Sri Lanka National Chemistry Olympiad

Preliminary Selection Test – 2023

Answer ALL questions Number of Pages 14 Time: 2 hours and 30 minutes

Composition: 45 Multiple Choice Questions
a. Should indicate all your answers in the answer boxes provided to you.
b. Select the best answer out of the five choices for each question and mark a cross using a carbon pen
(blue/black) as shown below.

(a) (b) (c) (d) (e)

17.

c. Mark only one answer to each question. (Marks will not be given for marking more than one answers.)
d. Clearly write your index number on the top right-hand corner of the answer sheet.

Calculators (scientific and normal) are allowed, but any other electronic devices (smart watches) are not
allowed.

Physical Constants

Gas Constant 8.314 J mol-1 K-1 Avogadro Number 0 °C = 273 K

6.022 × 1023 mol-1 1 atm = 760 mm Hg = 1.013 bar

Plank constant 6.6 × 10−34 m2 kg s-1 Standard temperature and pressure: 273 K and 100 kPa

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(1) Place the following ions in order of increasing size: Al3+, P3−, and S2−
(a) P3− < S2− < Al3+ (b) Al3+ < P3−< S2− (c) Al3+ < S2− < P3−
(d) P3− < Al3+ < S2− (e) S2− < Al3+ < P3−

(2) Homolysis of a C-C bond forms

(a) two Carbocations (b) two Carbanions (c) Carbocation and a Carbanion
(d) two radicals (e) radical and a carbocation

(3) A fuel/oxidant system consisting of N,N-dimethylhydrazine, (CH3)2NNH2, and dinitrogen

tetraoxide, N2O4, (both liquids) is commonly used in space vehicle propulsion. The
components react stoichiometrically to form only N2 (g), CO2 (g) and Η2Ο (g). How many
moles of gas are produced from 1 mol of (CH3)2NNH2 with excess N2O4?
(a) 8 (b) 9 (c) 10 (d) 11 (e) 12

(4) Which of the following statements is best explained by resonance?

(a) The electron pair geometry of XeOF4 is octahedral.
(b) The bonds of NF3 are less polar than the bonds in CF4.
(c) CH3Cl contains three single bonds between carbon and hydrogen.
(d) All the bonds in BH3 have the same bond order.
(e) The NO3- exhibits only one type of N-O bond.

(5) The hybridization of phosphorous in PCl3 is the same as in

(a) S in SF4 (b) C in C2H2 (c) P in POCl3 (d) Cl in ClF3 (e) B in BCl3

(6) A solution is prepared by mixing 4.0 mg of sodium ions (in the form of NaCl), 4.00 g of glucose
(C6H12O6), and 96 g of water. How many ppm of Na+ does this solution contain?
(a) 29.99 ppm (b) 33.44 ppm (c) 39.99 ppm (d) 78.98 ppm (e) 42.31 ppm

(7) How many structural isomeric alcohols can be drawn for the molecular formula C5H12O?
(a) 4 (b) 5 (c) 6 (d) 7 (e) 8

(8) The hybridization of how many atomic orbitals is involved in sp3 hybridization?
(a) 1 (b) 2 (c) 3 (d) 4 (e) 5

(9) To observe the adsorption capability of activated charcoal, 0.5 g of activated charcoal was
shaken with 50 mL of 1.0 mol dm-3 oxalic acid. The final oxalic acid concentration after
adsorption was found as 0.25 mol dm-3. Thus, how much oxalic acid has adsorbed per gram of
activated charcoal? (Oxalic acid molecular weight = 126 g/mol)
(a) 6.35 g (b) 4.72 g (c) 9.45 g (d) 5.25 g (e) 1.26 g

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(10) Which of the following represent the incorrect step/s of reaction mechanisms.

(11) What type of orbital is designated by the quantum numbers, n = 5, = 2, = +1?

(a) 5d (b) 2f (c) 5p (d) 2s (e) 5s

(12) Which of the following molecules is polar: H2S, CO2, NH3, BH3, and CCl4?
(a) BH3 (b) H2S and NH3 (c) H2S, CO2, and CCl4
(d) CO2, NH3, and CCl4 (e) NH3, BH3, and CCl4

(13) In the presence of NaOH methyl acetate hydrolyzes into acetic acid and methanol according
to the equation given below. Reaction occurs slowly at low temperatures.

