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 .
1.
2.
3.
4.
then1.
This test consist s of 45 items. You will have 90 n1inutes to answer
a Data Bookle t.
In additio n to this test bookle t, you should have an answer sheet and
(C), (D). Read each · e
Each itetn in this test has four sugges ted answer s lettered (A), (B),
best.
is
you are about to answer and decide which choice
item and shade the s.
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~
con1pound?
Which of the follow ing is the HIGHEST energy transiti on in an organic
(A)
(B)
. (C)
(D)
.r
.·;
Satnple Answe r
n to a+
n ton:+
a to a*
1t
ton:*
been shaded.
The best answer to this iten1 is "a to cr*", so answer space (C) has
6.
your new choice.
If you want to change your answer , erase it comple tely and fill in
as careful1y as you can ~f
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.
8.
Figure s are not necess arily drawn to scale.
9.
You n1ay use a silent, non-pr ogranu nable calcula tor to answer iten1s.
5.
...
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--
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=
iiiiiiii
DO SO.
DO NOT TURN THIS PAGE UNTIL YOU ARE TOLD TO
Copyr ight© 2010 Caribb ean Examin ations Counci l
All rightsr eserve d.
l
I
-2-
1.
Which statement is true about C - C bonds?
A double bond is made of a sigma
bond and a pi bond.
There is a higher electron density
between the atoms in a single
bond than in a double bond.
The distance between the nuclei
of the carbon atoms is shorter
in single bonds than in double
bonds.
Single bonds are more reactive
towards most reagents than
double bonds.
(A)
(B)
(C)
(D)
!
3.
The compound which shows both ci - rans
isomerism and optical isomerism is
H
H
"I
c
(A)
H
c
/I'\
I
I I I
I
I
/
c
"I
H
c
I
'\
c= c
!
c
IJ"- H
l
"
/
H
/
I
c
I
--,
/
H
H
l
I
H
I
H-C-H
I
H
"
c
(C)
c
H
H
The IUPAC name for the structure is
(D)
I
H
Cl
Cl
H
(A)
(B)
. (C)
'\
I
H-C-H
2.
I
H
H-C-C -C-C-H
H H
I
C- H
r
H
H
I
Item 2 refers to the following structure.
H H H.
I
!
(B)
H
----,
2- ethyl butane
3 - ethyl butane
2 - methyl pentane
3 - methyl pentane
c
"/ c
/
II'- H
I
H
Br
H
H
"
c
(D)
c
"
/
c
H
/j"H
H
I
H
GO ON TO THE NEXT PA ~,
I
I
-34.
I:,
I:::~
l
l
L
5.
Volatility of organic compound s depends
on the strength of the inten11olecular forces
present. Which compound below would be
the MOST volatile?
(A)
(B)
(C)
CH3 CH2 CH2 0H
CH 3CH2CH2CH3
CH 3CH(CH3 )CH 3
(D)
CH3CH2CH2COOH
I.
II.
III.
l_
(A)
(B)
(C)
(D)
Which of the following alcohols will N The
oxidised by acidified potassium die mate
(VI)?
(A)
~H1 0H
CH1 0H
(B)
In the reaction between ethene and
bron1ine, which statemen ts about the
reaction mechanism are true?
I_
L
6.
I
I
CH- C - H
3
OH
A carbocatio n forn1s in the rate
detennini ng step.
A dative covalent bond forms
between the bron1ide ion and the
carbocatio n.
Heterolyti c fission of the brominebromine bond occurs.
H
I
(C)
CH -CH - C - O H
1
3
I
CH 3
CH 3
I and II only
I and III only
II and III only
I, II and III
(D)
I
I
CH- C - OH
3
CH 3
l_
7.
The equation for the fom1ation of the a aesthetic, CF3CHBrCl, is
l_
Br2
L
l_
> CF3CHBrCl
The type of reaction occun·ing is
(A)
(B)
(C)
(D)
electrophilic substitution
free radical substitution
nuc.Ieophilic addition
nucleophilic substitution
GO ON TO THE NEXT P
r
-48.
Ethanol can be fonned by the fo11owing
reaction
10.
oes
Which of the following compoun
NOT give a white precipitate when h ken
with cold ethanolic silver nitrate?
