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A) I
B) II
C) neither
Ans: B
OH
II
A) I
B) II
C) neither
Ans: A
OH
II
II
HSO4
A) I
B) II
C) neither
Ans: A
Topic: Introduction to Brnsted-Lowry Acids and Bases
Section: 3.1
Difficulty Level: Easy
7. For the following reaction, which reactant functions as a base?
H2SO4
I
II
O
H
A) I
B) II
C) neither
Ans: B
Topic: Introduction to Brnsted-Lowry Acids and Bases
Section: 3.1
Difficulty Level: Easy
HSO4
Cl
H
OH
II
Cl
A) I
B) II
C) neither
Ans: B
Topic: Introduction to Brnsted-Lowry Acids and Bases
Section: 3.1
Difficulty Level: Medium
9.
A)
B)
C)
D)
E)
Section: 3.1
Difficulty Level: Easy
12. In a Brnsted-Lowry acid-base reaction the product(s) is (are) a _______.
Ans: conjugate acid-conjugate base pair
Topic: Introduction to Brnsted-Lowry Acids and Bases
Section: 3.1
Difficulty Level: Easy
13.
A)
B)
C)
D)
E)
16.
A)
B)
C)
D)
E)
Ans:
OH
Ans:
Ans:
H
O
I
I
II
III
IV
Both I & IV
Ans: D
II
CH3CH2S Na + H2O
IV
III
I
II
III
IV
Both II & III
Ans: C
II
CH3CH2S Na + H2O
IV
III
A)
B)
C)
D)
E)
N
H
IV
III
II
+ CH3CH3 + Li
I
II
III
IV
Both I & IV
Ans: D
A)
B)
C)
D)
E)
N
H
III
II
+ CH3CH3 + Li
IV
I
II
III
IV
Both I & III
Ans: C
base
CH3CH2S Na + H2O
CH3CH2S Na + H2O
conjugate base
conjugate acid
30. For the following reaction label the acid, base, conjugate acid and conjugate base.
+ CH3CH2 Li
+ CH3CH3 + Li
N
H
Ans:
+ CH3CH2Li
+ CH3CH3
N
H
+ Li
base
acid
conjugate acid
conjugate base
Na
+ H2O
Ans:
+ NaOH
acid
base
Na
conjugate base
+ H2O
conjugate acid
+ Na OH
S Na
+ H2O
Ans:
H
S
+ Na OH
S Na
+ H2O
Section: 3.2
Difficulty Level: Easy
34. Provide a curved arrow mechanism for the following acid-base reaction.
+ Na NH2
+ NH3
Na
Ans:
+ Na NH2
Na
+ NH3
H +
NH2
H +
NH3
Ans:
H
N
H +
NH2
H +
NH3
Ans:
O
H
acid
+ Na OH
base
+ H2O + Na
37. Identify the acid and the base and provide a curved arrow mechanism for the following
reaction.
O
+ NH3
+ NaNH2
Na
Ans:
+ NH3
+ NaNH2
Acid
Na
Base
+ H2O
+ NaOH
Ans:
O
H
+ Na H
O Na
+ H2
40. For the following reaction mechanism, identify the error, if any and describe the
modification necessary by drawing the correct mechanism.
+ Na NH2
Na
+ NH3
Ans: There is only one arrow and it is going in the wrong direction. The tail of the
curved arrow is placed on the hydrogen atom. The curved arrow represents motion
of electrons and not the motion of atoms. The curved arrow must start from the
base (high electron density) and should go to the proton on the acid (low electron
density)
+ Na NH2
Na
+ NH3
O
H
Br
+ NaBr
O Na
OH
Ans: The first arrow from the lone pair of oxygen atom is correct, but the second arrow
is incorrect. The tail of the arrow is placed on the proton. The second curved
arrow must start from the HBr bond and should go to the bromine atom on the
acid.
O
O
H
Br
O Na
+ NaBr
OH
Ans:
+ Na OH
Na
O
+ H2O
Ans:
Na
+ NH3
+ H2O
II.
I.
H3O
Keq=
H2O
Keq=
H3O
IV.
III.
Keq=
Keq=
H3O
A)
B)
C)
D)
E)
H2O
H
O
I
II
III
IV
Both II & III
Ans: C
OH
A)
B)
C)
D)
E)
II
III
I
II
III
IV
None of these
Ans: B
NH2
IV
OH
A)
B)
C)
D)
E)
NH2
II
IV
III
I
II
III
IV
None of these
Ans: D
OH
NH2
NH2
A)
B)
C)
D)
E)
II
III
I
II
III
IV
All of these
Ans: A
IV
OH
NH2
NH2
A)
B)
C)
D)
E)
II
III
IV
I
II
III
IV
All of these
Ans: C
A)
B)
C)
D)
E)
II
III
I
II
III
IV
All of these
Ans: D
IV
N
H
N
H
Ans:
O
H
H
N
H
N
H
CH2
H
H
CH2
C
C
Ans:
H
C
C
N
H
H
52. For the following acid-base reaction, predict which side the equilibrium is favored.
+ NaOH
+ H2O
+ H2O
+ H3O
H
N
O
H
O
N
H
55. For the following acid-base reaction, predict which side the equilibrium is favored.
O
Li
+
Li
II
Ans: H(I) is more acidic as the sulfur atom in the conjugate base has larger atomic size
than the oxygen, which allows for spreading of charge over a larger volume of
space. This results in more stable anion and a weak conjugate base.