CH3CH2COOCH3 (aq) + NaOH(aq) → CH3COONa (aq) + CH3CH2OH(aq)

150 mL of 0.06 M NaOH solution and 0.06 M methyl acetate solution were mixed in a conical
flask at 5 ℃. After 5 minutes 10.00 mL of the mixture was pipetted out and added to a titration
flask containing 10.00 mL of 0.05 M HCl. This mixture was titrated against 0.02 M NaOH
after adding a couple of drops of phenolphthalein indicator. End point volume of NaOH was
15.40 mL. Determine the OH- concentration of the reaction mixture in the conical flask at 5
minute. (Assume the reaction has not reached the equilibrium)
(a) 0.021 M (b) 0.0192 M (c) 0.210 M (d) 0.187 M (e) 0.40 M

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(14) Which of the following is not a suitable method to prepare benzaldehyde?
(a). Oxidation of toluene (b). Oxidation of benzyl alcohol
(c). Oxidation of methyl benzoate (d). Etard reaction (e). Reduction of benzoic acid

(15) Which pair from the below list shows an increasing order of the property given?
(a) Boiling point: I2 < Br2
(b) Electronegativity: F < O
(c) Third ionisation energy: Ar < Mg
(d) Radius: Na < Na+
(e) Covalent character: HI < HBr

(16) C2H6, CH3OH and CH3F have similar molar masses. Which of the following inequality
represents the correct trend in the boiling point of these molecules?
(a) CH3F = CH3OH = C2H6
(b) CH3OH < CH3F < C2H6
(c) CH3F < C2H6 < CH3OH
(d) C2H6 < CH3F < CH3OH
(e) C2H6 < CH3OH < CH3F

(17) Acetic acid concentration when 5.00 mL of glacial acetic acid is mixed with 170.0 mL of
distilled water is (the density, molecular weight and purity of glacial acetic acid are 1.05
g/mL, 60 g/mol and 97%, respectively.)
(a) 0.04 M (b) 0.17 M (c) 0.50 M (d) 0.019 M (e) 0.40 M

(18) Which of the following product/s is/are formed when the below compound (A) is reacted
with HBr followed by the reaction with alcoholic KOH?

(a) Only (1) and (2) correct (b) Only (2) and (3) correct
(c) Only (3) and (4) correct (d) Only (1) and (3) correct
(e) Any other number or combination of responses correct

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(19) Which of the given is the best reagent to accomplish the following conversion?

(a) Br2 in CCl4 (b) NaBr (c) Br2 in H2O (d) Conc HBr (e)

(20) Consider the process of cooling a glass of water under standard atmospheric pressure. At 0
℃, the water starts to solidify, forming ice. How do the following thermodynamic functions
change during the solidification of water at 0 ℃?

(a) 𝛥𝐻 = 0, 𝛥𝑆 = 0, 𝛥𝐺 =0
(b) 𝛥𝐻 > 0, 𝛥𝑆 > 0, 𝛥𝐺 =0
(c) 𝛥𝐻 < 0, 𝛥𝑆 < 0, 𝛥𝐺 >0
(d) 𝛥𝐻 < 0, 𝛥𝑆 > 0, 𝛥𝐺 <0
(e) 𝛥𝐻 < 0, 𝛥𝑆 < 0, 𝛥𝐺 =0

(21) Consider the process of heating water under atmospheric pressure higher than the standard
atmospheric pressure. By doing so, we can raise the boiling point of water. Suppose we have
liquid water at a temperature above 100 ℃ this way. Now the pressure dropped to the standard
atmospheric pressure. How do the following thermodynamic functions change immediately
after the standard atmospheric pressure is reached?

(a) 𝛥𝐻 > 0, 𝛥𝑆 > 0, 𝛥𝐺 <0

(b) 𝛥𝐻 > 0, 𝛥𝑆 > 0, 𝛥𝐺 =0
(c) 𝛥𝐻 < 0, 𝛥𝑆 < 0, 𝛥𝐺 >0
(d) 𝛥𝐻 < 0, 𝛥𝑆 > 0, 𝛥𝐺 <0
(e) 𝛥𝐻 < 0, 𝛥𝑆 < 0, 𝛥𝐺 =0

(22) Which one of the following species does not have eight valence electrons surrounding the
central atom?
(a) CCl4 (b) NH3 (c) NH4+ (d) OF2 (e) BCl3

(23) Which of the following alkyl halides would undergo SN1 reaction most rapidly?