(A)
The mechanism used is
(A)
(B)
(C)
(D)
eJectrophilic addition
nucleophilic addition
electrophilic substitution
nucleophilic substitution
Cl
(B)
I
i
i
Iten1 9 refers to folJowing diagram of
Compound A.
I
I
CJ
(C)
0
I
I
I
II
i
(D)
I
I
nc==cn2
Compound A
9.
Which statements are cmTect concerning
Cmnpound A?
I.
II.
111.
(A)
(B)
(C)
(D)
I
11.
It will decolourize aqueous
bromine.
It will decolourize cold, acidified
potassimn pennanganate.
It will produce a silv~r mirror with
Toll en's reagent.
I and Il only
I and 11 I only
II and JII only
I., II and HI
Which of the foJJowing would rei
proton MOST readily?
(A)
(B)
(C)
(D)
12.
CH 3CH 20H
CH.COOH
·'
C"'H 50H
CH 30H
Hydrogen cyanide is more likely to
ethanal but not to ethene because
(A)
(B)
(0)
f
a
I
!
i to
I
i
ethanal is more susceptible Ito
e)ectrophilic attack than et ~:~i,1e
ethan~ I is more susceptible t tl' jee
rsd1caf
(C)
l
attack than ethene
1
ethanal is more susceptib ito
nucleophilic attack than et et~e
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
tyrosine.
16.
I
Which of the following may be elimi ~fed
by calibrating a measuring instrume t I
(A)
(B)
(C)
(D)
1\~
1
I
i
I
'.:i
17 .
l !'
... ..~
·;;:J:
j·[
Lack of precision
Random en-ors
Systematic errors
Random and systematic erro s
Which of the following is NOT apr
of a prhnary standard?
Does not undergo hydrolysi
Has low relative molecular
Is obtainable in a pure state.
Is very soluble in water.
(A)
13.
The pH of tyrosine is MOST likely
(A)
(B)
(C)
(D)
14.
2.1
5.6
7.0
9.0
(D)
18.
Which of the following is NOT true of
addition poly1nerisation?
(A)
(B)
(C)
(D)
15.
(B)
(C)
Only one type of polyn1er is
fon11ed.
The 1nolecular mass of the polymer
is a multiple of the monomer
unit.
The polymer is readily hydrolysed
to the monomer.
The physical and chetnical
properties of the polymer are
different fron1 those of the
n1onon1er.
The product fanned by the polymerisation of
propene, C 3H 6 , may be used as a
(A)
(B)
{C)
(D)
fuel
liquid
disinfectant
plastic material
I
1
's.
Which of the following will NOT
the accuracy of the results in a titri
analysis?
(A)
(B)
(C)
(D)
19.
;rty
i
Adding excess water to the c
flask
Blowing the reagent out
pipette tip
Overshooting the calibration
of the volun1etric flask
Purity of reagents
A 300 mg solid sample containing ch
is dissolved in water. The chloride i
precipitated as AgCl by the additi
silver nitrate to the solution of the sa
The precipitate is collected, washed,
and weighed, and found to have a m
525 mg.
(R.A.M. ofCl = 35.5, Ag = 108)
The mass of chloride present in the sat
(A)
(B)
(C)
(D)
74.2 mg
118.0 mg
129.9 mg
208.0 mg
i
GO ON TO THF. NEXT PA
fli
-620.
Which of the following statements about
gravimetric analysis is NOT true?
(A)
(B)
(C)
(D)
21.
(A)
(C)
(D)
22.
(C)
(D)
25.
III.
(A)
(B)
(C)
(D)
(C)
(D)
Shot1 wavelength and low energy
fi~equency
Which ofthe following types of electronic
transitions would NOT produce absorption
in the UVNIS region ofthe spectrum?
26.
;s a
large difference in energy b
the bonding and antib
orbitals
large difference in energy b
the bonding and non-b
orbitals
small difference in energy b
the bonding and non-b
orbitals
sma11 difference in energy b
the bonding and antibo
orbitals
Which of the following pairs will NOT
infrared radiation?
I.
II.
Mass spectroscopy
UVNIS spectroscopy
Gas chromatography
Thin-layer chromatography
Long wavelength and high energy
Long wavelength and low
frequency
Short wavelength and high
(B)
23.
(B)
Which two features BEST describe ultraviolet radiation?
(A)
Hexane will not absorb light in the U
region of the spectrum because ther
(A)
Gravimetric analysis is a purely
quantitative method.
