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Chapter Three

Topic: Introduction to Brnsted-Lowry Acids and Bases


Section: 3.1
Difficulty Level: Easy
1. A Brnsted-Lowry acid is defined as a ____ and a Brnsted-Lowry base is defined as a
____.
A) proton acceptor, proton donor
B) proton donor, proton donor
C) proton acceptor, proton acceptor
D) proton donor, proton acceptor
E) None of these
Ans: D
Topic: Introduction to Brnsted-Lowry Acids and Bases
Section: 3.1
Difficulty Level: Easy
2. Provide a definition of a Brnsted-Lowry acid.
Ans: A Brnsted-Lowry acid is a proton donor.
Topic: Introduction to Brnsted-Lowry Acids and Bases
Section: 3.1
Difficulty Level: Easy
3. Provide a definition of a Brnsted-Lowry base.
Ans: A Bronsted-Lowry base is a proton acceptor.
Topic: Introduction to Brnsted-Lowry Acids and Bases
Section: 3.1
Difficulty Level: Easy
4. For the following reaction, which reactant functions as an acid?
O

A) I
B) II
C) neither
Ans: B

OH

II

Topic: Introduction to Brnsted-Lowry Acids and Bases


Section: 3.1

Difficulty Level: Easy


5. For the following reaction, which reactant functions as a base?
O

A) I
B) II
C) neither
Ans: A

OH

II

Topic: Introduction to Brnsted-Lowry Acids and Bases


Section: 3.1
Difficulty Level: Easy
6. For the following reaction, which reactant functions as an acid?
H2SO4

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

8. For the following reaction, which reactant functions as a base?


H

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)

Which of the following is not a Bronsted-Lowry acid?


CH3OH
CH3CH3
CH3NH2
CH3SH
None of these
Ans: B

Topic: Introduction to Brnsted-Lowry Acids and Bases


Section: 3.1
Difficulty Level: Medium
10.
A)
B)
C)
D)
E)

Which of the following is not a Bronsted-Lowry base?


CH3OH
CH3OCH3
CH3NH2
CH3CH3
None of these
Ans: D

Topic: Introduction to Brnsted-Lowry Acids and Bases


Section: 3.1
Difficulty Level: Easy
11.
A)
B)
C)
D)
E)

In a Bronsted-Lowry acid-base reaction the product(s) is (are) a _______.


Lewis acid
conjugate acid only
Lewis acid-base pair
conjugate acid-conjugate base pair
None of these
Ans: D

Topic: Introduction to Brnsted-Lowry Acids and Bases

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)

A loss of proton from a Brnsted-Lowry acid results in a ___.


Lewis acid
conjugate acid
conjugate base
conjugate acid-base pair
None of these
Ans: C

Topic: Introduction to Brnsted-Lowry Acids and Bases


Section: 3.1
Difficulty Level: Easy
14.
A)
B)
C)
D)
E)

A gain of proton by a Brnsted-Lowry base results in a ___.


Lewis acid
conjugate acid
conjugate base
conjugate acid-base pair
None of these
Ans: B

Topic: Introduction to Brnsted-Lowry Acids and Bases


Section: 3.1
Difficulty Level: Easy
15.
A)
B)
C)
D)
E)

What is the conjugate base of nitric acid?


NO3NO2HNO3
HNO2
None of these
Ans: A

Topic: Introduction to Brnsted-Lowry Acids and Bases


Section: 3.1
Difficulty Level: Easy

16.
A)
B)
C)
D)
E)

What is the conjugate base of phosphoric acid?


HPO42H2PO4HPO32PO43None of these
Ans: B

Topic: Introduction to Brnsted-Lowry Acids and Bases


Section: 3.1
Difficulty Level: Easy
17.
A)
B)
C)
D)
E)

What is the conjugate base of CH3CH2SH?


