a r coDE 02212010

FORM TP 201.6I.68 MAY/JI.JNE 2016

CARIBBEAN EXAMINATIONS COUNCIL
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.

8. Figures are not necessarily drawn to scale.

9. You may use a silen! non-pnogrammable calculator to answer items.

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I

-r DO NOT TURN THIS PAGE I'NTIL YOU ARE TOLD TO DO SO.

I

Copyright @ 2Ol4 Caribbean Examinations Council

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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,

6. An alcohol is tneated with acidified IlCrrO,

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
OH
I

(D) III and IV only

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

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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 a
CI

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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
with cold ethanolic silver nitrate?

(A) cEr
cl

CI

(B) cE2cl

+CI

(c) cHc12

(D)

cEcl2

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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

cH3 cH!
i'' x
(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.

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Item lP refers to the following repeat unit Item 18 refers to the following apparatus
of some polymers. used in organic preparations-

a o
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 standard deviation. 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

(D)
2x 02 x25
27.5

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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
4.50x l0-7
(B) 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
25. Which of the following pairs of compounds
order of INCREASING wavelength?
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

22 Which ofthe following types ofelectronic
(B) I and III only
transitions would NOT produce absorption
(C) II and III only
in the UVA/IS region of the spectrum?
(D) I,II and III

(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,

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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
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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)
o
a

PureA PureB PureA PureB

(c) (D)
A
ca o
lL
50 E!

o
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

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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
to the final product water in the desalination
35. Which of the following environmental 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

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Item 40 refers to the following schematic 41. In which layer of the atnosphere does
diagram. ozone act as a pollutant?

a N,
Rain and (A) Troposphere
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
z Bacteria I. Nitrogen oxides
II. Sunlight
ilI. Volatile organic resources
40. W would MOST likely be
(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

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Item 44 refers to the following graph which shows the concentration (ppmv) of various atnospheric
pollutints at various times throughout amoming.

05
E
* 0.4

os
ql Aldchyde.s-
L
t Nihogen dioxide
E0,
ao o.t

0
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.

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