Test bank for organic chemistry 10th edition by solomons

Chapter One
MULTIPLE CHOICE QUESTIONS
Topic: General
Section: 1.1
Difficulty Level: Easy
1. Credit for the first synthesis of an organic compound from an inorganic precursor is
usually given to:
A) Berzelius
B) Arrhenius
C) Kekule
D) Wohler
E) Lewis
Ans: D
Topic: Atomic Orbitals, Hybridization
Section: 1.2
Difficulty Level: Easy
2.
A)
B)
C)
D)
E)

How many sigma 1s-2sp3 bonds are there in ethane?
7
6
5
3
1
Ans: B

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Topic: Isomerism
Section: 1.3
Difficulty Level: Easy
3. Which of the following is a set of constitutional isomers?
Br
Br

I
A)
B)
C)
D)
E)

Br

II

Br

III

IV

I and II
II and III
I, II, and III

II, III, and IV
I, III, and IV
Ans: E

Topic: Isomerism
Section: 1.3
Difficulty Level: Easy
4.
A)
B)
C)
D)
E)

CH3CH2OCH2CH3 and CH3CH2CH2CH2OH are examples of what are now termed:
Structural isomers
Resonance structures
Functional isomers
Empirical isomers
Constitutional isomers
Ans: E

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Topic: Isomerism
Section: 1.3
Difficulty Level: Easy
5. Which of the following structures represent compounds that are constitutional isomers
of each other?

I

A)
B)
C)
D)
E)

II

III

IV

I and II
I and III
I, II, and III
I, II, III, and IV
II and III
Ans: C

Topic: Isomerism
Section: 1.3
Difficulty Level: Easy
6. Which compound is not a constitutional isomer of the others?
N

A)
B)

C)
D)
E)

O

N

O

O

H
N
N

O

I
II
III
I
II
III
IV
All of the above are isomers of each other.
Ans: D

IV

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Topic: Isomerism
Section: 1.3
Difficulty Level: Easy
7. Consider the following:

A)
B)
C)
D)
E)

CH3CH2CH=CHCH2CH3
I

CH3CH2CH2CH2CH=CH2
II

CH3CH=CHCH2CH2CH3
III

CH2=CHCH2CH2CH2CH3
IV

Which two structures represent the same compound?
I and II
II and III
I and III

II and IV
None of these
Ans: D

Topic: Isomerism
Section: 1.3
Difficulty Level: Easy
8. Which of the following represent a pair of constitutional isomers?
A)
and
B) CH3CH=CH2 and CH2=CHCH3
Br
Br
C)
Br

H

H

and Br

H
Br

D)

H
Br

H

Br

and

H

H

H

Br

E) More than one of these
Ans: E

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Topic: Isomerism
Section: 1.3
Difficulty Level: Easy
9. Which of the following represent pairs of constitutional isomers?
OH
O
A)
O

and

O
CH3

CH3

B)

Br

H

H

and Br

H
CH2

C)
Br

H
Br

CH3

and

H

H

CH3

D) None of these pairs
E) All of these pairs
Ans: D
Topic: Isomerism
Section: 1.3
Difficulty Level: Medium
10. Which compound is not a constitutional isomer of the others?
OH

O
O

OH

I
A)
B)
C)
D)
E)

II

III

IV

I
II
III
IV
All of the above are isomers of each other.
Ans: A

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Topic: Isomerism
Section: 1.3
Difficulty Level: Medium
11. Which compound is not a constitutional isomer of the others?
Br

Br

Br
Br

Br

A)
B)
C)
D)
E)

I
II
III
IV
I and II
II
III
IV and V
All of the above are isomers of each other.
Ans: C

V

Topic: Atomic Orbitals, Periodic Trends, Electronegativity
Section: 1.4
Difficulty Level: Easy
12.
A)
B)
C)
D)
E)

The greatest degree of ionic character is anticipated for the bond between:
H and C
H and Cl
C and Cl
H and Br
Br and Cl

Ans: B

Topic: Periodic Trends, Electronegativity
Section: 1.4
Difficulty Level: Easy
13.
A)
B)
C)
D)
E)

Select the least electronegative element from the list below:
P
N
Mg
Si
K
Ans: E

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Topic: Periodic Properties, Electronegativity
Section: 1.4A
Difficulty Level: Easy
14.
A)
B)
C)

D)
E)

Select the most electronegative element from the list below:
H
O
N
B
C
Ans: B

Topic: Lewis Structures
Section: 1.5
Difficulty Level: Medium
15. Which of the following is the Lewis structure for CH3CH2O2H?
H H
A)
H

B)
H

C

C

O

H
H

H

C

O

C

H

O

H

C

C

O

H
H

H

C

O

H
H

H

C

C

H

H

O

H

O

H

H

H

C)
H

D)
H

E)
H

H

H
C

O

H

O

H

H

O

Ans: A

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Topic: Lewis Structures
Section: 1.5
Difficulty Level: Medium
16.