CH3CH2SCH3CH2CH3CH2SH2+
CH3CH2S2None of these
Ans: A

Topic: Introduction to Brnsted-Lowry Acids and Bases


Section: 3.1
Difficulty Level: Easy
18. Draw the conjugate acid of CH3CH2OH.
Ans:
CH3CH2OH2

Topic: Introduction to Brnsted-Lowry Acids and Bases


Section: 3.1
Difficulty Level: Easy
19. Draw the conjugate acid of CH3OCH3
Ans:
CH3OCH3
H

Topic: Introduction to Brnsted-Lowry Acids and Bases


Section: 3.1
Difficulty Level: Medium

20. Draw the conjugate acid of the following compound.


O

Ans:

OH

Topic: Introduction to Brnsted-Lowry Acids and Bases


Section: 3.1
Difficulty Level: Easy
21. Draw the conjugate base of CH3CCH.
Ans:
H3C

Topic: Introduction to Brnsted-Lowry Acids and Bases


Section: 3.1
Difficulty Level: Easy
22. Draw the conjugate base of CH3CH2NH2.
Ans:
CH3CH2NH
Topic: Introduction to Brnsted-Lowry Acids and Bases
Section: 3.1
Difficulty Level: Medium
23. Draw the conjugate base of the following compound.
OH

Ans:

Topic: Introduction to Brnsted-Lowry Acids and Bases


Section: 3.1
Difficulty Level: Medium

24. Draw the conjugate base of the following compound.


OH
H
O
O

Ans:

H
O

Topic: Flow of Electron Density: Curved Arrow Notation


Section: 3.2
Difficulty Level: Easy
25. Which is the conjugate acid in the following reaction?
CH3CH2SH + Na OH
A)
B)
C)
D)
E)

I
I
II
III
IV
Both I & IV
Ans: D

II

CH3CH2S Na + H2O
IV
III

Topic: Flow of Electron Density: Curved Arrow Notation


Section: 3.2
Difficulty Level: Easy
26. Which is the conjugate base in the following reaction?
CH3CH2SH + Na OH
I
A)
B)
C)
D)
E)

I
II
III
IV
Both II & III
Ans: C

II

CH3CH2S Na + H2O
IV
III

Topic: Flow of Electron Density: Curved Arrow Notation


Section: 3.2
Difficulty Level: Easy

27. Which is the conjugate acid in the following reaction?


+ CH3CH2 Li

A)
B)
C)
D)
E)

N
H

IV

III

II

+ CH3CH3 + Li

I
II
III
IV
Both I & IV
Ans: D

Topic: Flow of Electron Density: Curved Arrow Notation


Section: 3.2
Difficulty Level: Easy
28. Which is the conjugate base in the following reaction?
+ CH3CH2 Li

A)
B)
C)
D)
E)

N
H

III

II

+ CH3CH3 + Li
IV

I
II
III
IV
Both I & III
Ans: C

Topic: Flow of Electron Density: Curved Arrow Notation


Section: 3.2
Difficulty Level: Medium
29. For the following reaction label the acid, base, conjugate acid and conjugate base.
CH3CH2SH + Na OH
Ans:
CH3CH2SH + Na OH
acid

base

CH3CH2S Na + H2O
CH3CH2S Na + H2O
conjugate base

Topic: Flow of Electron Density: Curved Arrow Notation


Section: 3.2
Difficulty Level: Medium

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

Topic: Flow of Electron Density: Curved Arrow Notation


Section: 3.2
Difficulty Level: Medium
31. For the following reaction label the acid, base, conjugate acid and conjugate base.
+ NaOH

Na

+ H2O

Ans:
+ NaOH

acid

base

Na

conjugate base

+ H2O

conjugate acid

Topic: Flow of Electron Density: Curved Arrow Notation


Section: 3.2
Difficulty Level: Easy
32. The tail of the curved arrow must start at ____ electron density and the head must end at
____ electron density.
A) low, high
B) high, high
C) low, low
D) high, low
Ans: D
Topic: Flow of Electron Density: Curved Arrow Notation
Section: 3.2
Difficulty Level: Easy
33. Provide a curved arrow mechanism for the following acid-base reaction.
H

+ Na OH

S Na

+ H2O

Ans:
H
S

+ Na OH

Topic: Flow of Electron Density: Curved Arrow Notation

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

Topic: Flow of Electron Density: Curved Arrow Notation


Section: 3.2
Difficulty Level: Medium
35. Provide a curved arrow mechanism for the following acid-base reaction.
H
N

H +

NH2

H +

NH3

Ans:

H
N

H +

NH2

H +

NH3

Topic: Flow of Electron Density: Curved Arrow Notation


Section: 3.2
Difficulty Level: Medium
36. Identify the acid and the base and provide a curved arrow mechanism for the following
reaction.

