Mock USNCO Part I

Problem writers: Harrison Wang, Alex Liu

Test solvers: Steven Liu, Ben Nguyen

Rules: You have 2 hours and 30 minutes to complete this 60 question multiple choice test. You may not use the Internet,
textbooks, notes, nor any other resources outside of this document to aid you in taking this test. You are not allowed to
use a programmable calculator nor equation solvers. You may only use a nonprogrammable calculator. Please submit
your answers here: https://goo.gl/forms/FES7wc1pLGi66FtU2. Cover page property of ACS. Good luck!

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1. You obtain a single molecule of a polymer with 4. You later find that you actually made only 13.2
mass of 771 u. What is a possible structure of the grams of CCl4 , and the rest is a mixture of un-
polymer? wanted carbon chlorides and unreacted starting
material. What is your actual percent yield?
(A) n = 10,
(A) 0.65% (B) 1.72%
(C) 2.15% (D) 8.58%

The following information will be used for questions

5–7. You have three unknown solutions labeled A
(B) n = 20, through C. A is a colorless solution that burns yellow
in a flame test and is highly basic. B is colorless. C
is bright orange. A pungent-smelling gas is produced
upon mixing A and B. A deep blue solution results
from mixing B with C and then adding starch. A
yellow solution results from mixing A and C.

(C) n = 5, 5. Which solute is most likely to be dissolved in A?

(A) KNO2
(B) CaCO3
(C) KOH contaminated with NaOH

(D) n = 10, (D) Ru(CHC6 H5 )(PPh3 )2 Cl2

6. Which solute is most likely to be dissolved in B?

(A) Na2 S (B) K2 S (C) NH4 Cl (D) NH4 I

7. Which solute is most likely to be dissolved in C?

2. You burn a sample of 1 mol of silane (SiH4 ) in air. (A) Na2 Cr2 O7 (B) Hg(CH2 CH3 )2
Assuming complete combustion, what is the total (C) FeCl3 (D) CoCl3 · 6 NH3
mass of the products?
8. To isolate purified benzoic acid (C6 H5 COOH,
(A) 32.1 g (B) 64.1 g
mildly soluble in water, boiling point = 249◦
(C) 96.1 g (D) 128.1 g C), from an aqueous solution of sodium benzoate
(C6 H5 OO− Na+ , soluble in water, melting point =
The following information will be used for questions 450◦ C), which procedure is best?
3–4. You react 5 mol of Cl2 with 1 mol of CH4 in
your UV reaction chamber. The possible reactions (A) Evaporate off the water.
are as follows:
(B) Add HCl. Filter off the water. Recrystallize
Cl2 + CH4 −−→ HCl + CH3 Cl the collected solid and filter again.

2 Cl2 + CH4 −−→ 2 HCl + CH2 Cl2 (C) React the sodium benzoate with CuCl2(aq) ,
forming copper benzoate Cu(C6 H5 OO− )2 . Evapo-
3 Cl2 + CH4 −−→ 3 HCl + CHCl3
rate off the water and then add HCl(g) in a closed
4 Cl2 + CH4 −−→ 4 HCl + CCl4 chamber. Dissolve the product in a chilled solution
of nitric acid, and evaporate off the water again.
3. After titrating the sample, you find that 2.96 mol of
HCl was produced. Given this information, what (D) Add the solution to a round-bottom flask
is the highest possible percent yield of CCl4 ? placed directly above a heating mantle. Distill.
Collect the fraction around 250◦ C.
(A) 59.2% (B) 63.8%
(C) 69.5% (D) 74.0%

