. Which of the following reagents can be used to convert Compound Rto Compound Y?

(A) NaOH
(B) LiAl4

(c) N4oH

(D) Sn/conc. HCI

8. Which of the following equations is correct for the reaction of 4-methyl phenol with ethanoyl

chloride?

cocE3

(A) +CEsCOCI +HCl

---;'

OE OE

(B) +cHrcocl +ECt

OE ooccE3

(c) + cE3cocl +cq cl

-->
OH OE

(D) +cqcoct + cE3 cooE
--+

OE CI a

022t20totcAPE 2016

-4-
Item,9 refers to the comPounds, B Q, R Item 11 refers to the three amines, X, Y and
and S, with the following structures- 7-with the following formulae.
a P: CH3(CH2)4CHrOH X: CH,CI CHCINH2
Q: CH3(C[{r)3CI{TCOOH Y: CH3CH2NH2
R: CH,(CIL)3CHCICOOH c6H5cH2NH2
S: C.HpH
ll Which ofthe following sets of pH values
is LIKELY to be for the amines, X, Y and
Z respectively?
9. The correct sequence of the compoundq in
order of DECREASING acid srength, is
XYZ
(A) BS,Q,R (A) 7.7 9.8 8.5
(B) Q,&S,P (B) 9.8 8.9 7.7
(C) BQ,S,P (c) 9.5 13.0 9.0

(D) S,B"qP
(D) I 3.0 10.0 9-0
10. Which of the following compounds does
NOT give a white precipitate when shaken

cEr
(A)
cl
CI
(B) cE2cl
+CI
cHc12
(c)
(D)
cEcl2
GO ON TO THE NEXTPAGE
0zzr2.OtOlCAPE 2016
-5-
12. The halogenoalkane (CHJ3CX (X : halogen) when treated with aqueous sodium hydroxide
undergoes a substitution reaction. Which ofthe following reaction sequences shows the mechanism
for this reaction?
C}L CH,
a
9H,
\,/
cH_
t'
(A) Ho
^"t4.
",{ lr,
-*
H-O----C
I
I
cHr
---- X -€ -H<)- c
cH3
I
-CH,
+ X-
CH. CH, CH3 cH-
o+. l' \,/ I'
(B) Ho
H3c
./ v*cH3
-+ H-O---- C
CH,
---- X
-+ HO
-C-CH,
I
cHr
+ )f
i'' x cH3 cH!
(c)
-+ cH.-l*4,
I
cH, c -+ cH3- c If
I
\-/ I
-OH +
I
CH, CH, CH,
(D) cH,
i"
c cHr- c
cHr
I
*fr"
cH3
I
c )f
-OH +
CH,
I -> I -) I
CH, cHr cH3
13. Phenol and benzoic acid can be distinguished by their reaction with
(A) Na(s)
(B) NaCl (aq)
(C) NaOH(aq)
(D) NqcQ (aq)
14. which of the following statements is Nor true of addition polymerization?
(A) Only one type of polymer is formed-
(B) The molecular mass of the polymer is a multipre of the monomer uniL
(c) The polymer is readily hydrolyzed to the monomer-

(D) The physical and chemical properties of the polymer are different from those of the
monomer.

o22t20t0tcAPE 2016
-6-
Item lP refers to the following repeat unit Item 18 refers to the following apparatus
of some polymers. used in organic preparations-
o
a
lt
_N
-C_
15- Which ofthe following polymers have the
repeat unit shown above?
I. Amino acid Heat
II. Nyton
m. Polyamide 18. For which of the following processes is the
apparatus NOT suiable?
(A) I and tI only I
(B) I and III only (A) Conversion of phenylamine to :
(C) II and III only benzenediazonium ch loride
(D) I,II and III (B) Conversion of butan-l-ol to
I - bromobuane
(c) Oxidation of propan-2-ol to l
t6. Which of the following statements is pnopanone
NOT true about the detection limit of an (D) Oxidation ofmethanol to methanoic
instrument? acid
(A) It is related to the sensitivity.
(B) It is equal to the standarddeviation. 19. Which of the following inaccuracies may
(c) It is usually expressed h parts per be eliminated by calibrating a measurin!
million. instrument?
(D) It is the lowest concentration ofan
analyte that can be detected- (A) Lack of precision

(B) Random errors
17, The concentration ofan ammonia solution (C) Systematic errors
is determined by titratin 925.0 cm3 against (D) Random and systematic errors
0.2 mol dm-3 sulfuric acid to give an end
pintof 27.5 cm3.
The concentration of ammonia
(in molO.-r1 is given by
(A) 0.2x 27.5
25
(B)
O.2 x 27.5
2x25
(c) 2x0.2x27.5
25
2x 02 x25
(D)
27.5
022120l0tcAPE20t6
i
I
-7-
;
20. In an electronic transition in the UV/visible 23. An unknown organic compound with
region of the spectnrm, a wavelength of molecular mass of 44 g is analyzed using

