C

CHEMI
ISTRY OLYM
MPIAD PRAC
CTICE T
TEST-1
TIME : 2 HR.

D
DATE
: 16-11-2012

MARK
KS : 160

1. A C6H12 compou
und reacts with
w ozone to
t yield a siingle C3H6O product. G
Gas phase free
f
radical bromination
n of the hyd
drocarbon gives a single C6H11Br product.
p
A likely identiffication
of this compound
c
is.
(A) cycllohexane
(C) 3-he
exene

(B) cyclohexene
(D) 2,3--dimethyl-2-butene

2. The terpene
t
ocimene has the
t IUPAC name
n
(3E)-3,7-dimethyyl-1,3,6-octa
atriene, wha
at is the
structurral formula of
o this comp
pound?

ethylcyclobu
utanes is ch
hiral ?
3. Whicch of the folllowing dime
(A) tran
ns-1,2-dimetthylcyclobutane
(C) tran
ns-1,3-dimethylcyclobutane

(B) cis-1,2-dimethyylcyclobutan
ne
(D) cis--1,3-dimethyylcyclobutane

4. Whicch of the folllowing C6H12

h the larg
gest heat of combustion
n?
1 isomers has
(A) cycllohexane
(C) ethyylcyclobutan
ne

(B) metthylcyclopen
ntane
(D) propylcyclopro
opane

5. The radical
r
halo
ogenation off 2-methylpropane give
es two products: (CH3)2CHCH2X (minor)
and (CH
H3)3CX (majjor) Chlorin
nation givess a larger am
mount of the
e minor pro
oduct than does
d
bromina
ation, Why?
?
(A) Bromine is morre reactive than
t
chlorin
ne and able to attack th
he less reacctive 3C-H.
(B) Bromine atomss are less re
eactive (more selective
e) than chlorine, and prreferentially
y attack
the wea
aker 3 C-H bond.
(C) The
e methyl gro
oups are mo
ore hindered
d to attack by the large
er bromine a
atom.
(D) Bromination is reversible and
a the more stable 3-alkyl brom
mide is forme
ed exclusively.
6. Whicch of the folllowing is no
ot an electro
ophile?
(A) C2H5OC2H5
(C) [CH
H3]3C(+)

(B) BF3
(D) HOCl

7. Whicch of the folllowing strucctures would

d be consid
dered an en
nol tautomerr of
cyclope
entanone?

8 Two C5H8 isomers undergo catalytic (P

Pt) hydrogen
nation to forrm the same
e C5H10 pro
oduct.
On ozonolysis follo
owed by oxiidative workkup (H2O2), one isomer gave a C5H8O4 diacid
d, while
the othe
er isomer ga
ave a C5H8O3 ketoacid
d.Which of the
t following
g isomeric p
pairs corres
spond to
this evid
dence?
(A) cycllopentene and
a 1-pentyyne
(B) cycllopentene and
a 1-methyylcyclobuten
ne
(C) 1-m
methylcyclob
butene and 3-methylcyclobutene
(D) cyclopentene and
a 3-methyylcyclobutene
9. Whicch of the folllowing compounds hass two or mo
ore conjugatted double b
bonds?

10. A C8H12 chiral hydrocarbo

on, X, is reduced by cattalytic hydro
ogenation to
o an achirall C8H14
compou
und. Ozono
olysis of X (H
H2O2 workup) gave a chiral
c
C8H12O4 dicarboxxylic acid. Which
W
of
the follo
owing could
d be X ?

11. Cycclooctatetrae
ene, C8H8, appears to be a conjug
gated annulene. In ad
ddition to the
planar configuratio
c
on, three non-planar strructures ma
ay be consid
dered, all off which are shown
below. Which of th
hese is mosst likely to be
b the favore
ed conformation? notte that D is planar.

12. Which of the fo

ollowing is the correct configuratio
c
onal prefix fo
or the follow
wing diene?

(A) (2E,4E)

(B) (2Z,4Z)

(C) (2Z,4E)

(D) (2E
E,4Z)

13. Which of the fo

ollowing con
nformationa
al structures
s is 2-methyylpentane ?

