QOI 0809 (REV)
Name___________________________________
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
1) The atomic number of boron is 5. The correct electronic configuration of boron is:
A) 1s2 2s3
B) 1s22p3
C) 1s2 2s2 2p1
D) 2s2 2p3
1)
E) 1s2 2s23s1
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
2) Atoms with the same number of protons but different numbers of neutrons are called
__________.
2)
3) The electron density of __________ orbitals has spherical symmetry.
3)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
4) Draw the shape of a 2p orbital.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
5) How many distinct p orbitals exist in the second electron shell, where n = 2?
A) 2
B) 3
C) 4
D) 5
5)
E) 6
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
6) An oxygen atom has __________ valence electrons.
6)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
7) Draw a correct Lewis structure for chloromethane, CH3 Cl.
8) Draw a correct Lewis structure for boric acid, B(OH)3 .
9) Draw a correct Lewis structure for tert-butyl alcohol, (CH3 )3COH.
10) Draw a correct Lewis structure for acetonitrile, CH3CN.
1
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
11) Which of the following are correct Lewis structures, including formal charges, for nitric acid,
HNO3 ?
11)
A) A only
B) B only
C) C only
D) both B and C
E) A, B, and C
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
12) Covalent bonds may be polar or nonpolar. What property of the atoms forming a given bond determines this?
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
13) The compound methylamine, CH3 NH2 , contains a CN bond. In this bond, which of the following
best describes the charge on the carbon atom?
A) +1
B) slightly positive
C) uncharged
D) slightly negative
E) -1
13)
14) The formal charge on oxygen in dimethyl ether, CH3 OCH3 , is:
A) +2
B) +1
C) 0
D) -1
14)
E) -2
15) The formal charge on nitrogen in the compound below is __________.
A) +2
B) +1
C) 0
D) -1
2
15)
E) -2
16) Which of the following choices represent(s) a pair of resonance forms?
A)
16)
B)
C)
D) both A and C
E) both B and C
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
17) The Lewis structure of trimethylamine is shown below. Draw the condensed structural formula which
corresponds to this Lewis structure.
18) The Lewis structure of pentane is shown below. Draw the condensed structural formula which corresponds to
this Lewis structure.
19) Draw an acceptable line-angle formula for cyclobutanol (shown below).
3
20) Draw an acceptable line-angle formula for the compound shown below.
21) Draw a correct Lewis structure for acetaldehyde, CH3 CHO.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
22) A sample of compound X is subjected to elemental analysis and the following percentages by
weight are found: 39.97% C, 6.73% H, and 53.30% O. The molecular weight of X is 90. What is the
empirical formula of X?
A) C6 HO8
B) C2 H4 O2
C) C4H10O2
D) C3 H6 O3
E) CH2 O
22)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
23) Calculate the pH of a 250 mL aqueous solution which contains 0.70 g of HCl.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
24) The pH of a 150 mL aqueous solution of 2.13 x 10-3 M HCl is:
A) -3.000
B) 3.000
C) 2.672
D) 2.130
E) none of the above
24)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
25) Calculate the pH of a 100 mL aqueous solution containing 1.80 g of KOH (MW = 56.11 g/mol).
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
26) The conjugate acid of ammonia, NH3 , is:
A) NH2 -
26)
B) NH2OH
C) NH4 +
D) none of the above
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
27) Write a completed equation for the acid-base pair shown below.
HCN + NaOH →
4
28) Write a completed equation for the acid-base pair shown below.
HCO2 H + -NH2 →
29) Consider the set of compounds, NH3 , HF, and H2 O. Rank these compounds in order of increasing acidity and
discuss your rationale.
30) Methanesulfonic acid, CH3 SO3 H, has a pKa of -7 while ethanol, CH3 CH2 OH, has a pKa of 15.9. Which is the
stronger acid and what accounts for this large difference in relative acidity?
31) Would you predict trifluoromethanesulfonic acid, CF3 SO3 H, to be a stronger or weaker acid than
methanesulfonic acid, CH3 SO3 H? Explain your reasoning.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
32) Which of the following terms comes closest to describing an electrophile?
A) anion
B) Lewis base
C) Lewis acid
D) nucleophile
E) nonpolar
32)
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
33) The element with the electronic configuration 1s2 2s22p6 3s1 is __________.
33)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
34) Which of the following compounds are covalent compounds?
A) KCl
B) CF4
C) NH3
D) both A and B
E) both B and C
34)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
35) Draw a correct Lewis structure for (CH3 )2CHCOOH.
36) Draw condensed structures for the four compounds with formula C3 H9 N.