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 9. The Kjeldahl method utilizes which element's
oxoacid to oxidize organic compounds while reduc-
ing nitrogen in those compounds to ammonia?
(A) Nitrogen (B) Sulfur
(C) Chlorine (D) Tungsten
The following information will be used for questions
10–12. You run a spectrophotometric titration of a
20.00 mL solution of KMnO4 through addition of a
standardized solution of 0.500 M Na2 C2 O4 . During
the titration, you plot the absorbance of the solution
at 525 nm (A) as a function of volume of Na2 C2 O4
added (V). Although you forgot the molar absorptiv-
ity of KMnO4 at 525 nm, you know that it is posi-
tive, and you find that the equivalence point occurs
at 19.88 mL of Na2 C2 O4 added. Tick marks on the
x axis represent increments of 10.00 mL, while the y
axis is linearly incremented. Assume that the molar
absorptivity of all other species at 525 nm is zero.
10. What is the expected shape of a titration curve for
this titration?
(A)
(B)
(C)
(D)
11. What is the concentration of your KMnO4 solution
in question 10?
(A) 0.166 M (B) 0.199 M
(C) 0.249 M (D) 0.497 M
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12. Given that you can calculate all the concentrations
of MnO4 − at each stage of the titration, which er-
ror would lead to the least experimental deviation
from accurate calculations?
(A) While loading your sample, you pick up the
cuvette without gloves.
(B) The monochromator in your spectrophotome-
ter isnt selective enough.
(C) You wash your gloved hands, and some wa-
ter droplets with a total volume greater than 5 mL
drop from your glove into the sample.
(D) There is K+ contaminant in the Na2 C2 O4 so-
lution.
13. When copper metal is dissolved in fuming nitric
acid, a brown gas is formed. The brown gas is im-
mediately collected and placed in a chamber at a
temperature of 10 K, causing it to turn colorless.
What is the ratio of molar masses of the brown gas
to the colorless gas?
(A) 1:1 (B) 1:2 (C) 2:1 (D) 1:3
14. A Carnot cycle is set up with the hot reservoir
having a temperature of 250◦ C and the cold reser-
voir having a temperature of 70◦ C. Assuming ideal
conditions, what is the efficiency of this cycle?
(A) 28% (B) 34% (C) 72% (D) 100%
15. Consider two 5.0 L balloons each filled with
equimolar amounts of H2 and O2 gas at STP. Let
n1 be the maximum theoretical amount of water
vapor produced from the reaction of the first bal-
loon's contents. Allow the second balloon's con-
tents to effuse out of the balloon until its volume
is 2.5 L. Assume that the initial effusion rates stay
constant throughout. Define n2 analogously to n1
for the second balloon. What is the ratio of n1 to
n2 ?
(A) 2 (B) 4 (C) 5 (D) 8
16. In adiabatic processes, no heat is added or re-
moved from the system. If the temperature of a
gas, in Kelvin, is doubled during an adiabatic com-
pression, which of the following statements can be
true?
(A) The volume increases by a factor ≤ 2
(B) The volume increases by a factor > 2
(C) The volume decreases by a factor ≤ 2
(D) The volume decreases by a factor > 2
17. Which is true about the phase diagram for water
(assume that there is only one form of ice)?
(A) Solid water can exist at temperatures larger
than 100◦ C
(B) The triple point exists at a temperature
greater than 0◦ C
(C) Solid water is denser than liquid water at any
particular pressure
22. You have a beaker with 10.00 g of vegetable oil,
a beaker with 10.00 g of water, and a beaker
with 10.00 g of ethanol. You heat the water to
42.22◦ C and you chill the ethanol to 2.222◦ C. Your
vegetable oil is at room temperature of 22.22◦ C.
What is the equilibrium temperature of all three
substances when they are mixed? The specific
heat capacities are given in the table below.
Substance Specific heat capacity (J · g−1 ·K−1 )

(D) At absolute zero, water can be in liquid or Vegetable oil 2.000

vapor form Water 4.000

18. In the unit cell of fluorite, or calcium fluoride, cal- Ethanol 2.000
cium ions make up an fcc lattice, while fluoride
ions fill the holes. What kind of holes are they, (A) 17.22◦ C (B) 22.22◦ C
and what fraction are filled by fluoride ions?
(C) 27.22◦ C (D) 32.22◦ C
(A) Tetrahedral, half are filled
23. What signs are the ∆H and ∆S of the process of
(B) Tetrahedral, all are filled mixing water and ethanol together to form an ideal
(C) Octahedral, half are filled solution?