Ans:
O
H

acid

+ Na OH
base

Topic: Flow of Electron Density: Curved Arrow Notation


Section: 3.2
Difficulty Level: Medium

+ 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

Topic: Flow of Electron Density: Curved Arrow Notation


Section: 3.2
Difficulty Level: Medium
38. Identify the acid and the base and provide a curved arrow mechanism for the following
reaction.
Na

+ H2O

+ NaOH

Ans:

Topic: Flow of Electron Density: Curved Arrow Notation


Section: 3.2
Difficulty Level: Easy
39. The following reaction mechanism contains error. Which of the following statements
correctly describes the curved arrows consistent with the reaction?
O

O
H

+ Na H

O Na

+ H2

A) The curved arrow should start at the carbonyl oxygen atom


B) The curved arrow should start at the hydride, go to the hydrogen connected to oxygen
and a second arrow should start from the OH covalent bond and go to the oxygen
C) The curved arrow should start at the oxygen atom of the OH
D) There should be one more arrow
Ans: B
Topic: Flow of Electron Density: Curved Arrow Notation
Section: 3.2
Difficulty Level: Medium

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

Topic: Flow of Electron Density: Curved Arrow Notation


Section: 3.2
Difficulty Level: Medium
41. For the following reaction mechanism, identify the error, if any and describe the
modification necessary by drawing the correct mechanism.
O

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

Topic: Flow of Electron Density: Curved Arrow Notation


Section: 3.2
Difficulty Level: Hard

+ NaBr
OH

42. Predict the products for the following acid-base reaction.


O
H

Ans:

+ Na OH

Na
O

+ H2O

Topic: Flow of Electron Density: Curved Arrow Notation


Section: 3.2
Difficulty Level: Hard
43. Predict the products for the following acid-base reaction.

Ans:

Na

+ NH3

Topic: Brnsted-Lowry Acid: Quantitative Perspective


Section: 3.3
Difficulty Level: Easy

44. What is the Keq for the following reaction?


+ H3O

+ 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

Topic: Brnsted-Lowry Acid: Quantitative Perspective


Section: 3.3
Difficulty Level: Easy
45. Which of the following compounds is most acidic?
O

OH

A)
B)
C)
D)
E)

II

III

I
II
III
IV
None of these
Ans: B

Topic: Brnsted-Lowry Acid: Quantitative Perspective


Section: 3.3
Difficulty Level: Easy

NH2

IV

46. Which of the following compounds is most basic?


O

OH

A)
B)
C)
D)
E)

NH2

II

IV

III

I
II
III
IV
None of these
Ans: D

Topic: Brnsted-Lowry Acid: Quantitative Perspective


Section: 3.3
Difficulty Level: Medium
47. Which of the following compounds is most acidic?
OH

OH

NH2
NH2

A)
B)
C)
D)
E)

II

III

I
II
III
IV
All of these
Ans: A

Topic: Brnsted-Lowry Acid: Quantitative Perspective


Section: 3.3
Difficulty Level: Medium

IV

48. Which of the following compounds is most basic?


OH

OH

NH2
NH2

A)
B)
C)
D)
E)

II

III

IV

I
II
III
IV
All of these
Ans: C

Topic: Brnsted-Lowry Acid: Quantitative Perspective


Section: 3.3
Difficulty Level: Medium
49. Which of the following compounds is most basic?
O

A)
B)
C)
D)
E)

II

III

I
II
III
IV
All of these
Ans: D

Topic: Brnsted-Lowry Acid: Quantitative Perspective


Section: 3.3
Difficulty Level: Hard

IV

50. Tryptophan, an essential amino acid, is important in the synthesis of the


neurotransmitter serotonin in the body. It has the following structure. Circle the three
most acidic protons in tryptophan.
O
O
H
H

N
H
N
H

Ans:

O
H
H

N
H
N
H

Topic: Brnsted-Lowry Acid: Quantitative Perspective


Section: 3.3
Difficulty Level: Hard
51. Histidine an amino acid has the following structure. Circle the three most acidic protons
in histidine.
H

CH2

H
H

CH2

C
C

Ans:
H

C
C
N

H
H

Topic: Brnsted-Lowry Acid: Quantitative Perspective


Section: 3.3
Difficulty Level: Medium

52. For the following acid-base reaction, predict which side the equilibrium is favored.
+ NaOH

+ H2O

A) favor right side


B) favor left side
C) neither
Ans: A
Topic: Brnsted-Lowry Acid: Quantitative Perspective
Section: 3.3
Difficulty Level: Medium
53. For the following acid-base reaction, predict which side the equilibrium is favored.
OH

+ H2O

+ H3O

A) favor right side


B) favor left side
C) neither
Ans: B
Topic: Brnsted-Lowry Acid: Quantitative Perspective
Section: 3.3
Difficulty Level: Hard
54. For the following acid-base reaction, predict which side the equilibrium is favored.
O

H
N

O
H

A) favor right side


B) favor left side
C) neither
Ans: A
Topic: Brnsted-Lowry Acid: Quantitative Perspective
Section: 3.3
Difficulty Level: Hard

O
N
H

55. For the following acid-base reaction, predict which side the equilibrium is favored.
O

Li

A) favor right side


B) favor left side
C) neither
Ans: A

+
Li

Topic: Brnsted-Lowry Acid: Qualitative Perspective


Section: 3.4
Difficulty Level: Easy
56.
A)
B)
C)
D)

Which of the following compounds is most acidic?


HF
HCl
HBr
HI
Ans: D

Topic: Brnsted-Lowry Acid: Qualitative Perspective


Section: 3.4
Difficulty Level: Easy
57.
A)
B)
C)
D)

Which of the following compounds is most acidic?


CH3OH
HCl
CH3SH
CH3NH2
Ans: B

Topic: Brnsted-Lowry Acid: Qualitative Perspective


Section: 3.4
Difficulty Level: Medium
58. Which of the following compounds is more acidic? Explain why.
HF and HBr
Ans: HBr is more acidic than HF. The Br- ion has larger atomic size than the F- ion,
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: Medium

59. Which of the following compounds is more acidic? Explain why.


CH3OH and CH3NH2
Ans: CH3OH is more acidic than CH3NH2. The conjugate base CH3O- is more stable
than CH3NH-, because oxygen is more electronegative than nitrogen and can
stabilize the negative charge better, resulting in weak conjugate base.
Topic: Brnsted-Lowry Acid: Qualitative Perspective
Section: 3.4
Difficulty Level: Medium
60. Determine which proton is most acidic in the following compound. Explain why.
H

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

Topic: Brnsted-Lowry Acid: Qualitative Perspective


Section: 3.4
Difficulty Level: Easy

62. Which of the following compounds is most acidic?


O

OH

OH

A)
B)
C)
D)

II

I
II
III
IV
Ans: A

IV

III

Topic: Brnsted-Lowry Acid: Qualitative Perspective


Section: 3.4
Difficulty Level: Medium
63. Which of the indicated protons is most acidic?
H

A)
B)
C)
D)

I
II
III
IV
Ans: D

II

III

IV

Topic: Brnsted-Lowry Acid: Qualitative Perspective


Section: 3.4
Difficulty Level: Medium
64. Rank the indicated protons in decreasing order (most to least) of acidity.
IH

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

Topic: Brnsted-Lowry Acid: Qualitative Perspective


Section: 3.4
Difficulty Level: Medium
65. Which compound has the most acidic proton? Explain your choice.
O

II

Ans: Compound II.