14. Wh
hich isomer of hexane has only tw
wo different sets
s
of struccturally equ
uivalent hydrogen
atoms.?
?
(A) 2,2--dimethylbutane
(C) 3-m
methylpentan
ne

(B) 2-m
methylpentan
ne
(D) 2,3--dimethylbu
utane

15. The
e monochlo
oroisomer th
hat predomiinates in the
e mixture re
esulting from
m the free ra
adical
chlorina
ation of CH3CH2CH2CH
H=CH2 is
(B).CH3CHClCH2CH=CH
C
2
(D)..CH
H3CH2CH2CCl=CH2

(A).ClC
CH2CH2CH2CH=CH
C
2
(C).CH3CH2CHClC
CH=CH2

16. Wh
hich is NOT
T characterisstic of a free
e radical chain reaction
n?
(A).It prroduces a mole
m
of prod
duct for a mole
m
of free radical
r
initia
ated.
(B) It gives
g
the pro
oduct derive
ed from the most stable free radiccal.
(C) It may
m be initia
ated by pero
oxides.
(D) It may
m be initia
ated by high
h heat.
17. Wh
hich anion iss the weake
est base?
(A). C2H5O1(C) CN1-

(B).NO31(D).CH3COO1-

18. Wh
hich of the amines
a
liste
ed below wo
ould have th
he lowest bo
oiling point?
?
(A). CH
H3CH2CH2NH2
(C). (CH
H3)3N

(B).CH3CH2NHCH3
(D).(CH
H3)3CNH2

19. Exa
amine the reaction
r
sho
own below and
a then predict what product
p
wou
uld be formed.
H3C CH2 CH2 Mg
M Br

H3C C CH2 CH2 CH3

O

(A)

(B)

(C)

(D)

20.Which one of the following does not correctly describe one or all of the hydrogen halides,
HX?
(A) Their aqueous solutions are acidic.
(B) HF has the lowest of the H-X bond energies.
(C) HI is the largest.
(D) HCl has the lowest boiling point.
21.Of the oxyacids listed below, which one possesses the greatest acid strength in water?
(A) HClO4
(C) H3BO3

(B) H2CO3
(D) HClO

22.Which statement about the Group VIA hydrides is false?

(A) H2S, H2Se and H2Te are gases at room temperature and atmospheric pressure.
(B) All are colorless.
(C) All except H2O are toxic.
(D) H2Po has the lowest boiling point.
23.What maximum mass of sulfuric acid can be produced from the sulfur contained in 100
kilograms of iron pyrite that is 75.0% FeS2?
(A) 84.4 kg
(C) 136 kg

(B) 123 kg
(D) 144 kg

24.In which one of the following is the oxidation state of nitrogen given incorrectly?
(A) N2O3, +3
(C) HNO3, +5

(B) N2H4, +2
(D) NaNO2, +3

25.Which of the following does not correctly describe ammonia?

(A) pyramidal molecule
(C) extremely soluble in water

(B) polar molecule

(D) none of these

26.Which compound gives photochemical smog a brownish color?

(A) NO
(C) NO2

(B) HNO2
(D) N2O4

27.What is the major mineral present in phosphate rock?

(A) Ca3(PO4)2
(C) Ca10(PO4)6F2

(B) Na2HPO4
(D) NaH2PO4

28.Which one of the following salts is insoluble?

(A) NH4Cl
(C) BaCO3

(B) Ca(NO3)2
(D) Zn(CH3COO)2

29.Which of the following statements is FALSE given the following net ionic equation?

H3PO4(aq) + 3OH-(aq)

PO43-(aq) + 3H2O(l)

(A) If all the water evaporated away, the salt remaining could possibly be Na3PO4.
(B) The acid, H3PO4, is a weak electrolyte.
(C) The base involved must be a strong soluble base.
(D)This could be the net ionic equation for H3PO4 reacting with Al(OH)3.
30.Given that the Activity Series is: Na>Mg>Cu>Ag>Au, which one of the following answers
represents the ions that would not be displaced from aqueous solution (reduced) by metallic
magnesium?
(A) Na+
(C) Cu2+ and Au+

(B) Cu2+
(D) Cu2+, Ag+ and Au+

31.Which name/formula combination is WRONG?