450 nm is absorbed. infrared radiation- The bonds are found at
17@ cmr and 2800 cm'r.
a
Planck constant (h) : 6.09 x I Or J s
Velocity of light (c): 3.00 x 108 m sr The compound is MOST likely
The enerry ofthe corresponding photon (A) ethanal
(in Joules) is (B) ethanol
(c) ethanoic acid
(A)
6.3x lO-n xlOt (D) carbon dioxide
4.50 x l0-5
(B)
4.50x l0-7
24 Which of the following analytical
6.63x l0-!x3xl08
techniques is considered MOST specific
6.63x l0-3n x3xlOt for identifi cation purposes?

(c)
4.50x104
(D)
6.63x l0-s x3xl08 (A) Mass spechoscopy
4.50 x l0-7 (B) LI"VNIS spectnoscopy
(C) Gas chromatography

(D) Thin-layer chrornatography
2t Which ofthe following setsofregions inthe
electromagnetic spectrum is in the correct
order of INCREASING wavelength?

25. Which of the following pairs of compounds
do NOT absorb infrared radiation?
(A) UV VIS X-ray IR

I. H, and Cl,
(B) X-ray UV VIS IR

(c) VIS UV IR X-ray
II- NH, and HCI
(D) IR VIS UV X-ray

III. N, and Br,
(A) I and II only

(B) I and III only
22 Which ofthe following types ofelectronic

(C) II and III only
transitions would NOT produce absorption
(D) I,II and III

in the UVA/IS region of the spectrum?
(A) s-*P* 26. lnfrared spectroscopy is widely used to
(B) p- p* monitor atmospheric pollutants. Which
(c) n*p* of the following atmospheric pollutants
(D) n+s* is NOT usually monitored by infrared
spectroscopy?
(A) 03
(B) CO,
(c) NO,
(D) SO,
022l20t0tcAPE 2016
i
J
-8-
Item 27 refers to the following mass spectrum that was obtained from Compound R which contains
the elements carbon, hydrogen and nitroge-n.
sM0
a Iltersity sw 100
AM1
100
75
5C
tp
0 lc 20 30 40 50 a 70 80 90 100
m/z value
27. How many carbon atoms has Compound R?
(A) I
(B) 3
(c) 6
(D)7,
Item 28 refers to the following diagram showing a chromatogram obtained from separating the
components of a dye by paper chromatography.
G- c
G- B
o- A
o...- Oddnalpmitionof dye
2E. In the chromatographic experiment, the mobile phase used was tetrachloromethane. Which ofthe
following statements are true?
I. ComponentA is most soluble in the mobile phase.
II. ComponentA is most soluble in the stationary phase-
III. Component B is more polar than Component C.
IV. Component C is the most polarof the components.
(A) I and II only
(B) I and IV only
(c) II and III only
(D) II and IV only
0221201O/CAPE 2016
-9-
29. Which ofthe following diagrams shows the boiling point-composition curve for a minimum boiling
point azootrope for a mixture ofA and B?
(A)
a
(B)
PureA PureB PureA PureB
(c) (D)
A
ca o
50
lL
E!
trl no
PnreA PureB PureA PureB
30 Which of the following features are 31 The extraction of aluminium is an
advantages of steam distillation? electrolytic process where the electrolyte

used is purified ore dissolved in cryolite,
I. It occurs under reduced pressure- NarAIF..
II. The components do not decompose.
nI. It provides savings in fuel cost. Which ofthe followingdescriptions is true
forthe use of cryolite?
(A) I and II only
(B) I and III only (A) Providing an additional source of

(C) II and III only aluminium
(D) I, II and III (B) Reducing the mehing point of the
mixture
(C) Increasing the electrical
conductivity of the melt
(D) Providing an addititional source

of aluminium and reducing the
melting point of the mixture

o22t20l0tcAPE 2016
t'
i
-l0- I
32. Which of the following substances are the 36. Which of the following products is NOT
MAIN impurities in bauxite? produced for commercial purposes by the
electrolysis of concentrated brine?
a I. lron(Il) oxide
II. Calcium oxide T (A) Oxygen
I[- Silicon(IV) oxide (B) Chlorine
(c) Hydrogen
(A) I and II only (D) Sodium chlorate(V)
(B) I and III only

