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FORM TP 2014152 MAY/JUNE 20I4
CARIBBEAN EXAMINATIONS COUNCIL
CARIBBEAN ADVANCED PROFICIBNCY EXAMINATION@
CHEMISTRY_ UNIT 2

Paper 0l
I hour 30 minutes
l0 JUNE 2014 (p.m.)

READ THE FOLLOWING INSTRUCTIONS CAREFULLY.

|. 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.
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.
7. You may do any rough work in this booklet.
8. Figures are not necessarily drawn to scale.
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
(D) C6H,P,
(B) | and lll onlY
(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

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 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)

d
cH2oH

(B) cHr-i-n I
HC
-
CH2

Compound J
I

OH
8. Which of the following statements are
correct concerning Compound J?
H
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

l. A carbocation forms in the

Q: CHr(CH,)3CH,COOH
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

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 4-

10. Which of the following compounds does ll. The complete reaction of phenol with
NOT give a white precipitate when shaken aqueous bromine is characterized by a
with cold ethanolic silver nitrate?
(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

I 12. Which ofthe following organic compounds

cl would release a proton MOST readily?

(c) cHct2 (A) cH3cH2oH

I
(B) cH3cooH
@ (c) c6H5oH

(D) (D) cH3oH

f+ct
o 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
,t

0-v rA H

o
I
H- c->cl
I
H

13. Which of the following options has the labels in the correct order to match the structures?

(A) Positive inductive Conjugative Negative inductive

effect effect effect
(B) Conjugative Negative inductive Positive inductive
effect etfect effect

(c) Negative inductive Conjugative Positive inductive

effect effect effect
(D) Negative inductive Positive inductive Conjugative
etTect efTect efTect

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 5-

14. Which ofthe following statements is NOT 18. ln gravimetric analysis of a substance
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.
unit. (B) Its composition would not have to
(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
15. The product formed by the polymerization is dissolved in water. The chloride is then
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
(B) Random erors (D) 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 s
0.2 mol dm-r sulfuric acid to eive an end
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
66.3x10-roxl08
0.2 x 27.5 (A)
(A) 4.50 x l0-5
25
0.2 x 27.5 4.50 x l0-7
(B) (B)
2x25 6.63 x lO-ra x 3 x 108

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-?

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 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'.*?

(A) (B) (c) t,o

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 1.5
(A) I and lll only 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
(A) Iodine
(D) 0.73

(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

GO ON TO THE NEXT PAGE

29. Which of the. following statements about 31. Along with silicon dioxide, which of the
the partition coefficient may be true? tbllowing compounds constitutes the main
impurities of bauxite?
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

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 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?

2SOr(g) + Oz(g) i v'o' 4'?0'c'

I. POnr-
'z "t\ 2SOr(g)
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.