37) Calculate the empirical and molecular formulas of the compound with molecular weight 122 and an elemental
analysis of 59.01% C, 4.97% H, 13.12% O, and 22.90% N.
38) A 0.1 M aqueous solution of an acid HA has a pH of 4.0. What is the pKa of HA?
39) Draw a proper Lewis structure for H2SO4.
5
40) Use the curved arrow formalism to show the movement of electron pairs in the following reaction.
41) Use the curved arrow formalism to indicate the movement of electron pairs in the following reaction.
42) Consider the species CH3 O- , NH2 -, and CH3 COO- . Rank these ions in order of increasing basicity, and
explain your rationale.
43) Draw the other important resonance form of:
44) Draw the important resonance forms of:
45) In the reaction below, label each reactant as a nucleophile or an electrophile.
+
BH3 + CH3 SCH3 → H3 B  S (CH3 )2
46) In the reaction below, label each reactant as a nucleophile or an electrophile.
CH3 COO- + O2 S(OCH3 )2 → CH3 COOCH3 + CH3SO4MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
47) The Ka of formic acid is 1.7 x 10-4 . The pKa of formic acid is __________.
A) 1.70
B) 4.00
C) -2.36
D) 3.77
6
47)
E) 10.38
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
48) Draw the important resonance forms for the structure shown below.
49) Draw the important resonance forms for the structure shown below.
50) Draw the important resonance forms for the structure shown below.
TRUE/FALSE. Write 'T' if the statement is true and 'F' if the statement is false.
51) In a carbon atom, the 2s and 2p orbitals are equal in energy.
51)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
52) Orbitals which are equal in energy are referred to as __________.
A) degenerate
B) polar
C) nodes
D) filled
E) nonpolar
52)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
53) Stabilization of a charged species usually results when this species can be more accurately depicted as a hybrid
of several resonance forms. Why is this the case?
TRUE/FALSE. Write 'T' if the statement is true and 'F' if the statement is false.
54) When a negatively charged species is most appropriately depicted as a hybrid of several resonance
forms, the negative charge present is considered to be rapidly moving between the resonance forms
bearing the formal negative charge.
54)
55) A node is a region of high electron density between the two atoms in a covalent bond.
55)
7
56) When filling two or more orbitals of the same energy with electrons, the electrons will go into
different orbitals rather than pair up in the same orbital.
56)
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
57) For most compounds in which a nitrogen atom bears no formal charge, the valence of this
nitrogen atom is __________.
57)
TRUE/FALSE. Write 'T' if the statement is true and 'F' if the statement is false.
58) Within a given row of the periodic table, electronegativity typically increases left to right across the
row.
58)
59) Strong bases usually contain positively charged atoms of high electronegativity and no resonance
stabilization.
59)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
60) Write a Lewis structure for a compound with the molecular formula H2 N2 .
61) One or more of the atoms in the structure shown should have nonzero formal charges. Redraw the structure
and indicate any such charges.
62) While you were up late one night studying organic chemistry, you happened to see the last 5 minutes of an
infomercial on TV. The spokesperson claimed that their brand of automobile tires were superior to all other
brands on the market because they were made by using only natural rubber, isolated from the resin of rubber
trees. How could a chemist test her claims that no petroleum products went into the manufacture of her brand
of tires?
63) One or more of the atoms in the structure shown should have nonzero formal charges. Redraw the structure
and indicate any such charges.
64) Draw the complete Lewis structure for the compound whose condensed formula is (CH3)2 CHCHO.
8
65) Compute the empirical and molecular formulas for the compound of molecular weight 180 g/mol which is
shown to contain 40.0% C and 6.7% H by elemental analysis.
66) Compute the empirical and molecular formulas for the compound of molecular weight 86 g/mol which is
shown to contain 55.8% C and 7.0% H by elemental analysis.
TRUE/FALSE. Write 'T' if the statement is true and 'F' if the statement is false.
67) True or false. When a molecule can best be represented as a series of resonance forms, each of these
forms always contributes to the same degree in the hybrid.
67)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
68) The compound phenol is shown below. Provide the structure of the conjugate base of phenol.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
69) The __________ tells us that each orbital can hold a maximum of 2 electrons.
A) aufbau principle
B) Pauli exclusion principle
C) Hund's rule principle
D) LeChatelier principle
E) uncertainty principle
69)
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
70) Draw a line-angle formula for (CH3 )2 CHCH2 CH2NH2.
70)
71) Rank the following compounds in order of increasing acidity: CH3OH, HCl, NH3 , and
CH4 .