A)
B)
C)
D)
E)

In which of the following does the central atom have 2 pairs of non-bonding electrons?
O3
CO2
CO3 
NH4
H2 S
Ans: E

Topic: Lewis Structures, Formal Charges
Section: 1.5
Difficulty Level: Medium
17. Which is NOT a correct Lewis structure?
..
A) H N F :
..
H
H

B)
H

C

C) H

.H.
O
..

D)
H

..
.O.

..
F:
..
..
O
H
. .. .
:O H
B

:O
.. H
E) None of these
Ans: A

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Topic: Lewis Structures, Formal Charges

Section: 1.5
Difficulty Level: Medium
18. Which of these is a correct electron-dot representation of the nitrite ion, NO2-?
..
.. .. ..
..
..
..
:O::N::O
:O:N::O
:
O
:
:
N
:
O
:
..
..
..
..
..
..
I

A)
B)
C)
D)

E)

III

II

.. .. ..
:O:N:O:
..
..

.. .. ..
:O::N:O
.. ..

IV

V

I
II
III
IV
V
Ans: A

Topic: Lewis Structures
Section: 1.5
Difficulty Level: Hard
19. Which of the following is the Lewis structure for CH3CO2H?

H H
A)
H

B)
H

C

C

H
H

H
O

C

C

O

O

O

H

O

H

H

H

C) H
C

O
H

C

H

O

C

C

O

H

O

C

O

H

D)
H

H
H

E)
H

C

H

H

Ans: D

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Topic: Lewis Structures
Section: 1.5
Difficulty Level: Hard
20. Considering Lewis structures, which of these compounds possesses a single unpaired
electron?

A) N2
B) N2O
C) NO
D) N2O4
E) O2
Ans: C
Topic: Lewis Structures
Section: 1.5
Difficulty Level: Hard
..

21.

Z
Y

A)
B)
C)
D)
E)

..

Y is a generalized structural representation which can be used for all of the

following, except:
OF2
NH2–
H2 S

BeBr2
There is no exception.
Ans: D

Topic: Lewis Structures, Formal Charges
Section: 1.6
Difficulty Level: Easy
22. Expansion of the valence shell to accommodate more than eight electrons is possible
with:
A) Fluorine
B) Nitrogen
C) Carbon
D) Sulfur
E) Beryllium
Ans: D

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Topic: Lewis Structures, Formal Charges
Section: 1.7
Difficulty Level: Easy
23. What is the formal charge on oxygen in the following structure?
H3CC

A)
B)
C)
D)
E)

O

+2
+1
0
-1
-2
Ans: B

Topic: Lewis Structures, Formal Charges
Section: 1.7
Difficulty Level: Easy
24. What is the formal charge on carbon in the following structure?
Cl

A)
B)
C)
D)
E)

C

Cl

+2
+1
0
-1

-2
Ans: C

Topic: Lewis Structures, Formal Charges
Section: 1.7
Difficulty Level: Easy
25. In which structure(s) below does the oxygen have a formal charge of +1?

..
H

O

H

H

..
O:
..

C

O

..
H

H3 C

H

H

I

..
H

II

CH3

III

s

A)
B)
C)
D)
E)

O

I only
II only
I and III
I and IV
I, III, and IV

Ans: E

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IV

CH3


Topic: Lewis Structures, Formal Charges
Section: 1.7
Difficulty Level: Easy
26. Which structure(s) contain(s) an oxygen that bears a formal charge of +1?
..
..
:O
:O
..
..
..
..
: O C O:
C
H3C
O
H
H3C
O
CH3
H C

:O
:O
..:
..: : O
..:
H
CH3
I
II
III
IV
V
A)
B)
C)
D)
E)

I and II
III and IV
V
II
I and V
Ans: B

Topic: Lewis Structures, Formal Charges
Section: 1.7
Difficulty Level: Easy
27. Which of the following molecules or ions has a nitrogen with a formal charge of -1?
(Charges on ions have been omitted.)