(a) (b)

(c). (d) (e)

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(24) The second ionization energies for four consecutive elements of the Periodic Table W, X, Y
and Z, (they have atomic numbers n, n+1, n+2 and n+3) are 2297.3 kJ mol–1, 2665.8 kJ mol–
1
, 3051.3 kJ mol–1 and 1145.4 kJ mol–1, respectively. Which of the following pairs of oxides
would be the most stable?
(a) WO, X2O (b) X2O, YO2 (c) W2O, YO2 (d) XO3, Z2O (e) Y2O, ZO

(25) HgO + 4I- + H2O → HgI42- + 2OH-

In accordance with the above reaction 0.217 g sample of HgO (MW: 217 g) reacts with
excess iodide ions. After some time it was found that only 50% of HgO had reacted. If 0.05
M HCl was used to titrate the resulting solution, the volume of acid needed to reach the
end point would be,
(a) 1.0 mL (b) 10.0 mL (c) 20.0 mL (d) 50.0 mL (e) 100.0 mL

(26) What is the general method of preparation of benzene diazonium chloride below 5°C?
(a) Decarboxylation of benzoic acid
(b) Treating aniline with 20% NaNO2 in aqueous HCl
(c) Treating aniline with 20% NaNO3 in aqueous HCl
(d) Treating aniline with 20% NaNO2 in aqueous NaOH
(e) Treating aniline with 20% NaNO3 in aqueous NaOH

(27) Which of the following answers shows the reagents A-D in the correct order for the below
reaction scheme?

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(28) Which pair of diene and dienophile would lead to the product shown below?

(29) Elements W and X react to form an ionic compound. W and X have 2 and 6 valence electrons,
respectively. What is the formula of this compound formed from the reaction between W and
X?
(a) W2X6 (b) WX3 (c) WX (d) W3X (e) W6X2

(30) Consider the dissociation of a weak acid HA, defined by

𝐻𝐴 ⇌ 𝐻 + + 𝐴−
[𝐻 + ][𝐴− ]
𝐾𝐴 =
[𝐻𝐴]
The ionic product of water is given by KW = [H+][OH−]. Which of the following general
expressions is/are correct?
(X) [A−] = [H+]
(𝑌) [𝐴− ] = √𝐾𝐴 [𝐻𝐴]
1 [𝐻 + ]
(Z) [𝐴− ]
= [𝐻 +]2 −𝐾
𝑤

(a) Only X (b) Only Z (c) Only Y & Z (d) X, Y, & Z (e) Non of the expressions

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(31) The distribution coefficient of a compound A in a mixture of water and an organic solvent is
given by KD, i.e.,
[𝐴]𝑎𝑞
A(aq) ⇌ A(org); 𝐾𝐷 = [𝐴]𝑜𝑟𝑔
The compound A is dissolved in a volume V of water and is extracted 5 times using a
volume nV of the organic solvent. After the extraction, it was found that the aqueous layer
retained 1/32 of the original A content. Which of the following relationships is correct?
1 1
(𝑎) 𝑛 = 𝐾𝐷 (𝑏) 𝑛 = (𝑐) 𝑛 + 𝐾𝐷 = 1 (𝑑) 𝑛 = (𝑒) 𝑛 = 2/𝐾𝐷
𝐾𝐷 2𝐾𝐷

(32) Which of the following molecules XYn has the largest Y−X−Y bond angle?
(a) H2O (b) NH3 (c) CO2 (d) CF4 (e) BF3

(33)

In the reaction scheme above, the reagents and conditions of A to D, respectively are,
(a) Conc. H2SO4/heat, PBr3, dil. NaOH, K2Cr2O7/heat
(b) dil. H2SO4/heat, HBr, dil. NaOH, K2Cr2O7/heat
(c) Conc. H2SO4/heat, HBr, dil. H2SO4, K2Cr2O7/heat
(d) Conc. H2SO4/heat, HBr, dil. NaOH, K2Cr2O7/heat
(e) Conc. H2SO4/heat, HBr, dil. NaOH, K2CO3/heat

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(34)

What are the products obtained when the above compound is reacted with LiAlH4 followed by
neutralization of the reaction mixture?

Question 35 and 36 are related.

According to the Maxwell-Boltzmann distribution of the speed of gas molecules, the probability
of finding a molecule with speed 𝑣 is given by
𝑚 3/2 𝑚𝑣 2
𝑓(𝑣) = ( ) 4𝜋𝑣 2 e− 2𝑘𝑇 .
2𝜋𝑘𝑇

The root mean squared speed, 𝑣rms is given by

We can define two other characteristic velocities. The most probable speed 𝑣𝑝 is the speed most
likely to be possessed by a molecule. This is found by finding the derivative of 𝑓(𝑣) with respect
to 𝑣 and setting it to 0, i.e.,

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 𝑑𝑓(𝑣)
( ) = 0.
𝑑𝑣 𝑣=𝑣
𝑝

The mean speed is the average speed of the distribution, given by

These three characteristic speeds are related by

√𝜋 2
𝑣𝑝 = < 𝑣 > = (√ ) 𝑣𝑟𝑚𝑠
2 3

(35) The expressions for <v> and 𝑣𝑝 are

(36) As the temperature increases

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• Answer to the questions 39 to 40 based on the reaction given below.