71)
72) Rank the following compounds in order of increasing basicity: CH3O- , H2 N- , H2 O, and
NH3 .
72)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
73) In the compound sodium methoxide (NaOCH3), there is __________ bonding.
A) ionic
B) polar covalent
C) nonpolar covalent
D) a mixture of ionic and covalent
E) resonance stabilized
9
73)
74) A carbon-hydrogen bond in ethane (CH3CH3 ) is best described a __________.
74)
A) highly polar
B) essentially nonpolar
C) ionic
D) a multiple bond
E) resonance stabilized
75) When methanol (CH3OH) acts as a base, its conjugate acid is __________.
75)
A) - CH2OH
B) CH3 OC) CH4 OH
D) CH3 OH2 +
E) CH4 O+
76) Which of the following pairs of bases lists the stronger base first?
A) I- > Cl-
76)
B) H2O > HOC) HO- > H2ND) CH3 COO- > HOE) H2N- > CH3 COOSHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
77) Draw the structure of the conjugate acid of acetone (CH3COCH3 ).
77)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
78) Which of the following condensed formulas represents the same compound as the line-angle
structure shown?
A) CH3 CH2CH2 OCH2CH2 CH2 N(CH2CH2 CH3 )2
B) CH3 CH2CH2 OCH2N(CH2 CH3 )2
C) CH3 CH2OCH2 N(CH2 CH3 )2
D) CH3 CH2OCH2 N(CH2 CH2 CH3 )2
E) CH3 ON(CH3 )2
10
78)
79) The hydroxide ion (HO- ) cannot function well as which of the following?
A) a Bronsted-Lowry base
B) a Lewis base
C) a nucleophile
D) an electron-pair acceptor
E) a proton acceptor
79)
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
80) Provide the products of the following acid-base reaction.
80)
(CH3 )3NH+ + HO- →
81) Which is more acidic, HF or HI? Explain.
81)
82) Which is more acidic, methanesulfonic acid (CH3 SO3 H) or propanoic acid
82)
(CH3 CH2CO2 H)? Explain.
83) Methanol has a pKa of 15.5. Calculate its Ka.
83)
84) Provide a Lewis structure for a molecule with molecular formula CH2O2 .
84)
85) A condensed structure for acetone is CH3 COCH3 . Provide the structural formula for
85)
acetone.
86) Provide the line-angle formula for the alcohol CH3CH2 CH(OH)CH2 CH2 CH(CH3 )2.
86)
87) Assign the correct formal charge to each nitrogen atom in the following Lewis structure.
87)
88) Provide the structural formula for an aldehyde whose condensed structure is
(CH3 )3CCHO.
88)
89) Which element in the second row of the periodic table has six valence electrons and a
valence of two?
89)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
90) The electronegativity of elements on the periodic table increases going __________ a column and to
the __________ in each row.
A) up, right
B) up, left
C) down, right
D) down, left
11
90)
91) Indicate the line-angle structure that corresponds to the condensed structure,
HOCH2 C(O)CH(CH3 )2.
A)
B)
C)
91)
D)
92) Which sequence correctly ranks the indicated protons in order of increasing acidity?
A) 1 < 2 < 3
B) 2 < 3 < 1
C) 3 < 1 < 2
D) 2 < 1 < 3
92)
E) 1 < 3 < 2
93) Structures __________ , shown below, are resonance structures, and structure __________ is the
major contributor to the overall resonance hybrid.
93)
A) 2 & 4; 2
B) 1, 3 & 5; 3
C) 4 & 6; 6
D) 1, 3 & 5; 1
E) 1, 3, 4 &5; 3
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
94) Nitroamines are common functional groups found in energetic materials, such as RDX and
HMX. For the structure below, draw two other significant resonance structures, include
any formal charges, and indicate the hybridization on each nitrogen and oxygen.
94)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
95) According to the Lewis definition, which of the following may act as acids?
A) NH3
B) HCl
C) AlCl3
D) A & B
12
95)
E) A, B, & C
96) Which sequence correctly ranks the following protons in order of increasing acidity?
A) 1 < 2 < 3
B) 2 < 3 < 1
C) 3 < 1 < 2
D) 3 < 2 < 1
96)
E) 2 < 1 < 3
97) According to the following pKa values listed for a set of acids, which would lead to the strongest
conjugate base?