(D) Octahedral, all are filled (A) ∆H = 0, ∆S is positive

(B) ∆H is negative, ∆S is positive
19. Which of the following solutions has the lowest
freezing point? (C) ∆H is positive, ∆S is positive
(D) ∆H is negative, ∆S is negative
(A) .3 M MgCl2
(B) .4 M NaCl 24. Which of the following is true for the melting of
solid hexane?
(C) .6 M Cl3 CCOOH
(D) .7 M sucrose I. The molar volume change is negative.
II. Assuming a constant molar volume change,
this integrated Clausius-Clapeyron equation and
20. A hypothetical enzyme can isomerize C5 H10 (pent-
that of the boiling of liquid hexane are in the same
1-ene) to C5 H10 (cyclopentane). What is the stan-
form.
dard entropy of this reaction, in J·mol−1 ·K−1 ?
(A) I only (B) II only
(A) –579 (B) –57.9 (C) 57.9 (D) 579
(C) Both I and II (D) Neither I nor II
21. The change in entropy of a solid or a liquid as a
T 25. Which of the following processes are exothermic?
function of temperature is ∆S = C ln Tfi , where
C is the heat capacity, Tf is the final temper-
ature, and Ti is the initial temperature. What I. H2 O (l) −−→ H2 O (g)
is the standard change in entropy of the reaction II. CaO (s) + H2 O (g) −−→ Ca(OH)2 (s)
H2 O (s) −−→ H2 O (l) at 100.5 K? The specific heat III. CaO (s) −−→ Ca2+ (g) + O2− (g)
capacity of ice is 40 J·mol−1 · K−1 , the specific heat
capacity of water is 75 J mol−1 ·K−1 , and the en- (A) II only
tropy of melting is 22 J mol−1 ·K−1 . (B) I and II only
(A) 13 J·mol−1 ·K−1 (C) I and III only
(B) 18 J·mol−1 ·K−1 (D) I, II, and III
(C) –13 J·mol−1 ·K−1
(D) –18 J·mol−1 ·K−1
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26. A free neutron is unstable and decays into a pro-
ton, electron, and antineutrinos. After precisely 60
minutes, a sample of 1.0000 · 1010 neutrons emit-
ted 9.8305 · 109 electrons. What is the half life of
a neutron?
(A) 10.2 min
(B) 10.4 min
(C) 10.6 min
30. In a constant-pressure flask, V2 O5 spontaneously
(D) 10.8 min
27. A certain reactant of a decomposition reaction, X,
has the following concentrations at the given times:
29. The pre-exponential factor in the Arrhenius equa-
tion does not depend on which of the following?
(A) Collision frequency
(B) Reactant molecule size
(C) Reactant molecule mass
(D) Reactant concentration
catalyzes the reaction between SO2 and O2 to form
SO3 . Assume that the V2 O5 takes up no volume.
Which of the following would increase the equilib-
rium yield of SO3 ?

I. Increasing pressure
Time (s) [X] (M) II. Increasing temperature
0.0 1.800 · 10−1 (A) Only I (B) Only II
−1
0.1 1.7205 · 10 (C) Both I and II (D) Neither I nor II
0.2 1.637 · 10−1
31. A solution of 0.005 molal benzoic acid, a weak
0.3 1.549 · 10−1 monoprotic acid, boils at a temperature 2.82964 ·
0.4 1.456 · 10−1 10−3 K higher than pure water. What is the Ka
of benzoic acid? The boiling point elevation con-
0.5 1.356 · 10−1 stant is equal to 0.512 K·kg·mol−1 . Assume mo-
lality and molarity are equivalent measurements of
1.0 6.633 · 10−2
concentration and that the solution does not ex-
1.1 4.000 · 10−2 pand upon heating.

1.5 0 (A) 1.0 · 10−4 (B) 9.2 · 10−5

(C) 7.8 · 10−5 (D) 6.2 · 10−5
To the nearest hundredth, what was the earliest
time that the reactant completely disappeared?
The following information will be used for questions
32–33. Acetic acid (C2 H4 O2 ): pKa = 4.76. Pro-
(A) 1.13 s
tonated acetic acid (C2 H5 O2 + ): pKa = –6.4. HCl:
(B) 1.16 s pKa = –6.0. Density of glacial acetic acid: 1.05 g
·mL−1 .
(C) 1.19 s
(D) There is always reactant present. 32. Calculate Kx , where Kx = [C2 H5 O2 + ][C2 H3 O2 − ]
(this is analogous to Kw for water).