The conjugate base of both compounds is resonance stabilized. For compound II
the negative charge ends up on more electronegative oxygen atom in one of the
resonance structure whereas in compound I the negative charge is on less
electronegative carbon atom in every resonance structure.
Topic: Brnsted-Lowry Acid: Qualitative Perspective
Section: 3.4
Difficulty Level: Hard
66. Which of the indicated protons is most acidic? Explain your choice.
IH

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

Topic: Brnsted-Lowry Acid: Qualitative Perspective


Section: 3.4
Difficulty Level: Easy
68. Which of the following compounds is most acidic?
O

F
OH
F

A)
B)
C)
D)

OH

OH

Cl

II

I
II
III
IV
Ans: A

OH

III

Br

IV

Topic: Brnsted-Lowry Acid: Qualitative Perspective


Section: 3.4
Difficulty Level: Easy
69. Which of the following compounds is most acidic?
O

OH

OH
F

A)
B)
C)
D)

Cl

OH

II

OH
Br

III

IV

I
II
III
IV
Ans: B

Topic: Brnsted-Lowry Acid: Qualitative Perspective


Section: 3.4
Difficulty Level: Medium
70. Which of the following compounds is most acidic?
O

OH

A)
B)
C)
D)

Cl

I
II
III
IV
Ans: D

OH

OH

II
Cl

III

Cl

OH
F

IV

Topic: Brnsted-Lowry Acid: Qualitative Perspective


Section: 3.4
Difficulty Level: Hard
71. Rank the following compounds in decreasing order (most to least) of acidity.
O

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

Topic: Brnsted-Lowry Acid: Qualitative Perspective


Section: 3.4
Difficulty Level: Medium
72. Which of the indicated protons is most acidic?
II H

I H

S
O
H
O

A)
B)
C)
D)
E)

IV

O
H

III

I
II
III
IV
All of these
Ans: D

Topic: Brnsted-Lowry Acid: Qualitative Perspective


Section: 3.4
Difficulty Level: Medium

Br

OH
Br

IV

73. Which of the indicated protons is most acidic? Explain why.


H

CF3

II H
N
H

Ans: H-II is more acidic.


The conjugate base is stabilized by the inductive effect of the adjacent fluorine
atoms, which are closer to position II than position I.
Topic: Brnsted-Lowry Acid: Qualitative Perspective
Section: 3.4
Difficulty Level: Medium
74. Explain why phenol is more acidic than ethanol.
O
H
H
O

ethanol

Phenol

Ans: The conjugate base of phenol is resonance stabilized, resulting in a weaker


conjugate base. The conjugate base of ethanol has localized charge.
Topic: Brnsted-Lowry Acid: Qualitative Perspective
Section: 3.4
Difficulty Level: Medium
75. Which of the following compounds is more acidic? Explain why.
O
H

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

A) favor right side


B) favor left side
C) neither
Ans: A
Topic: Position of Equilibrium and Choice of Reagents
Section: 3.5
Difficulty Level: Easy
78. For the following acid-base reaction, predict which side the equilibrium is favored.
C

A) favor right side


B) favor left side
C) neither
Ans: B
Topic: Position of Equilibrium and Choice of Reagents
Section: 3.5
Difficulty Level: Easy

79. For the following acid-base reaction, predict which side the equilibrium is favored.
+

A) favor right side


B) favor left side
C) neither
Ans: A
Topic: Position of Equilibrium and Choice of Reagents
Section: 3.5
Difficulty Level: Easy
80. For the following acid-base reaction, predict which side the equilibrium is favored.
OH

SH

A) favor right side


B) favor left side
C) neither
Ans: B
Topic: Position of Equilibrium and Choice of Reagents
Section: 3.5
Difficulty Level: Medium
81. For the following acid-base reaction, predict which side the equilibrium is favored.
Explain why.
OH

SH

Ans: Favors the left side.


Sulfur is a larger atom and the negative charge is spread over a larger volume of
space. This results in more stable anion and a weaker base.
Topic: Position of Equilibrium and Choice of Reagents
Section: 3.5
Difficulty Level: Medium

82. For the following acid-base reaction, predict which side the equilibrium is favored.
Explain why.
+

Ans: Favors the right side.


Both the base and the conjugate base have negative charge on carbon atom. The
negative charge on conjugate base is stabilized via resonance, resulting in a more
stable base.
Topic: Position of Equilibrium and Choice of Reagents
Section: 3.5
Difficulty Level: Medium
83. For the following acid-base reaction, predict which side the equilibrium is favored.
Explain why.
O

F3C

OH

OH

+
F3C

Ans: Favors the right side.