A) -2
B) 1
C) 7
D) 25
E) 50
13
97)
Answer Key
Testname: QOI0809T1
1) C
ID: oc6w 1-1
Diff: 1
Skill:
2) isotopes
ID: oc6w 1-2
Diff: 1
Skill:
3) s
ID: oc6w 1-3
Diff: 1
Skill:
4)
ID: oc6w 1-4
Diff: 2
Skill:
5) B
ID: oc6w 1-5
Diff: 1
Skill:
6) 6
ID: oc6w 1-6
Diff: 1
Skill:
7)
ID: oc6w 1-7
Diff: 1
Skill:
8)
or
ID: oc6w 1-8
Diff: 2
Skill:
14
Answer Key
Testname: QOI0809T1
9)
ID: oc6w 1-9
Diff: 2
Skill:
10)
ID: oc6w 1-10
Diff: 2
Skill:
11) B
ID: oc6w 1-11
Diff: 3
Skill:
12) Electronegativity
ID: oc6w 1-12
Diff: 2
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13) B
ID: oc6w 1-13
Diff: 3
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14) C
ID: oc6w 1-14
Diff: 1
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15) B
ID: oc6w 1-15
Diff: 2
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16) E
ID: oc6w 1-16
Diff: 3
Skill:
17) (CH3 )3N
ID: oc6w 1-17
Diff: 1
Skill:
15
Answer Key
Testname: QOI0809T1
18) CH3 (CH2)3 CH3
ID: oc6w 1-18
Diff: 1
Skill:
19)
ID: oc6w 1-19
Diff: 2
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20)
ID: oc6w 1-20
Diff: 2
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21)
ID: oc6w 1-21
Diff: 2
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22) E
ID: oc6w 1-22
Diff: 3
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23) 1.11
ID: oc6w 1-23
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24) C
ID: oc6w 1-24
Diff: 2
Skill:
25) 13.506
ID: oc6w 1-25
Diff: 3
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26) C
ID: oc6w 1-26
Diff: 2
Skill:
16
Answer Key
Testname: QOI0809T1
27) HCN + NaOH → NaCN + H2 O
ID: oc6w 1-27
Diff: 2
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28) HCO2 H + -NH2 → HCO2 - + NH3
ID: oc6w 1-28
Diff: 2
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29) NH3 < H2O < HF
When determining relative acidity, it is often useful to look at the relative basicity of the conjugate bases. The stronger
the acid, the weaker (more stable, less reactive) the conjugate base. In this case, one would look at the relative basicity
of F- , OH- , and NH2 -. The relative strengths of these species can be gauged based on the electronegativity of the
charged atom in each. Since fluorine is the most electronegative, F- is the most stable, least reactive base in the group.
This means that its conjugate acid, HF, is the strongest.
ID: oc6w 1-29
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Skill:
30) Methanesulfonic acid is the stronger acid. The lower the pKa, the stronger the acid. A lower pKa is associated with a
larger Ka which signifies greater dissociation. The large relative difference in acidity in this case can be most easily
seen by gauging the relative basicities of the conjugate bases. The weaker the base, the stronger the corresponding
conjugate acid. Methanesulfonate, CH3SO3- , is considerably stabilized by resonance delocalization which is not found
in ethoxide, CH3 CH2 O- . This effect greatly reduces the basicity of methanesulfonate relative to ethoxide.
ID: oc6w 1-30
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Skill:
31) Trifluoromethanesulfonic acid is a stronger acid. Compare the strengths of the conjugate bases and remember that the
weaker the base, the stronger the conjugate acid. Both bases are stabilized by resonance, but in the case of the trifluoro
derivative, the presence of the highly electronegative fluorine atoms serves to delocalize the negative charge to an even
greater extent. This additional delocalization makes trifluoromethanesulfonate a weaker base.
ID: oc6w 1-31
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32) C
ID: oc6w 1-32
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Skill:
33) sodium
ID: oc6w 1-33
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34) E
ID: oc6w 1-34
Diff: 2
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17
Answer Key
Testname: QOI0809T1
35)
ID: oc6w 1-35
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36) CH3 CH2CH2 NH2
CH3 CH2NHCH3
(CH3 )2CHNH2
(CH3 )3N
ID: oc6w 1-36
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37) Empirical and molecular formulas are the same: C6 H6 N2 O.
ID: oc6w 1-37
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38) 7
ID: oc6w 1-38
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39)
ID: oc6w 1-39
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40)
ID: oc6w 1-40
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18
Answer Key
Testname: QOI0809T1
41)
ID: oc6w 1-41
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Skill:
42) CH3 COO- < CH3 O- < NH2 The first factor to consider is the nature of the atom which bears the negative charge. The more electronegative the
atom that bears the negative charge, the more stable the anion. Stable anions are less reactive and are hence weaker
bases. Since O is more electronegative than N, the NH2 - is the strongest base in the set. In the remaining two species,
the negative charge is on the O, but in the case of CH3COO - , the negative charge is also delocalized by resonance.
