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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.)

READ THE FOLLOWING INSTRUCTIONS CAREFULLY.

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
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
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.

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.

8. Figures are not necessarily drawn to scale.


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 I. NaoH to form an ionic product
formula is
ll. H, in the presence of a nickel
tatalyst
(A) CH ,
lll. ethanol to produce an organic
(B) 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. o
The type of reaction occurring is (B)
tl
cH, _ c _ oH
(A) nucleophilic addition O
(B) free radical substitution ll
(C) electrophilic substitution (C) CH.: CH _ C _ OH
(D) nucleophilic substitution

(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-
bromine bond occurs.

(A) I only
(B) I and II orrly
(C) ll and III only
(D) l. ll and lll
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022120t0/CAPE 2015
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Item 7 re fers to the fbllowing incomplete 8. Diazonium salts are useful in the synthesis
equatron. of aromatic compounds. Which of the

q CH = CHCHI
+ Br2 (g
Lieht
following compounds can be prepared from
a diazonium salt?

(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 Br
9. A compound, X, reacts with

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
I
\B"
v
ffucno
(B) CH2COCr|3
I
1|F-sH
v
(C) cHr

4""(oH)cH!
{v
(D) CHzCOCH3
I

tftcro
\2
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02212010/GAPE 20l 5
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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)
I

rAl

1cr--=PcHt '\,,
'.
cII, Br
'; .

(B)
-(A)

ll. 2-hydroxy-2-methylpropanoic acid can be formed from propanone in two steps as illustrated below.

cHr
C=O CHr
frI3 f"' c\,,o
cHr
-C-C=N cH3
-f -
OH OH OH

Which of the following statements about these steps may be true?

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

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022t20 t0/CAPE 20 r5
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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.

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022t20 tO/cAtr6 201 5
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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)


PaR
+ 2H*(aq)

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

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022t20loicAPE 2015
7-
t< Which of the fbllowing processes occur in 29. Which ofthe following compounds are the
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
ethanol, propan- I -ol and propan-2-ol, was P, Q and R. Component P is needed as
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*

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022t20 tO/CAPE 20 | 5
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32.
'fhe chlor-alkali industrv is 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
Which of the following salts is used as a
(C) sucrase
safe chlorine source?
(D) amylase
(A) HCIO
35. During an earthquake. household water
(B) CaCl,
supply is MOST likely to become polluted
(C) NaClo
(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

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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