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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:Stbasfoursug gestedanswersl ettered(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 hav~ chosen. Look at the sample item below.

Sample Item

Wbichofthe following is the HIGHEST energy transition in an organic compound?

(A) n to cr* Sa.mpleAnswer

(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
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9.
10.
Figures_ are not necessarily dra\ltn to scale.
The use ofnon-program mable calculators is allowed.

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i iiiiii
DO NOT TURN THIS PAGE UNTIL YOU ARE TOLD TO DO SO.

- Copyright 2009 Carib beanExarninatio ns Council.

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All rights reserved.
iii.iii 0221201 O/CAPE2009
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5. A motorist suspects that his gasoline is
1. Volatility of organic compo11nds depends on
the strength of the intennolecu lar 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) Br2 (aq)
(A) CH3 CH2 C~OH
(B) ~(aq)
(B) C~CH 2 CH2 C~
(C) NaOH (aq)
(C) CP~CH(CH 3)CH3
(D) KMnO 4 (acidified)
(D) CH3 CH2 C:t~COOH

2. Combustion analysis ofO.l S g of an organic 6. In the reaction between the ethene and
bromine, which statements about the reaction
compound produces 0396 gofcarbon dioxide
mechanism. may be true?
and0.216 gofwater. The empirical formula
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 bromi~ ion and the
(B) C4H 1 0
carbocati.on.
(C) C 2H 1 0 4
m. Heterolytic fission of tb~ bromine-
(D) ~6HI60l bromine bond occurs.

(A) Ionly
3. The couect IUPAC name for the structural (B) I and ll only
formwa (C) !Iandillon ly
H CH3 CH3 (D) I, II and ill
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
(A) Lewis acid
(B) 2, 2, 4-trim.ethyl octane
(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. ~CH(OH) COOH
II. HOCH = CHOH .
m. ~CH (CI) c~
N. HC(Br)IC l .

(A) I and II only

(B) I and N only
(C) ll and m only
(D) .illandlVo nly.

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8. 2-hydroxy- 2 - methylpropan oic acid can be formed from p~opanone 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 ~S04 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?

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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 structu res below?
OH

t Q

70
R

@ lo~L I
H - C--7- 0
I
H

Positive inducti ve Conjug ative

(A) Negative inductive
effect effect
effect

Negati ve inducti ve Positive induct:i:ve --

(B) Conjugative
effect effect
effect
I
Conjug ative Positive inductive
(C) Negati ve :inductive
effect effect
effect

Conjugative Negati ve inductive

(D) Positive inductive
effect effect
effect

13. 'Which of the follow ing is NOT 1rue about 14. The repeating unit obtained from the addi:tion
condensation polymerisation? polymerisation ofthe mono~
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
The polym er has physic al and c1 a a a
(C)
chemical properties that differ from
the monomer units. H . H
(D) Small molecu les are elimin ated I I
during the condensation process. (B) -e-e-
l I
CI Cl

Cl H
I I
(C) -e-e-
l I
Cl H

Cl H Cl H
I I I I
(D) - c - c - c - c-
1 I I I
Cl H Cl H

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0221201 0/CAPE2009
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15. Which ofthe following is true for glucose and starch?

Starch Glucose

(A) High solubility in water High solubility in water

(B) Low soh~bility 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) Gravime~c analysis is a purely
(A) Burette quantitative method.
(B) Beaker (B) Gravimetric analysis never involves
(q Pipette therernovalofvohrtilecornpon~
(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
(D) Conductivitymeter 20. Treatment of a 10.00 g sample containing a
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
is given by (A)
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

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02212010/CAPE2009
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25. W'nich of the follow ing speci es is NOT a
21. \Vhich ofthe followingutilizesvibrations?
significant fragment from 1he mass spect rum
Radio wave of ethanol?
(A)
(B) Infrar ed
(C) UVN IS
(D) X-ray

22. The struc tural features whic h caus e

absor ption in the UVN IS regio n of the
as 26. In them_ass spect rome ter a molecular ion is
electroma~etic spect rum are know n
formed from a comp~und by
(A) crbonds
(A) "loss of a proto n
(B) chromoph(!res
(B) gain of~ electron
(C) isolated 1t bonds
(C) loss of an electron
(D)- lone pairs of electrons
(D) fragmentation ofthe compound

The co~lex ion [FeSC N) + has a mola r

2
23.
1 1 27. Which oftbe following is NOT a visualising
absorptivity (E) of7.0 x 10 (im3 mol- cm-
3
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
2cmcell,~
(C) N"mhydrin
(A) 3 X 1o-J mol dm-3 (D) t.ntraviolet light
(B) 6 x 1Q-3 mol dm.-3
(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 = 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.
steam disti11.a1ion?
(C) 29.4 Jlill
(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

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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
(A) !only ammoni a by the Haber Process is obtained
(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 influence location of (D) fractional distillation of crude oil
an industrial plant?

I. Proximity to housing schemes 35. Which of ~e followin g is NOT ne:essar y

n. Proximity to port for wine making?
m. Goodr~adnetwork
. 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
impurities of bauxite? system
IT. May cause liver disease
(A) Iron(II) oxide ill~ 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

I
\

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0221201 0/CAPE2 009
 - 8-
of
ine 40. The biolo gical oxyg en dem and (BOD)
Item 3 7 refers to the manufacture of chlor en
sis of brin e usin g the wate r meas ures the amo unt of oxyg
by the elec troly
diaph ragm cell. prese nt in a fixed volu me ofwate r
(A)
(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 mpos e orga nic matt er
(B) graphite
(D) prod uced by aqua tic plan ts in
(C) plati num with a coating of asbestos
photosynthesis
(D) titan ium with an inert coati ng of
ruthe nium (IV) oxide
t
41. Whi ch o~tb.e follo wing ions are signi fican
the contributors to eutrophication?
38. For the man ufac ture of whic h TWO of
follo wing indu stria l prod ucts is chlo rine
I. PO/ -
MOS~widelyused?

Solventl
II. No;
I.
II. Sodi um chloride
m. SOl -
m. Polyvinylchloride
rv. Cblorofl.uorocaxbons
IV. a-
(A) land II
(A) Iand llon ly
(B) land ill Iand illon ly
(B)
(C) Tian dill
(C) I, nan d m only
(D) llan diV I, II, m and IV
(D)

39. "Which of the follo wing indu strie s use A redu ction in the ozon e layer is believed
to
42.
sulphuric acid? caus ed by the actio n of
have been
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, illan dN

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

45. Which of the following plastics are

biodegradable ?

(A) Polythene terephthalate

(B) Low density polyethene
(C) Poly (3 - hydroxybutanoic acid)
(D) Polyvinylchloride

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0221201 O/CAPE2009