Gravimetric analysis never
involves the removal of volatile
components of a solid~
The analyte can be identified after
precipitation and isolation have
occurred.
The amount of analyte lost due
to solvation is assumed to be
negligible.
Which of the following analytical techniques is considered MOST specific for
identification purposes?
(B)
24.
H:! and Cl 2
NH 3 and HBr
CH4 and Br1
I only
11 only
I and III only
II and III only
Which of the following statements ab
patiition coefficient may be true?
l.
I1.
HI.
(A)
(B)
(C)
s __... p*
(A)
p-+ p"'
n __... p*
(B)
{C)
(D)
n-+ s*
(D)
It does not vary with temperat r ;.
The so Jute has to be in the ,1pe
molecular state in both sol e.nts
for it to be a constant.
be
The two solutions have
con centra ted for it to <i' a
constant.
I only
11 only
J and l1 only
I. II and Ill
GO ON TO THE NEXT PA
-...,
-7-
27.
Which of the follow ing is NOT a station ary
phase used in chron1 atograp hy?
(A)
(B)
(C)
(D)
l
30.
Alumi na
Cellulo se
Silica gel
Starch
Which of the followi ng are advant g is of
I
stean1 distilla tion?
I.
II.
Ill.
i
(B)
(C)
I and II only
I andl Ill only
II and III only
(D)
I, 11 and III
(A)
··
Item 28 refers to the followi ng inform ation.
..I
.
A studen t canies out an experim ent using
thin-la yer chron1 atograp hy separat ion on
silica gel and obtains the followi ng results:
j
Compo und
Compo und A
Compo undB
Solven t
28.
(D)
29.
I
I
31.
Distan ce Travel led
(em)
(A)
(B)
(C)
(D)
0.07
0.16
0.73
0.054
0.54
5.4
54.0
?f a
i
IV.
(A)
(B)
(C)
(D)
I, II and III only
I, II and IV only
I, Ill and IV only
I, II, III and IV
III.
0.12
pa1tition coefficient is
l~ors
1
Prox~mity.t~ a potential work o~:ce
Avail ability to a mea s iI of
.
,
transpm 1atwn
Potenti al polluti on of air, lat · nd
water
Proxim ity to raw materials
I.
II.
1.5
9.1
12.5
A solutio n of 10 g of a carbox ylic acid
(weak acid) in 100 cm 3 of water is shaken
3
with 100 cm of ethoxy ethane . It is found
that only 6.5 g of the acid remain s in
aqueou s solutio n at equilib rimn. The
Which of the following are important
to conside r in detenni ning the locati
factory?
I
The Rr value of Compo und A is
(A)
(B)
(C)
I
It occurs under reduce d pre s~re.
The compon ents do not deco 1~ose.
t.
It provid es savings in fuel
32.
Along with silicon dioxide , which
following compou nds constitutes the
impurities of bauxite?
(A)
(B)
(C)
(D)
lron(II) oxide
lron(IIJ) oxide
Carbon dioxide
Carbon monoxide
GO ON TO THF. NF.XT PAr,
-8Item 33 refers to the follo wing fractions of
crud e oil.
I.
II.
III.
IV.
33.
Dies el
Petrol
Refin ery gas
Kero sene
(A)
In the elec troly sis of brin e u ing the·
diap hrag m cell, two by-p rodu c s re
(A)
(B)
chlo rine and oxyg en
(C)
hydr ogen and merc ury
hydr ogen and sodi um h
(D)
The corre ct orde r in tenn s of INCR EAS ING
boiJing poin ts is
(B)
(C)
(D)
37.
38.
I, II, Ill, IV
III,I ,IV, II
III, II, IV. I
IV, II, I, Ill
The prese nce of phos phat e ions ( . 4J-) can
be detec ted usin g
(A)
(B)
(C)
(D)
34.
Whi ch of the follo wing prod ucts is NOT
prod uced for comm ercia l purp oses by the
e]ectroJysis of conc entra ted brine ?
(A)
(B)
(C)
(D)
35.
(B)
(C)
(D)
36.
(A)
(C)
y
Amm oniu m salts
Amm oniu m salts
Naph tha
Air
Air
n.
Naph tha
Amm oniu m salts
IIJ.
IV.
Dete rgent
(A)
(B)
(C)
(D)
I. II and Ill only
1, Ill and lV only
II, Ill and JV only
L 11, JH and JV
(C)
(D)
I.
tion
I
1
.