Both the base and the conjugate base have negative charge on oxygen atom. The
negative charge on conjugate base is stabilized via inductive effect of the fluorine
on the adjacent carbon, resulting in a more stable base.
Topic: Position of Equilibrium and Choice of Reagents
Section: 3.5
Difficulty Level: Easy
84. Determine if H2O is a suitable reagent to protonate the following compound.
O

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

Topic: Position of Equilibrium and Choice of Reagents


Section: 3.5
Difficulty Level: Medium
86. Determine if H2O is a suitable reagent to protonate the following compound. Explain
why.
N
H

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

89. Determine if NaNH2 is a suitable reagent to deprotonate the following compound.


O

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

92. Determine if CH3CH2ONa is a suitable reagent to deprotonate the following compound.


Explain why. Draw the complete reaction, including the curved arrow mechanism.
N
H

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)

Which of the following solvents can be used with NaNH2?


CH3CH2OH
CH3OH
H2O
Liquid NH3
Ans: D

Topic: Leveling Effect


Section: 3.6
Difficulty Level: Easy

95.
A)
B)
C)
D)
E)

Which of the following solvents can not be used with (CH3)3COK?


(CH3CH2)2O
(CH3)3COH
H2O
Liquid NH3
None of these
Ans: C

Topic: Leveling Effect


Section: 3.6
Difficulty Level: Easy
96.
A)
B)
C)
D)
E)

Which of the following solvents can be used with (CH3)3CLi?


CH3CH2OH
CH3OH
H2O
Liquid NH3
CH3(CH2)4CH3
Ans: E

Topic: Leveling Effect


Section: 3.6
Difficulty Level: Easy
97. As a result of the "leveling effect," the strongest acid that can exist in appreciable
concentration in aqueous solution is ____.
A) H2SO4
B) HCl
C) H3O+
D) HNO3
E) All of these
Ans: C
Topic: Leveling Effect
Section: 3.6
Difficulty Level: Medium
98. What is the leveling effect?
Ans: It is the deprotonation of a solvent by a base or protonation of solvent by an acid.
Topic: Leveling Effect
Section: 3.6
Difficulty Level: Medium
99. What is the strongest base that can be used with water as a solvent?
Ans: hydroxide

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)

What is the counterion in NaOCH2CH3?


Na+
NaO
CH3CH2
CH3CH2O
Ans: A

Topic: Counterions
Section: 3.8
Difficulty Level: Easy
102.
A)
B)
C)
D)

What is the counterion in (CH3)3CLi?


CH3+
CH3
C(CH3)3
Li+
Ans: 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 Lewis acid is defined as _____.


a proton donor
an electron pair donor
a hydroxide donor
an electron pair acceptor
Ans: D

Topic: Lewis Acids and Bases


Section: 3.9
Difficulty Level: Easy
105.
A)
B)
C)
D)

A Lewis base is defined as _____.


a proton donor
an electron pair donor
a hydroxide donor
an electron pair acceptor
Ans: B

Topic: Lewis Acids and Bases


Section: 3.9
Difficulty Level: Easy
106.
A)
B)
C)
D)
E)

CH3CH2OCH2CH3, is best classified as a ____.


Brnsted-Lowry acid
Lewis acid
Brnsted-Lowry base
Lewis base
Both C & D
Ans: E

Topic: Lewis Acids and Bases


Section: 3.9
Difficulty Level: Easy
107.
A)
B)
C)
D)
E)

BF3, is best classified as a ____.


Brnsted-Lowry acid
Lewis acid
Brnsted-Lowry base
Lewis base
Both A & D
Ans: B

Topic: Lewis Acids and Bases


Section: 3.9
Difficulty Level: Easy

108. The following compound is best classified as a ____.


S

A)
B)
C)
D)
E)

Brnsted-Lowry acid
Lewis acid
Brnsted-Lowry base
Lewis base
Both C & D
Ans: E

Topic: Lewis Acids and Bases


Section: 3.9
Difficulty Level: Easy
109. The following compound is best classified as a ____.