28. At 25◦ C, a hypothetical reaction A −−→ B has a (A) 1.0 · 10−14 (B) 6.9 · 10−12
rate constant of 3.14 · 105 s−1 . At 90◦ , the same re-
action had a rate constant of 2.72 · 103 s−1 . Which (C) 3.2 · 10−11 (D) 5.2 · 10−9
of the following statements is accurate?
33. Calculate the concentration of C2 H5 O2 + in a 1 M
(A) The activation energy of the reaction is +65.7 solution of HCl with glacial acetic acid as the sol-
kJ·mol−1 vent. You can assume that glacial acetic acid is
100% acetic acid.
(B) The activation energy of the reaction is –65.7
kJ·mol−1 (A) 0.46 M (B) 0.88 M

(C) The activation energy of the reaction is –52.3 (C) 0.92 M (D) 1.0 M
kJ·mol−1

(D) This is not possible

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34. You have a .1000 M freshly prepared solution of a 39. What is the primary reason one might use a refer-
monoprotic acid, HA, but unfortunately you forgot ence AgCl electrode over a standard calomel elec-
which acid you used! You titrate it with .1000 M trode?
NaOH to determine the Ka value of the acid, and
at the equivalence point you measure the pH to be (A) An AgCl electrode is less toxic.
9.23. Unfortunately, you also forgot how much of
(B) A saturated AgCl electrode has a higher re-
the solution you titrated! What is the Ka value of
duction potential, preventing the net reaction to
the acid?
go to completion.
(A) 1.73 · 10−6
(C) An AgCl electrode is more accurate.
(B) 3.47 · 10−6
(D) Commercial AgCl electrodes are plugged with
(C) 9.34 · 10−5 Vycor® , which makes the electrode less conduc-
tive.
(D) Cannot tell based on the data given
40. Based on the following reactions and data below,
35. You have six different monoprotic acids HAi for what is the Ksp of Hg2 Cl2 at 298 K?
i = 1, 2, 3, 4, 5, 6, that have corresponding acid dis-
sociation constants Ki < 10−9 . You also have six Hg2 Cl2(s) + 2 e− −−→ 2 Hg + 2 Cl− E00 = 0.244 V
beakers such that in beaker i, 1.00 L of HAi is dis-
Hg2 2+ + 2 e− −−→ 2 Hg E10 = 0.797 V
solved. Furthermore, you find that the sum of the
equilibrium concentration of H+ of all six beakers,
(A) 4.2 · 10−10 (B) 1.6 · 10−18
P6 +
i=1 [H ]i , is 0.00020 M. P6
What is the minimum
possible value, in M2 , of i=1 [HAi ]·Ki ? (C) 2.0 · 10−19 (D) 5.4 · 10−44
(A) 0.0020 (B) 6.7 · 10−6
41. What is the absolute value of the net Gibbs free en-
(C) 5.4 · 10−8 (D) 6.7 · 10−9 ergy expenditure to oxidize 0.5 mol of ethanol at
standard state, given that the oxidation potential
36. 1 mol of gaseous acetic acid is added to a stop- of ethanol is 0.197 V and two electrons are removed
pered flask at a temperature of 298 K and is al- in the reaction?
lowed to dimerize. If the total pressure after dimer-
ization is 0.300 atm, how many moles of hydrogen (A) 4.3 kJ (B) 9.5 kJ (C) 19 kJ (D) 38 kJ
bonds are formed between molecules of acetic acid?
Assume acetic acid only forms hydrogen bonds in 42. Which gaseous ion has the most unpaired elec-
the dimerized form. The equilibrium constant of trons?
dimerization at 298 K is 144. (A) V3+ (B) Fe3+ (C) Co2+ (D) U4+
(A) 0.859 mol (B) 0.924 mol
43. Rank the ionization energies of Si, P, and S in in-
(C) 0.948 mol (D) 1.72 mol creasing order.

37. The standard reduction potentials of Fe3+ and (A) Si, P, S (B) S, P, Si
Fe2+ are –0.02 V and –0.41 V, respectively. What (C) Si, S, P (D) S, Si, P
◦
is Ecell for the reaction Fe3+ + e− −−→ Fe2+ ?
44. Zirconyl chloride, [Zr4 (OH)8 (H2 O)16 ]Cl8 (H2 O)12 ,
(A) –0.39 V (B) +0.39 V
is dissolved in water. What is the color of the re-
(C) +0.76 V (D) +1.19 V sulting solution?