II p I11tes
s~
Whi ch of the follo wing
sulph uric acid'?
Air
consumption?
l
l
1
J
.ecause
1
I
I
impr ove the flavo ur of ft i
help to enha nce the colo ~f food
inhib it the oxid ation ofun a: trated
fats
by
help to pres erve the
dehy drati on
Fet1ilizer
Paint
Fibre
Whi ch of the follo wing state men ts does
ol
NOT accu rateJ y desc ribe a resul t of ethan
(A)
(B)
(D)
40.
ate( II)
C mnp oun ds o f· su lP.I1~r sue I1 .as.
(B)
X
amm oniu m moly bdat e
pota ssiu m hexa cyan o
solut ion
pota ssium thioc yana te s
sodiun1 thios ulph ate
are used as food addit ives. This
they
Chlo rine
Oxyg en
Hydr ogen
Sodi um chlor ate (V)
In the Bosc h-Ha ber proc ess, N., and H~ can
be obta ined from X and Y respecti~eJy.
T
Whi ch of the follo wing pair s BES
Y?
desc ribes X and
(A)
39.
chlorine and sodium
use
-
Dige stion occu rs in the stom ach.
Natu ral inhi bitio ns are re]ax ed
(redu ced) .
Oxid ation occu rs in the bloo d.
Reac tion time is redu ced.
GO ON TO THE NEX T P
Cftf.
I
.
-9-
.
41 .
'.·
(A)
(B)
(C)
(D)
_~i
Deni trifying
bacteria
J:l,
1
J1t
·:t.f•. t;;:.:·1
··;o-.:,-•·
'l'i~t···
-·I
_j ·.
_j
A bala nced equa tion for the pho toch emi
deco n1po sitio n of Freo n- II is
CC13F(g)
hr ) 2Cl• (g) + CCI F•
(B)
CC13F(g)
hr > CCl •(g) + F•(g )
3
(C)
CC13 F(g)
hf ) Cl•( g) + CCl F•(g )
2
CC13F(g)
hr ) 3Cl• (g) + CF• (g)
(D)
43.
wr. .._D eca y.
Organic
N
2
4
Plants
J
l
y
J
I
i.i
compounds
Bacteria
Bacteria ...
I
I
~
44.
W would MO ST JikeJy be
(A)
(B)
(C)
cal
(A}
Nitrifying
) bacteria
,
f~~~r
n-11 ,
Aer oso l prop ella nts such as Freo
use of
CC13 F, are of 111ajor con cern beca
e,
thei r photochen1icaJ reac tion with ozon
ere
0 3 • Ultr avio let radi atio n in the strat osph
th(m
ch
whi
,
cals
radi
rine
prod uce s chlo
reac t with ozon e, prod ucin g oxy gen.
42.
atic
Li
!X
J
desc ripti on:
.ii,i·
1
-,
Nitrogen _., N2 ~~--:-:R:-:-ai_n7a_n_d-tt--;r
g
tnin
ligh
fixation ...-l
Amn 1oni a
Car bon diox ide
Met han e
Wat er vap our
Item s 42- 43 refe r to the foll owi ng
j ~ :~~-
Item 44 refe rs to the follo wing sch
diag ram .
nWhi ch of the follo win g is NO T a gree
hou se gas?
(D)
45.
nitrates
nitrites
nitri c(V) acid
amm oniu m salts
Wh ich of the foll owi ng plas tic
biod egra dabl e?
(A)
(B)
(C)
(D)
Low dens ity poly ethe ne
Poly then e tere phth alate .
Po1y (3 - hydr oxyb utan o1c ac
Poly viny lchl orid e
~~ re
:
.
1
dO
I
i
on of
A bala nced equa tion for the prod ucti
is
ne
ozo
from
oxy gen
(A)
(B)
(C)
(D)
0 1(g) + Cl·(g)---.. O(g ) + CIO , •(g)
O~(g) + Cl•(g)---.. CIO •(g) + 0 7 (g)
O~(g) + CI-( g) ~ O(g ) + ClO.,:(g)
O~(g) + CI-(g)---.. O.,(g) + CJO -(g)
END OF TES T
TE ~ ~.
CH EC K YO Uil WO RK ON TH IS
n1
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ntr " nu
" l n l "l