(A) chlorous acid / HClO2
(C) ammonium nitrate / NH4NO3

(B) dinitrogen tetroxide / N2O4

(D) copper(II) periodate / CuIO4

32.In the gold plating process, sodium cyanide solution is used as an electrolyte instead of
nitric acid because
(A).cyanide forms a complex with gold and thus helps uniform deposition of gold
(B).sodium cyanide is a better solvent for gold ions
(C).cyanide binds with impurity ions and keeps the impurities in solution
(D).deposition of gold from nitric acid bath is slow
33.Sodium hydroxide cannot be used as a primary standard for acid base titration because
(A).it is corrosive and reacts with glass
(B)the dissolution of sodium hydroxide in water is highly exothermic, hence its
concentration changes on dissolution
(C)it is hygroscopic and also reacts with atmospheric carbon dioxide
(D)hydroxides cannot be used as primary standards
34.The diagonal relationship of elements in the periodic table arises because of similarity in
(A).ionic radius
(C)crystal structure

(B)electronic configuration
(D)charge/radius ratio of the corresponding ions

35.The metal that can be extracted from its oxide by reduction with carbon is
(A)sodium

(B)calcium

(C)iron

(D)aluminium

36.Chromium has the lowest oxidation state in

(A).chromium sulphate
(C)potassium chromate

(B)chromium trioxide
(D)potassium dichromate

37.The anhydride of nitric acid is

(A).nitric oxide
(C)dinitrogen trioxide

(B)nitrous oxide
(D)dinitrogen pentoxide

38.The molar conductivities of H+, Li+ and Na+ ions in aqueous solutions at infinite dilution

are in the order

(A).H+ > Li+ > Na+
(C)H+ > Na+ > Li+

(B)H+ < Li+ < Na+

(D)Na+ > H+ > Li+

39.Sodium chloride crystallizes in a face centered cubic lattice in which each

(A).sodium ion is tetrahedrally surrounded by 4 chloride ions and each chloride ion is
tetrahedrally surrounded by 4 sodium ions
(B)sodium ion is tetrahedrally surrounded by 4 chloride ions and each chloride ion is
octahedrally surrounded by 6 sodium ions
(C)sodium ion is octahedrally surrounded by 6 chloride ions and each chloride ion is
surrounded by 4 sodium ions
(D)sodium ion is octahedrally surrounded by 6 chloride ions and each chloride ion is
octahedrally surrounded by 6 sodium ions
40.Generation of a blue colour which is not due to metal-ammonia complex formation is
seen when
(A)..sodium is dissolved in liquid ammonia
(B)copper (II) sulphate is reacted with ammonium hydroxide
(C)cobalt (II) chloride is reacted with ammonium hydroxide
(D)formaldehyde is reacted with ammonium hydroxide
41.Calcium gluconate syrup and calcium phosphate tablets are calcium supplements used to
treat calcium deficiency. However, calcium gluconate is preferred over the latter because it is
(A).more easily absorbed into the blood
(C)less toxic

(B)released slowly in the body

(D)more tasty

42.Milk of magnesia used as a medicine for treating indigestion is a substance that

(A).helps in disintegration of food products leading to their facile metabolism
(B)combines with gastric hydrochloric acid thereby enhancing the latters efficiency
(C)improves the enzymatic activities inside the stomach
(D)neutralizes excess acidity, providing a buffered medium inside the stomach
43.Carbon dioxide is gaseous, while SiO2 is solid because
(A).CO2 is a linear molecule, while SiO2 is an angular one
(B)the van der waals forces are very strong in SiO2
(C)CO2 is covalent, while SiO2 is ionic
(D)unlike C, Si cannot form stable bonds with O, hence S has to form a 3D lattice
44.K2S2O8, acidic K2S2O8 and acidic MnO2 oxidise I, Br, Cl to I2, Br2 and Cl2, respectively.
From the given data, the sequence that represents the correct order of increasing oxidising
ability is
(A).I2 > K2S2O8 > Br2
(C)K2S2O8 > I2 > Br2

(B)acidic MnO2 > K2S2O8 > Cl2

(D)Cl2 > K2S2O8 > Br2

45.The reaction 3O2(g) 2O3 (g) is endothermic. What can be concluded about the average
energy per bond in O2 and O3?
(A).the average energy per bond in O2 is greater than that in O3

(B)the average energy per bond in O2 is less than that in O3

(C)the average energy per bond in O2 is equal to that in O3
(D)no conclusions can be drawn about the average bond energies from this information
alone
46.When H2S is passed through a solution containing Cu2+, Cd2+ and an excess of cyanide
ions, cadmium sulphide precipitates while copper ions remain in solution. This is because
(A)Cu2+ forms a stable complex with cyanide while Cd2+ does not
(B)Cu2+ forms a more stable complex with cyanide than Cd2+
(C)Cu2+ does not form a sulphide
(D)both CdS and CuS are formed, but CuS is soluble
47.The acidic hydroxide is
(A).Ca(OH)2