(A) colorless
38. You react two moles of Fe(OH)3 with three moles
of OCl− under basic conditions, forming five moles (B) clear
of water, two moles of a light purple iron complex,
and three moles of Cl− ions. In which oxidation (C) yellow
state is the iron in the iron complex? (D) Zirconyl chloride is insoluble.
(A) II (B) IV (C) V (D) VI
45. How many minima does the 3s orbital radial dis-
tribution function 4πr2 |Ψ(r)|2 have?

(A) 0 (B) 1 (C) 2 (D) 3

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46. Electrons in the hydrogen atom from higher en- 55. Into which initial product does the liver oxidize
ergy levels emit wavelengths of light corresponding ethanol?
to the Paschen series when they transition to the
energy level n = 3. The transition from n = 4 (A) Ethane (B) Ethene
to n = 3 emits a photon of wavelength 1875 nm. (C) Acetic Acid (D) Acetaldehyde
What is the smallest wavelength of light emitted
in the Paschen series?
56. Which of the following cannot be the molecular
(A) 1875 nm (B) 820.3 nm formula of an alkene?

(C) 625.0 nm (D) 208.3 nm (A) CH2 (B) C2 H4 (C) C4 H6 (D) C6 H8

47. Which atom or molecule is IR active? 57. On a physiological level, why is drinking ethanol
an antidote for methanol poisoning?
(A) He (B) 1H2 (C) 2H2 (D) 1H2 O
(A) Ethanol reacts with methanol to form a bio-
48. Which compound does not exist? logically inactive product.

(A) KrF6 (B) XeF6 (c) SF6 (D) UF6 (B) Ethanol restores the damaged optic nerves as
a result of formic acid destruction.
49. What is the bond order of the Se-O bond in the
selenate ion? (C) Ethanol competitively inhibits the active site
of alcohol dehydrogenase, the enzyme that both
4 3 oxidizes ethanol and methanol.
(A) 1 (B) 3 (C) 2 (D) 2
(D) Ethanol competitively inhibits the active site
of aldehyde dehydrogenase, which is not the en-
50. zyme that oxidizes ethanol, but is the enzyme that
oxidizes formaldehyde.

The structure of sodium thiosulfate is shown

above. Two mol of thiosulfate is easily oxidized to
58.
one mol of tetrathionate anion S4 O6 2− . How many
sulfur-sulfur bonds are present in tetrathionate?

(A) 0 (B) 2 (C) 3 (D) 4

In the reaction above, what type of mechanism is
undergone in the halogenation of toluene to benzyl
51. Which metal, when reacted with hydrochloric acid,
chloride?
would produce bubbling at the fastest rate?

(A) Na (B) Mg (C) K (D) Ca (A) anchimeric assistance

(B) electrophilic aromatic substitution
52. Grubbs catalyst is used for olefin metathesis and
has the formula RuR(PPh3 )2 Cl2 , where R repre- (C) free radical
sents a carbene ligand. What is the bond order (D) nucleophilic aromatic substitution
of the bond between the Ru atom and the carbon
atom in the R group?

(A) 1 (B) 2 (C) 3 (D) 4

59.
53. What is the hybridization of the nitrogen in
dimethylformamide (HCON(CH3 )2 )?

(A) sp (B) sp2 (C) sp3 (D) sp3 d

54. How many distinct molecules with formula C3 H6 O
exist? Include tautomers in your count. Possible
functionalities include, but are not limited to car-
bonyls, ethers, and alcohols.
The structure of [18]annulene is shown above.
What is the cause of the relatively low chemical
shift in the 1 H NMR of the inner hydrogens and
relatively high chemical shift of the outer hydro-
gens of [18]annulene?

(A) 8 (B) 9 (C) 10 (D) 11 (A) Ring current

7
(B) Nonzero aromatic quadrupole moment spectrum

(C) High acidity of inner protons compared to

outer protons 60. How many electrons are transferred in the re-
duction of 3 molecules of 1,4–benzoquinone to
(D) Computational chemists have shown that benzene–1,4–diol?
[18]annulene cannot exist even in theory, and
therefore it is impossible to calculate its 1 H NMR (A) 3 (B) 4.5 (C) 6 (D) 7.5