Topic: Brnsted-Lowry Acid: Qualitative Perspective
Section: 3.4
Difficulty Level: Hard
61. Rank the following protons in decreasing order (most to least) of acidity.
OH III
II
I H
A)
B)
C)
D)
E)
II>III>I
I>II>III
III>I>II
III>II>I
None of these
Ans: D
OH
OH
A)
B)
C)
D)
II
I
II
III
IV
Ans: A
IV
III
A)
B)
C)
D)
I
II
III
IV
Ans: D
II
III
IV
II H
III H
A)
B)
C)
D)
E)
II>I>III
II>III>I
I>III>II
I>II>III
III>II>I
Ans: D
II
II H
III H
Ans: H-I is most acidic because the conjugate base is resonance stabilized. The
negative charge is delocalized over four atoms, one oxygen atom and three carbon
atoms.
Topic: Brnsted-Lowry Acid: Qualitative Perspective
Section: 3.4
Difficulty Level: Easy
67. Which of the following compounds is most acidic?
O
OH
A)
B)
C)
D)
I
II
III
IV
Ans: B
OH
F
II
OH
I
III
OH
Br
IV
F
OH
F
A)
B)
C)
D)
OH
OH
Cl
II
I
II
III
IV
Ans: A
OH
III
Br
IV
OH
OH
F
A)
B)
C)
D)
Cl
OH
II
OH
Br
III
IV
I
II
III
IV
Ans: B
OH
A)
B)
C)
D)
Cl
I
II
III
IV
Ans: D
OH
OH
II
Cl
III
Cl
OH
F
IV
Br
Br
OH
Br
A)
B)
C)
D)
E)
OH
OH
II
Br
Br III
III>II>IV>I
II>IV>III>II
IV>III>II>I
IV>II>III>I
III>IV>II>I
Ans: E
I H
S
O
H
O
A)
B)
C)
D)
E)
IV
O
H
III
I
II
III
IV
All of these
Ans: D
Br
OH
Br
IV
CF3
II H
N
H
ethanol
Phenol
II
Ans: Compound I is more acidic. The conjugate base of both compounds is resonance
stabilized. The conjugate base of I has negative charge on more electronegative
oxygen atom, resulting in a more stable conjugate base.
Topic: Brnsted-Lowry Acid: Qualitative Perspective
Section: 3.4
Difficulty Level: Hard
76. Aspartic acid, an amino acid, has the following structure. Circle the most acidic proton
in aspartic acid. Explain your choice.
H
O
H
H
N
H
O
H
Ans:
H
O
O
H
H
N
H
O
H
The conjugate base is stabilized by the inductive effect of the adjacent nitrogen
atom.
Topic: Position of Equilibrium and Choice of Reagents
Section: 3.5
Difficulty Level: Easy
77. For the following acid-base reaction, predict which side the equilibrium is favored.
+
F3C
OH
OH
+
F3C
79. For the following acid-base reaction, predict which side the equilibrium is favored.
+
SH
SH
82. For the following acid-base reaction, predict which side the equilibrium is favored.
Explain why.
+
F3C
OH
OH
+
F3C
A) yes
B) no
Ans: B
Topic: Position of Equilibrium and Choice of Reagents
Section: 3.5
Difficulty Level: Easy
85. Determine if H2O is a suitable reagent to protonate the following compound.
O
H
S
O
A) yes
B) no
Ans: B
Ans: Yes.
The conjugate base of water has negative charge on more electronegative oxygen
atom, making it more stable.
Topic: Position of Equilibrium and Choice of Reagents
Section: 3.5
Difficulty Level: Medium
87. Determine if H2O is a suitable reagent to protonate the following compound. Explain
why.
O
Ans: No.
The base and the conjugate base have localized negative charge on the oxygen
atom. This results in similar stability.
Topic: Position of Equilibrium and Choice of Reagents
Section: 3.5
Difficulty Level: Easy
88. Determine if NaOH is a suitable reagent to deprotonate the following compound.
A) Yes
B) No
Ans: B
Topic: Position of Equilibrium and Choice of Reagents
Section: 3.5
Difficulty Level: Easy
A) Yes
B) No
Ans: A
Topic: Position of Equilibrium and Choice of Reagents
Section: 3.5
Difficulty Level: Medium
90. Determine if NaOH is a suitable reagent to deprotonate the following compound.
Explain why.