(B)Al(OH)3

(C)B(OH)3

(D)TlOH

48.The blue pigment prussian blue is an iron complex with formula

(A).K4[Fe(CN)6]
(C)Fe4[Fe(CN)6]3

(B)K2[Fe(CN)4(NH3)2]
(D)Na2[Fe(CN)5NO]

49.A coordination complex of type MX2Y2 [M = metal ion; X,Y = monodentate ligands], can
have either a tetrahedral or a square planar geometry. The maximum number of possible
isomers in these two cases are respectively
(A)1 and 2

(B)2 and 1

(C)1 and 3

(D)3 and 2

50.Platinum metal (Pt) dissolves in aqua-regia but not in concentrated HCl or HNO3 because
(A).HCl oxidizes Pt in the presence of HNO3
(B)HNO3 reacts with HCl to form chlorine which attacks Pt
(C)HNO3 oxidizes Pt which is followed by formation of a chloro complex
(D)HCl and HNO3 together give O2 that oxidizes Pt
51.The least stable metal carbonyl as per the bonding considerations should be
(A)Cr(CO)6

(B)Mn(CO)6

(C)Fe(CO)5

(D)Ni(CO)4

52.Dimethyl glyoxime forms a square planar complex with Ni2+. This complex should be
(A)diamagnetic
(B)paramagnetic having 1 unpaired electron
(C)paramagnetic having 2 unpaired electrons
(D)ferromagnetic
53.The compound that cannot be formed by xenon is
(A).XeO3
(C)XeCl4

(B)XeF4
(D) XeOF4

54.SnCl2 acts as a reducing agent because

(A).SnCl2 can accept electrons readily
(C)Sn4+ is more stable than Sn2+

(B)Sn3+ is more stable than Sn2+

(D)Sn2+ can be readily converted to metallic tin

55

56. What compound will be formed from the peroxide-catalyzed addition of HBr to 1hexyne?
(A)CH3CH2CH2CH2CBr=CH2
(C)CH2BrCH2CH2CH2CH=CH2

(B)CH3CH2CH2CH2CH=CHBr
(D)CH3CH2CH2CBr=CHCH

57.What product is formed when 1-butyne undergoes hydroboration-oxidation?

(A)CH3CH2-CH=CH(OH)
(C)CH3CH2-C(=O)-CH3

(B) CH3CH2-C(OH)=CH2
(D)CH3CH2CH2CH=O

58.Calculate U for a system that loses 325 kJ of heat while doing 200 kJ of work on the
surroundings.
(A)+125 kJ

(B)

-525 kJ

(C)

0 kJ

(D)

-125 kJ

59.When 1 mole of white tin changes to gray tin at 13.0oC, the change in entropy is -7.5 J
K-1. This means that
(A)the change from white to gray tin is predicted to be spontaneous on the basis of the
entropy change.
(B)gray tin has an entropy of -7.5 J K-1.
(C)gray tin is more ordered than white tin.
(D)gray tin has a higher molar entropy than white tin.
60.Which one of the following statements is true?
(A)Spontaneous reactions always have Hro < 0.
(B)Reactions with positive values of Sro always become spontaneous at high
temperatures.
(C)All of these statements are false.
(D)Spontaneous reactions always have Hro > 0.
61.Which of the following statements about colligative properties is TRUE?
(A)Both vapor pressure and freezing point INCREASE when a non- volatile solute is added
to a solvent.

(B)Both freezing point and boiling point INCREASE when a non- volatile solute is added to a
solvent.
(C)Both vapor pressure and boiling point DECREASE when a non- volatile solute is added to
a solvent.
(D)Colligative properties depend only upon the NUMBER of solute particles in a solution and
not upon their identity.
62. Calculate the PERCENT BY MASS of hydrogen peroxide (H2O2, MW = 34.0 g/mole) in a
5.88 M solution of H2O2 in water. The density of the solution is 1.00 g/mL.
(A) 1.00%

(B) 3.00%

(C) 5.00%

(D)20%

63. In visible spectroscopy, the wavelength at maximum absorbance (lambdamax) is usually

used for a spectrophotometric analysis because
(A) chemical substances only absorb visible light at a single wavelength, lambdamax
(B) the change in absorbance per unit change in concentration is largest at this wavelength
(C) the change in absorbance per unit change in concentration is smallest at this
wavelength.
(D) chemical substances absorb visible light equally well at all wavelengths.
64. In order for a solution to form spontaneously at a given temperature, the change in free
energy for the formation of the solution ( Gsoln) must be negative. Which of the following
thermodynamic properties is primarily responsible for determining whether or not a solution
will form?
(A)