..
A) : N H
H

B) H
C) H

..
N

.H.
N
H

D) H3C

H

CH3

..
N
H

E) H3C C
Ans: A

CH3
N:

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Topic: Lewis Structures, Formal Charges
Section: 1.7
Difficulty Level: Easy
28. In which structure(s) below does nitrogen have a formal charge of +1?
H3C

N

CH2

H3C

..
N
..

H

..

H

N
H

..
.OH

.

..
H3C

NH2

H

I

A)
B)
C)
D)
E)

..
H3C

N
CH3

II

III

IV

I

II and IV
III and V
I and V
V
Ans: A

Topic: Lewis Structures, Formal Charges
Section: 1.7
Difficulty Level: Easy
29. Which of the following is an ion with a single negative charge?
..
A) H3C O :
.. .. . ...
B) : O N O :
..
..
C)
: O:
..
:O N
:O
..:
D) All of these
E) None of these
Ans: D

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V

CH3


Topic: Lewis Structures, Formal Charges
Section: 1.7
Difficulty Level: Easy
30. What is the formal charge on oxygen in the following structure?
..
H3 C

O

CH3

CH3

A)
B)
C)
D)
E)

+2
+1
0
-1
-2
Ans: B

Topic: Lewis Structures, Formal Charges

Section: 1.7
Difficulty Level: Easy
31. Listed below are electron dot formulas for several simple molecules and ions. All
valence electrons are shown; however, electrical charges have been omitted deliberately.

A)
B)
C)
D)
E)

H : Be : H

H
..
H:B:H
..
H

H
..
H:N:H
..

H
..
H:N:H
..
H

H
..
H:O:H
..

I

II

III

IV

V

Which of the structures actually bear(s) a positive charge?
I
II
III
III & V
IV & V
Ans: E

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Topic: Lewis Structures, Formal Charges
Section: 1.7
Difficulty Level: Easy
32. Listed below are electron dot formulas for several simple molecules and ions. All

valence electrons are shown; however, electrical charges have been omitted deliberately.

A)
B)
C)
D)
E)

H : Be : H

H
..
H:B:H
..
H

H
..
H:N:H
..

H
..
H:N:H
..
H

H
..
H:O:H

..

I

II

III

IV

V

Which of the structures is negatively charged?
I
II
III
IV
V
Ans: B

Topic: Lewis Structures, Formal Charges
Section: 1.7
Difficulty Level: Easy
33. The formal charge on sulfur in sulfuric acid is:
O
H O

S

O H

O

A)
B)
C)
D)
E)

0
-1
+1
-2
+2
Ans: A

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Topic: Lewis Structures, Formal Charges
Section: 1.7
Difficulty Level: Medium
34. In which of these cases does the central atom have a zero formal charge?
A) HFH
H
B)
H3 C O
F
C)
F

B

CH3

F

F

H

D)
H3 C

N

CH3

H
CH3

E)
H3 C

C

CH3

CH3

Ans: E
Topic: Lewis Structures, Formal Charges
Section: 1.7
Difficulty Level: Medium
35. Which compound contains a nitrogen atom with a formal positive charge?

A)
B)
C)
D)
E)

N

H
N

N

I

II

III

I
II
III
More than one of the above
None of the above

Ans: D

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Topic: Atomic Orbitals, Lewis Structures, Resonance
Section: 1.8
Difficulty Level: Easy
36. Which of the following pairs are NOT resonance structures?
A)
:

and

:

O

:

:

N

:

:

O

O

N

O

..

:
H3 C

O

C

O

H3 C

N

H 3C

..
..

and

:

O

..

C

:

:

..

O

:

:
:

B)

:

..
..

:

:

H 3C

:

C)

O

N

O

O

:

and

:

..
:
..