Ans: No.
The base has negative charge on more electronegative oxygen, whereas the
conjugate base has negative charge on less electronegative carbon atom.
Topic: Position of Equilibrium and Choice of Reagents
Section: 3.5
Difficulty Level: Medium
91. Determine if NaNH2 is a suitable reagent to deprotonate the following compound.
Explain why.
O
Ans: Yes.
The conjugate base is resonance stabilized with delocalization of charge over two
oxygen atoms. This is more stable than the amide base, which has a negative
charge localized on one nitrogen atom.
Topic: Position of Equilibrium and Choice of Reagents
Section: 3.5
Difficulty Level: Hard
Ans: No.
+
O Na
Na
OH
The base has negative charge on more electronegative oxygen atom, compared to
a nitrogen atom in the conjugate base. This results in a more stable base.
Topic: Position of Equilibrium and Choice of Reagents
Section: 3.5
Difficulty Level: Hard
93. Determine if H2O is a suitable reagent to protonate the following compound. Explain
why. Draw the complete reaction, including the curved arrow mechanism.
S Na
Ans: No.
S
S Na
H
H
+ NaOH
Sulfur is a larger atom compared to an oxygen atom and the negative charge is
spread over a larger volume of space. Furthermore the sulfur anion is resonance
stabilized. These two factors results in more stable anion and a weaker base
Topic: Leveling Effect
Section: 3.6
Difficulty Level: Easy
94.
A)
B)
C)
D)
95.
A)
B)
C)
D)
E)
Topic: Counterions
Section: 3.8
Difficulty Level: Easy
100.
A)
B)
C)
D)
What is a cation?
a negatively charged ion
a positively charged ion
a sodium atom
Both B & C
Ans: B
Topic: Counterions
Section: 3.8
Difficulty Level: Easy
101.
A)
B)
C)
D)
Topic: Counterions
Section: 3.8
Difficulty Level: Easy
102.
A)
B)
C)
D)
Topic: Counterions
Section: 3.8
Difficulty Level: Easy
103. What is a counterion in (CH3)3COK?
Ans: K+
Topic: Lewis Acids and Bases
Section: 3.9
Difficulty Level: Easy
104.
A)
B)
C)
D)
A)
B)
C)
D)
E)
Brnsted-Lowry acid
Lewis acid
Brnsted-Lowry base
Lewis base
Both C & D
Ans: E
A)
B)
C)
D)
E)
Brnsted-Lowry acid
Lewis acid
Brnsted-Lowry base
Lewis base
Both C & D
Ans: B
111.
A)
B)
C)
D)
E)
Cl
Fe
Cl
Cl
Cl
A)
B)
C)
D)
Cl
Cl
Cl
II
I
II
III
Both I & III
Ans: A
Fe
Cl
Cl
III
NH2
H
II
H
A)
B)
C)
D)
I
II
III
Both I & III
Ans: A
III
A)
B)
C)
D)
E)
I
II
III
IV
None of these
Ans: A
+ O
II
A)
B)
C)
D)
III
I
II
III
None of these
Ans: B
NH2
II
B
H
A)
B)
C)
D)
I
II
III
None of these
Ans: B
III
Section: 3.9
Difficulty Level: Easy
117. For the following reaction, identify the Lewis base.
Cl
Cl
Fe
Cl
Cl
Cl
A)
B)
C)
D)
Cl
Cl
Cl
II
I
II
III
None of these
Ans: B
Fe
Cl
Cl
III
AlCl3
Cl
Cl
Ans:
+ AlCl3
AlCl3
Cl
Cl
Lewis acid
Lewis base
H
N
NH2
Ans:
H
N
Lewis acid
NH2
Lewis base
Cl
Fe
Cl
Cl
Cl
Cl
Fe
Cl
Ans:
Cl
Cl
Cl
Cl
Cl
Fe
Cl
Cl
Cl
Cl
Fe
Cl
Cl
Cl
Cl
Lewis acid
Lewis base
H
N
NH2
Ans:
H
N
Lewis acid
NH2
Lewis base
+ BF3
Ans:
BF3
S
+ BF3
Section: 3.9
Difficulty Level: Hard
123. Predict the product(s) for the following reaction and draw the curved arrow mechanism.
O
+ AlCl3
Ans:
AlCl3
AlCl3
+ AlCl3
+ Na CN
Ans:
+ Na CN
+ HCN + Na
Base
Acid
O
H
Ans:
O
H
Base
Acid
H
N
Ans:
H
H
H
N
Base
Acid
O
H
H
N
O
+
H
N
H