Ssoln

(B)

Hsoln

(C)

Wsoln

(D)

Esoln

65.Which of the following contains TWO anions that form soluble salts with most metal ions
and TWO anions that form insoluble salts with most metal ions?
(A)Sulfate, hydroxide, chromate, sulfide

(B)Nitrate, hydroxide, chromate, sulfide

(C)Chloride, hydroxide, chromate, sulfide

(D)Nitrate, chloride, hydroxide, sulfide

66.Consider an aqueous solution that contains 0.10 M each of Pb2+, Hg2+ and Ni2+. If a
solution containing 2.0 x 10-20 M S2- is added to the solution containing the metal ions, which
sulfides will precipitate from the solution?
PbS: Ksp = 8.0 x 10-28; HgS: Ksp = 4 x 10-53; NiS: Ksp = 3.2 x 10-19
(A)PbS, HgS and NiS

(B)PbS and HgS

(C)HgS
S and NiS

(D)NiS only

67.Fluo
orine-18 is one
o of the ra
adioactive nuclides
n
utilized in Positron Emisssion Tomogrraphy
(PET) scans.
s
Fluorrine-18 can be synthessized by bom
mbarding oxygen-18 n
nuclei with
hydroge
en-1 nuclei,,
oxygen-18 + hydro
ogen-1 --> fluorine-18 + X
What iss the identityy of the othe
er product, X, in this re
eaction?
(A)alpha particle

(B)beta
a particle

(C)positron

(D)neuttron

68. Which of the fo

ollowing com
mpounds fo
orms ortho-b
benzenedica
arboxylic accid when ox
xidized
by hot aqueous
a
po
otassium pe
ermanganate
e?

69.

Following represents
r
e
equation
of state for n moles of real gas

n 2a
P
+
[ V nb ] = nRT

V2

Se
elect correcct statementts :

n 2a
2
(A)
Constant a is a measu
ure of force of attraction
n between gas
g molecu
ules and V is
also called internal pressure
(B)

ed in L mol1
a is expressed in atm L2 mol2, b is expresse

(C)

At high pressure, compression factor is

(D)

All of the ab
bove are co
orrect statem
ments

Pb

1 +

RT

on involving a single re
eactant in each case, a plot of ratte of the
70.The three differrent reactio
reaction on
n the y-axis,, versus con
ncentration of the reactant on the x-axis, yield
ds three
different cu
urves shown
n below :

10

(i) dc

(iii) dc

(ii) dc

dt

dt

dt

what are the possible orders of the reactions (i), (ii), (iii).
(A) 1, 2, 3

(B) 2, 1,

1
2

(C) 0, 1, 2

(D) 0, 1,

1
2

71

A mixture of N2O4(g) and NO2(g) under equilibrium has an average molar mass of 76.
The mol-fraction of N2O4 at equilibrium and the percent N2O4 dissociated are

(A)

0.6 and 25

(B)0.8 and 40

(C) 0.6 and 33.3 (D) 0.7 and 50

72. Which of the following amines could be made successfully in a Gabriel synthesis?
(A) aniline

(B) benzyl amine

(C) dimethyl amine

(D) trimethyl amine

73. Which compound would NOT be readily made from benzenediazonium chloride?
(A) chlorobenzene

(B) iodobenzene

(C) benzonitrile

(D) benzoic acid

74. Reductive amination of acetophenone with methyl amine would give

(A) N-methylaniline

(B) N-methyl-1-phenylethylamine

(C) N,N-dimethylaniline

(D) N-methylbenzylamine

75. The compound below that will be most reactive in a nucleophilic substitution reaction is
(A) p-chlorotoluene

(B) p-fluorotoluene

(C) p-chloronitrobenzene

(D) p-fluoronitrobenzene

76. The cyclic transition state in the Claisen rearrangement involves reorganization of how
many electron pairs?
(A) 1

(B) 2

(C) 3

(D) 4

77. A example of an aldohexose is

(A) glyceraldehydes
(C) ribose

(B) erythrose
(D) glucose

78. The anomeric carbon of fructose is

11

(A) C-1

(B) C-2

(C) C-3

(D) C-4

79. A pyranose ring is created by connecting the C-1 of glucose to the O on

(A) C-1

(B) C-2

(C) C-3

(D) C-5

80. The C-4 epimer of D-glucose is

(A) D-fructose

(B) D-ribose

(C) D-mannose

(D) D-galactose

12