ID: oc6w 1-42
Diff: 3
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43)
ID: oc6w 1-43
Diff: 3
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44)
ID: oc6w 1-44
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45) BH3, electrophile
CH3 SCH3 , nucleophile
ID: oc6w 1-45
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46) CH3 COO- , nucleophile
O2 S(OCH3 )2 , electrophile
ID: oc6w 1-46
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47) D
ID: oc6w 1-47
Diff: 2
Skill:
19
Answer Key
Testname: QOI0809T1
48)
ID: oc6w 1-48
Diff: 3
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49)
ID: oc6w 1-49
Diff: 3
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50)
ID: oc6w 1-50
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51) FALSE
ID: oc6w 1-51
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52) A
ID: oc6w 1-52
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53) Stabilization results from delocalization of charge.
ID: oc6w 1-53
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54) FALSE
ID: oc6w 1-54
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55) FALSE
ID: oc6w 1-55
Diff: 1
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20
Answer Key
Testname: QOI0809T1
56) TRUE
ID: oc6w 1-56
Diff: 1
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57) 3
ID: oc6w 1-57
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58) TRUE
ID: oc6w 1-58
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59) FALSE
ID: oc6w 1-59
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60)
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61)
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62) Compounds synthesized from petroleum products have a lower content of 14C. Plant-derived compounds are recently
synthesized from CO2 in the air and have a higher 14C content.
ID: oc6w 1-62
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21
Answer Key
Testname: QOI0809T1
63)
ID: oc6w 1-63
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64)
ID: oc6w 1-64
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65) The empirical formula is CH2 O and the molecular formula is C6H12O6 .
ID: oc6w 1-65
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66) The empirical formula is C2 H3 O and the molecular formula is C4H6 O2 .
ID: oc6w 1-66
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67) FALSE
ID: oc6w 1-67
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68)
ID: oc6w 1-68
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69) B
ID: oc6w 1-69
Diff: 1
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22
Answer Key
Testname: QOI0809T1
70)
ID: oc6w 1-70
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71) CH4 < NH3 < CH3 OH < HCl
ID: oc6w 1-71
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72) H2O < NH3 < CH3 O- < H2 NID: oc6w 1-72
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73) D
ID: oc6w 1-73
Diff: 1
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74) B
ID: oc6w 1-74
Diff: 1
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75) D
ID: oc6w 1-75
Diff: 2
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76) E
ID: oc6w 1-76
Diff: 2
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77)
ID: oc6w 1-77
Diff: 2
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78) C
ID: oc6w 1-78
Diff: 2
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79) D
ID: oc6w 1-79
Diff: 1
Skill:
23
Answer Key
Testname: QOI0809T1
80) (CH3 )3N + H2 O
ID: oc6w 1-80
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81) HI is more acidic. As a conjugate base I- is more stable than F-. The large size of the I- ion allows the extra negative
charge to be spread out in a large volume of space.
ID: oc6w 1-81
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82) Methansulfonic acid is considerably more acidic. The methanesulfonate ion is much more stable than the propanoate
ion. Both of these conjugate bases are stabilized by resonance delocalization of the negative charge, but this
delocalization is more extensive in the sulfonate.
ID: oc6w 1-82
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83) 3.2 x 10 -16
ID: oc6w 1-83
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84)
ID: oc6w 1-84
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85)
ID: oc6w 1-85
Diff: 2
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86)
ID: oc6w 1-86
Diff: 2
Skill:
24
Answer Key
Testname: QOI0809T1
87)
ID: oc6w 1-87
Diff: 2
Skill:
88)
ID: oc6w 1-88
Diff: 2
Skill:
89) oxygen
ID: oc6w 1-89
Diff: 1
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90) A
ID: oc6w 1-90
Diff: 1
Skill: 1
91) A
ID: oc6w 1-91
Diff: 2
Skill:
92) C
ID: oc6w 1-92
Diff: 3
Skill:
93) B
ID: oc6w 1-93
Diff: 3
Skill:
94) All nitrogen and oxygen atoms are sp2 hybridized.
ID: oc6w 1-94
Diff: 3
Skill:
25
Answer Key
Testname: QOI0809T1
95) E
ID: oc6w 1-95
Diff: 2
Skill:
96) D
ID: oc6w 1-96
Diff: 3
Skill:
97) E
ID: oc6w 1-97
Diff: 2
Skill:
26
QOI 0809 (REV)
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