(37) The correct structures of the products A and B respectively are,

(38) The absolute configuration of the C-1 and C-2 in the compounds A and B respectively are,

A B
C-1 C-2 C-1 C-2
(a) R R R S
(b) S R R S
(c) S S S R
(d) R R S S
(e) S R S S

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(39) For the stereochemical relationship between A and B, which of the following is/are true?
(1) Diastereomers
(2) Stereoisomers
(3) Identical
(4) Enantiomers

(a) Only (1) and (2) correct

(b) Only (2) and (3) correct
(c) Only (3) and (4) correct
(d) Only (1) and (3) correct
(e) Any other number or combination of responses correct
Question 40-41 are related
The electrons in conjugated linear polyenes can be studied using the particle in a one-dimensional
box model. Energy of the level n of a particle in a 1-Dimensional box model is given by

𝑛2 ℎ2
𝐸𝑛 =
8𝑚𝐿2
where h is Planck constant’s, m is mass of electron, and L is the box length.
(40) According to 1-Dimensional box model, which of the following would be the correct
expression for the absorption wavelength of a conjugated linear polyene of length L?
(𝑠𝑛)ℎ2 4𝑚𝑐𝐿2 8𝑚𝑐𝐿2 24 𝑚𝑐𝐿2 4𝑚𝐿2
a. (b) (c) (𝑑) (e) (2𝑛+1)ℎ
8𝑚𝐿2 2(𝑛+1)ℎ (2𝑛+1)ℎ (2𝑛+1)ℎ

(41) If L = (k+1)d where k is the number of C atoms in the conjugated linear polyene and the
average length of all C-C single and C=C double bonds is d, the correct expression for the
absorption wavelength of 1,3,5-hexatriene based on 1-Dimentional box model is
56𝑚𝑐𝑑2 16𝑚𝑐𝑑2 8𝑚𝑐𝑑2 32𝑚𝑐𝑑2
(𝑎) (b) (𝑐) (𝑑) (𝑒) 𝑛𝑜𝑛 𝑜𝑓 𝑡ℎ𝑒 𝑎𝑏𝑜𝑣𝑒
ℎ ℎ ℎ ℎ

(42) The electrons in anthracene can be considered as particles moving in a two-dimensional box
whose length is a and width is b. The energies of the π electrons in the box are defined by:

ℎ2 𝑛𝑥2 𝑛𝑦2
𝐸𝑛 = ( + ) 𝑤ℎ𝑒𝑟𝑒 (𝑛𝑥 = 1,2,3, . . ) & (𝑛𝑦 = 1,2,3, . . )
8𝑚 𝑎2 𝑏 2

Assuming a = 3b, find the HOMO level

(𝑎) 𝑛𝑥 = 1 𝑛𝑦 = 1 (𝑏) 𝑛𝑥 = 1 𝑛𝑦 = 2 (𝑐) 𝑛𝑥 = 2 𝑛𝑦 = 2 (𝑑) 𝑛𝑥 = 2 𝑛𝑦 = 3

(e) none of the above

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(43) Which of the following is the major organic product obtained from the following reaction?

(a) (b) (c)

(d) (e)

(44) Binding constants (Ka) of receptor L1 and L3 in a methanol: water mixture are given below
(T=293 K).

Anion

Anion L1 (X=I) (Ka (M-1)) L3 (X=Cl) (Ka (M-1))

-
Cl <10 <10
-
Br 631 000 28 800
-
I 37 100 955 000
Due to the solvation of the anion by water and methanol, the effective charge of anions has the
order of I-> Br- > Cl-. However, note that for L1, Br- binds stronger than I-. Which of the
following would be the most accurate statement for receptor L3 (X=Cl)? (Assume X…anion
interactions are the same for X=Cl, Br and I). (Hint: receptor binds anions well when the anion is
complementary to the macrocycle binding cavity)
(a) I- binding constant of (L2) > (L1) ; is always true
(b) I- binding constant of (L2) = (L3) ; is always true
(c) I- binding constant of (L2) = (L1) ; is always true
(d) I- binding constant of (L2) < (L3) ; is always true
(e) Cannot predict binding constant trend from the given information

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(45) The counteranion of the series of receptors above is PF6-. Considering receptor L3, if the
counteranion was exchanged to Br-, which of the following is most accurate? (Assume the
binding of PF6- to receptors are negligible).
(a) Binding constant of I- would increase
(b) Binding constant of I- would decrease
(c) Binding constant of I- would not change
(d) Both a and b are possible
(e) Need more information to predict the binding constants

………….END………….

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