A)
B)
C)
D)
E)

Brnsted-Lowry acid
Lewis acid
Brnsted-Lowry base
Lewis base
Both C & D
Ans: B

Topic: Lewis Acids and Bases


Section: 3.9
Difficulty Level: Medium
110.
A)
B)
C)
D)
E)

Which of the following compounds is not a Lewis acid?


BH3
AlCl3
CH3CH3
CH3CH2+
Both C & D
Ans: C

Topic: Lewis Acids and Bases


Section: 3.9
Difficulty Level: Medium

111.
A)
B)
C)
D)
E)

Which of the following compounds is not a Lewis acid?


BF3
FeCl3
CH3CH2+
Ph3P
none of these
Ans: D

Topic: Lewis Acids and Bases


Section: 3.9
Difficulty Level: Easy
112. For the following reaction, identify the Lewis acid.
Cl

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

Topic: Lewis Acids and Bases


Section: 3.9
Difficulty Level: Easy
113. For the following reaction, identify the Lewis acid.
H
H
H

NH2
H

II
H

A)
B)
C)
D)

I
II
III
Both I & III
Ans: A

Topic: Lewis Acids and Bases


Section: 3.9
Difficulty Level: Medium

III

114. For the following reaction, identify the Lewis acid.

A)
B)
C)
D)
E)

I
II
III
IV
None of these
Ans: A

Topic: Lewis Acids and Bases


Section: 3.9
Difficulty Level: Medium
115. For the following reaction, identify the Lewis acid.
O
N

+ O

II

A)
B)
C)
D)

III

I
II
III
None of these
Ans: B

Topic: Lewis Acids and Bases


Section: 3.9
Difficulty Level: Easy
116. For the following reaction, identify the Lewis base.
H
H
H

NH2

II

B
H

A)
B)
C)
D)

I
II
III
None of these
Ans: B

Topic: Lewis Acids and Bases

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

Topic: Lewis Acids and Bases


Section: 3.9
Difficulty Level: Medium
118. For the following reaction, identify the Lewis acid and the Lewis base.
+ AlCl3

AlCl3

Cl

Cl

Ans:
+ AlCl3

AlCl3

Cl

Cl

Lewis acid

Lewis base

Topic: Lewis Acids and Bases


Section: 3.9
Difficulty Level: Medium
119. For the following reaction, identify the Lewis acid and the Lewis base.
H

H
N

NH2

Ans:

H
N

Lewis acid

NH2

Lewis base

Topic: Lewis Acids and Bases


Section: 3.9
Difficulty Level: Hard
120. For the following reaction, identify the Lewis acid and the Lewis base and draw the
curved arrow mechanism.
Cl

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

Topic: Lewis Acids and Bases


Section: 3.9
Difficulty Level: Hard
121. For the following reaction, identify the Lewis acid and the Lewis base and draw the
curved arrow mechanism.
H

H
N

NH2

Ans:

H
N

Lewis acid

NH2

Lewis base

Topic: Lewis Acids and Bases


Section: 3.9
Difficulty Level: Hard
122. Predict the product(s) for the following reaction and draw the curved arrow mechanism.
S

+ BF3

Ans:

BF3
S

+ BF3

Topic: Lewis Acids and Bases

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

Topic: Integrated Problems


Section: 3.1-3.5
Difficulty Level: Hard
124. For the following reaction identify the acid and the base and predict the products. Draw
the curved arrow mechanism for the formation of products and predict the direction of
the equilibrium.
H
N

+ Na CN

Ans:

+ Na CN

+ HCN + Na

Base

Acid

Topic: Integrated Problems


Section: 3.1-3.5
Difficulty Level: Hard
125. For the following reaction identify the acid and the base and predict the products. Draw
the curved arrow mechanism for the formation of products and predict the direction of
the equilibrium.
O

O
H

Ans:

O
H

Base

Acid

Topic: Integrated Problems


Section: 3.1-3.5
Difficulty Level: Hard
126. For the following reaction identify the acid and the base and predict the products. Draw
the curved arrow mechanism for the formation of products and predict the direction of
the equilibrium.
O

H
N

Ans:

H
H

H
N

Base

Acid

O
H
H

N
O

+
H

N
H