O

D) Each of these pairs represents resonance structures.
E) None of these pairs represents resonance structures.
Ans: C
Topic: Resonance

Section: 1.8
Difficulty Level: Medium
37. Which of the following species is/are not a resonance form(s) of the anionic species in
the box?
S

S

S

I

A)
B)
C)
D)
E)

S

II

I
II and III
III and IV
I and IV
I and III
Ans: D

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III

HS

IV


Topic: Resonance
Section: 1.8
Difficulty Level: Medium
38. Which of the following species is a resonance form of the species in the box?
P(CH3)2

N
H

P(CH3)2

N
H

P(CH3)2

N
H

N
H

I

A)
B)
C)
D)
E)

P(CH3)2

II

P(CH3)2

N
H

III

IV

I
II
III
IV
None of the above are correct resonance forms.
Ans: C

Topic: Resonance
Section: 1.8

Difficulty Level: Medium
39. Which of the following species is/are a resonance form(s) of the species in the box?

N

N

N

I

A)
B)
C)
D)
E)

N

II

I and II
I and III
III and IV
III
More than two of them are correct resonance forms.
Ans: B

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N

III

IV


Topic: Resonance
Section: 1.8
Difficulty Level: Medium
40. Which of the following species is not a resonance form of the following species?
O

A) O

B)
O

C)
D)

O

O

E)
O

Ans: A
Topic: Resonance

Section: 1.8
Difficulty Level: Medium
41. Which of the following species is/are a resonance form(s) of the species in the box?
O

O

O

O

H3CO

H3CO

H3CO

H3CO

I

A)
B)
C)
D)
E)

II

I and II

II and III
III
II
More than two of them are correct resonance forms.
Ans: D

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O
C

III

H3CO

IV


Topic: Resonance
Section: 1.8
Difficulty Level: Medium
42. Which of the following species is/are not a resonance form(s) of the species in the box?

I

A)
B)
C)
D)
E)

II

IV

III

I
II
III
IV
More than two of them are incorrect resonance forms.
Ans: B

Topic: Resonance
Section: 1.8
Difficulty Level: Medium
43. Which of the following species is/are not a resonance form(s) of the species in the box?
SCH3

SCH3

SCH3

I

A)
B)
C)
D)

E)

II

I
II
III
IV
More than two of them are incorrect resonance forms.
Ans: A

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SCH3

SCH3

III

IV


Topic: Resonance
Section: 1.8
Difficulty Level: Medium
44. Which of the following species is/are not a resonance form(s) of the species in the box?

N

N

N

N

I

A)
B)
C)
D)
E)

N

II

IV

III

I and II
II and III
III and IV
I and IV
II and IV
Ans: C

Topic: Resonance
Section: 1.8

Difficulty Level: Medium
45. Which of the following species contributes more to the overall hybrid for the species in
the box?

N

N

N

I

A)
B)
C)
D)
E)

N

II

I
II
III
IV
The one in the box.
Ans: C

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N

III

IV


Topic: Resonance
Section: 1.8
Difficulty Level: Medium
46. Which of the following species contributes more to the overall hybrid for the species in
the box?

N

N

N

I

A)
B)
C)
D)
E)

N

II

N

IV

III

I
II
III
IV
The one in the box.
Ans: A

Topic: Resonance
Section: 1.8
Difficulty Level: Medium
47. Which of the following species contributes more to the overall hybrid for the species in
the box?
S

S

S

I

A)
B)

C)
D)
E)

S

II

I
II
III
IV
The one in the box.
Ans: B

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III

HS

IV


Topic: Resonance
Section: 1.8
Difficulty Level: Hard
48. Which of the following species is a resonance form of the following species?
N

A)
N

B)
N

C)
N

D)
N

E) All the above are correct resonance forms.
Ans: D

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Topic: Resonance
Section: 1.8
Difficulty Level: Hard
49. Which of the following structures is/are not a resonance form of the following species?

N

A)

N

B)

N
H

C)

C

N

D)

N

E) None of the above are correct resonance forms.
Ans: E

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Topic: Resonance
Section: 1.8
Difficulty Level: Hard
50. Which of the following species are resonance forms of the species in the box?
O

O

CN

CN

I
A)
B)
C)
D)
E)

O

O

CN

O

CN

II

C
N

III

IV

I and III
I and II

III and IV
II and IV
All of the above are correct resonance forms.
Ans: C

Topic: Resonance
Section: 1.8
Difficulty Level: Hard
51. Which of the following species contributes more to the overall hybrid for the species in
the box?
P(CH3)2

N
H

P(CH3)2

N
H

P(CH3)2

N
H

I

A)
B)
C)

D)
E)

P(CH3)2

N
H

II

I
II
III
IV
The one in the box.
Ans: C

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P(CH3)2

N
H

III

IV