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
sample item below.
having the san1e letter as the answer you have chosen . Look at the
Sampl e Iten1
···.!.
··s·

_1~ Which of the follow ing is the HIGHEST energy transiti on in an organic
con1pound?

(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 ~f
6. When you are told to begin, tum the page and work as quickly and
to this item later. Your sc 1 .
you cannot answer an iten1, go on ~o the next one. You n1ay return
will be the total nmnbe r of correct answer s.
7. You tnay do any rough work in this bookle t.
Figure s are not necess arily drawn to scale.

-===
8.
...
_ _J
9. 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

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Copyr ight© 2010 Caribb ean Examin ations Counci l
=
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All rightsr eserve d.
 l
-2- I
!

1. Which statement is true about C - C bonds? 3. The compound which shows both ci - rans
----,
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'\ H
"I c C- H

r
'\
H
I
!
H H
in single bonds than in double H
bonds. I
I
(D) Single bonds are more reactive
I
towards most reagents than Cl
Cl
double bonds.
'\ / l
(B) c= c 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
. (C)
(D)
2 - methyl pentane
3 - methyl pentane (D)

c
"
/
c c
I

"
/j"-
H 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) ~H1 0H

(B) CH 3CH2CH2CH3
I:::~ (C) CH 3CH(CH3 )CH 3
(D) CH3CH2CH2COOH
CH1 0H

l (B)
I
5. In the reaction between ethene and CH- C - H
bron1ine, which statemen ts about the 3 I
reaction mechanism are true?
l I. A carbocatio n 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-
bromine bond occurs.
CH 3

CH 3
l_ (A)
(B)
I and II only
I and III only I
(C) II and III only (D) CH- C - OH
(D) I, II and III I
L 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

(B) free radical substitution
(C) nuc.Ieophilic addition
(D) nucleophilic substitution

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)

The mechanism used is

(A) eJectrophilic addition

Cl
(B) nucleophilic addition
(C) electrophilic substitution
(D) nucleophilic substitution (B)

I
i
Iten1 9 refers to folJowing diagram of i
I
Compound A. CJ I
(C)
0 I
I
I
II
(D) i

nc==cn2 I
I
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 silv~r 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
(C) II and JII only i
(D) I., II and HI (A) ethanal is more susceptible Ito
e)ectrophilic attack than et ~:~i,1e
(B) ethan~ I is more susceptible t tl' jee
rsd1caf attack than ethene 1

(C) ethanal is more susceptib ito

nucleophilic attack than et et~e
(0) the addition product formed '- ~th
ethene would be unstable

I
GO ON TO THE NEXT PA ~.
I .......
-l J~fl~J1?·''

1;1 - 5-
::;i~~ . Jten1 13 refers to the following structure of 16.
I
Which of the following may be elimi ~fed
tyrosine. by calibrating a measuring instrume t I

(A) Lack of precision

(B) Random en-ors
(C) Systematic errors
(D) Random and systematic erro s

1\~
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
(B) The 1nolecular mass of the polymer (C) Overshooting the calibration
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
(B) Gravimetric analysis never orbitals
involves the removal of volatile (B) large difference in energy b
components of a solid~ the bonding and non-b
(C) The analyte can be identified after orbitals
precipitation and isolation have (C) small difference in energy b
occurred. the bonding and non-b
(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
fi~equency 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

GO ON TO THE NEXT PA
-...,
 -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 s~re.
l (B)
(C)
Cellulo se
Silica gel
II.
Ill.
The compon ents do not deco 1~ose.
It provid es savings 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
..I
. (D) I, 11 and III
j 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 followi ng results: 31. Which of the following are important l~ors
to conside r in detenni ning the locati 1 ?f a
Compo und Distan ce Travel led factory? i
I
(em)
Compo und A 1.5 I. Prox~mity.t~ a potential work o~:ce
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
(A) I, II and III only
(B) 0.12
(B) I, II and IV only
(C) 0.16
(C) I, Ill and IV only
(D) 0.73
(D) I, II, III and IV

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
impurities of bauxite?
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-

37. In the elec troly sis of brin e u ing the·

Item 33 refers to the follo wing fractions of
crud e oil. diap hrag m cell, two by-p rodu c s re

I. Dies el (A) chlo rine and oxyg en

II. Petrol (B) chlorine and sodium
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 prese nce 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
(D) IV, II, I, Ill 1

(C) pota ssium thioc yana te s J 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
.
e]ectroJysis of conc entra ted brine ? 39. C mnp oun ds o f· su lP.I1~r sue I1 .as. s~

are used as food addit ives. This 1 .ecause

1

they I
(A) Chlo rine
(B) Oxyg en I
(C) Hydr ogen (A) impr ove the flavo ur of ft i
(D) Sodi um chlor ate (V) (B) help to enha nce the colo ~f food
(C) inhib it the oxid ation ofun a: trated
fats
help to pres erve the by
In the Bosc h-Ha ber proc ess, N., and H~ can
35. (D)
dehy drati on
be obta ined from X and Y respecti~eJy.
T
Whi ch of the follo wing pair s BES
desc ribes X and Y?
40. Whi ch of the follo wing use
y sulph uric acid'?
X
(A) Amm oniu m salts Naph tha I. Fet1ilizer
-
(B) Amm oniu m salts Air n. Paint
(C) Air Naph tha IIJ. Fibre
IV. Dete rgent
(D) Air Amm oniu m salts
(A) I. II and Ill only
(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 (D) L 11, JH and JV
consumption?

(A) Dige stion occu rs in the stom ach.

(B) Natu ral inhi bitio ns are re]ax ed
(redu ced) .
(C) Oxid ation occu rs in the bloo d.
(D) Reac tion time is redu ced.

GO ON TO THE NEX T P Cftf.

 -9-
. Item 44 refe rs to the follo wing 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 ~~--:-:R:-:-ai_n7a_n_d-tt--;r
(B) Car bon diox ide fixation ...-l lighJtnin g Li
!X
(C) Met han e Deni trifying J
(D) Wat er vap our bacteria Nitrifying

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

,
) bacteria

Organic Plants y
l
desc ripti on:
wr. .._D eca y.
f~~~r
N
2
4 I
J
i.i
compounds
n-11 ,
Aer oso l prop ella nts such as Freo I
use of Bacteria
CC13 F, are of 111ajor con cern beca
I
Bacteria ...
~
e,
thei r photochen1icaJ reac tion with ozon
ere
0 3 • Ultr avio let radi atio n in the strat osph
.ii,i·
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.

_~i
(A) nitrates
cal (B) nitrites
42. A bala nced equa tion for the pho toch emi
(C) nitri c(V) acid
deco n1po sitio n of Freo n- II is
(D) amm oniu m salts

J:l, ·:t.f•. t;;:.:·1

··;o-.:,-•·
(A}

(B)
CC13F(g)

CC13F(g)
hr ) 2Cl• (g) + CCI F•

hr > CCl •(g) + F•(g )

45. Wh ich of the foll owi ng plas tic
biod egra dabl e?
~~ re
:
3 .
1 Low dens ity poly ethe ne

J1t
(C) CC13 F(g) hf ) Cl•( g) + CCl F•(g ) (A)
2
(B) Poly then e tere phth alate . 1

'l'i~t··· hr ) 3Cl• (g) + CF• (g) (C) Po1y (3 - hydr oxyb utan o1c ac dO

-·I
_j ·. 43.
(D) CC13F(g)

A bala nced equa tion for the prod ucti

from ozo ne is
on of
(D) Poly viny lchl orid e I
i

oxy gen

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

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

END OF TES T

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

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n1 ntr " nu " l n l "l