(C) II and III only
(D) I, II and III 37 Compounds of sulfur such as sulfites are
used as food additives because they
33. Chlorofluorocarbons undergo homolyic (A) improve the flavour of food
fission by beingexposed to ultraviolet light (B) help to enhance the colour of food
in the stratosphere. (C) inhibitthe oxidation of unsaturated
fats
Which radical could result from (D) help to preserve the food by
cH,FCF2Cl? dehydration
(A) CH2F'CF'
(B) 'C4CF,CI 38. Chlorine is the active component for
(c) 'CHFCF2CI swimming pool disinfectane, although it
(D) CH2F'CFCI is a poisonous gas. Which ofthe following
salts is used as a safe chlorine source?
34. The essential conditions for the Haber (A) HClo
process are
(B) CaCl,
(A) 2 atm pressure,400 oC, iron catalyst
(B) 2 atn pressure, 450 oC, no catalyst (C) NaClo

(C) 200 atm pressure, 450 "C, iron
(D)
catalyst
200 atm pressure, 1000 "C, no
(D ) NaCIQ
catalyst
39. Which ofthe following chemicals are added
35. Which of the following environmental

to the final product water in the desalination
post-treaunent stage?
problems could be caused by the incomplete
combustion of ethanol in a car engine? I. Lime (Ca(OH)r)
II. Iron(III) chloride
(A) Global warming III. Sodium hypochlorite (NaOCl)

(B) Ozone depletion
(C) Greenhouse effect (A) I and II only
(D) Photochemical smog (B) I and III only
(C) II and III only
(D) I,II and III
022t20t0tcAPE2016
-il-
Item 40 refers to the following schematic 41. In which layer of the atnosphere does
diagram. ozone act as a pollutant?
Rain and (A) Troposphere

a N,
fixafion Iighbirg (B) Mesosphere
x 1
(C) Statosphere
bacteria (D) Thermosphere

basteria
Organic Plan& 42. Which of the following resources are
w N, Y normally associated with the formation of
compounds photochemical smog?
Bacteria Bacteria I.
z Nitrogen oxides
II. Sunlight
ilI. Volatile organic resources
(A) I and II only

(A) nitrate (B) I and lll only
(B) nitrites (C) II and III only
(c) nitric(V) acid (D) I,II and III
(D) ammonium salts
43. Which ofthe following compounds
is NOT
a primary pollutant?
(A) Nitrogen dioxide
(B) Carbon monoxide
(c) Nitrogen monoxide

(D) Sulfur dioxide
022t20t0tcAPE 2016
r
!
-12-
Item 44 refers to the following graph which shows the concentration (ppmv) of various atnospheric
pollutints at various times throughout amoming.
05
* 0.4
€os Aldchyde.s-
ql
L
Nihogen dioxide
t
E0,
ao o.t
4 &nL 6
'.IIL
t t-m. 10 a-m. t2 EJTL 2 l.rn- 4 a-lll, 6 e-tn.
44. It can be concluded from the graph that
I. aldehydes and ozone are secondary pollutans
II. hydrocarbons are secondary pollutants
III. nitrogen monoxide is a primary pollutant
(A) I only
(B) III only

(C) I and III only
(D) II and III only
45. Which ofthe following substances is a MAJOR component of biomass?
(A) oil
(B) Ethanol
(c) Cellulose
(D) Natural gas
END OF TEST
rF you FrMsH BEI'ORE TrME IS CALLED, CHECK YOUR WORr( ON TmS TEST.
022t20t0lcAPE 2016
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·- + AFFIX SEAL HERE +

CARIBBEAN EXAMINATIONS COUNCIL

READ THE FOLLOWING DIRECTIONS CAREFULLY

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

about to answer and decide which choice is best.

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

(A) n to er• Sample Answer

(C) CJ 'tO CJ*

4. Ifyou wanttochangeyouranswer, besuretoeraseyouroldanswercompletely and fill in your new

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.

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

1. Volatility of organic compounds depends on .llim_1 refers to the following structure.

present. Which compound below would be

the MOST volatile? H H H H

(A) CH,CH,CH,OH H-C-C-C-C-H

(B) CH,CH 2 CH 2CH, I I I

i. The IUPAC name for the structure is

(A) 2 - ethyl butane

(B) 3 - ethyl butane

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

{A) CH3 -C-OH · HO-C-CH,

{D) H-C-C-OH HO-C-C-CH3

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

!.CY The polymer is readily hydrolysed to the monomer.

(D) The physical and chemical proJlerties of the polymer

are different from those of monomer.

to the addition polymer represented by the

5. The monomers are MOST likely

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

(HOOC -@--coOR). by complexing it with Pd2+ catalyst in the

Which ofthe following characteristics would

terylene MOST likely possess?

(A) It has the same empirical formula as

(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.

electron density in the double bond.

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

(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

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