Organic Chemistry 1st Edition Test Bank by David R. Klein

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Chapter 2
Topic: Molecular Representations
Section: 2.1
Difficulty Level: Easy
1. What is the molecular formula for the following structure?
O
A. C2H6O
B. C4H6O
C. C4H10O
D. C2H4O
Ans: C
Topic: Molecular Representations
Section: 2.1
Difficulty Level: Easy
2. Which of the following structures is of a compound with a molecular formula of
C2H6O?
O OH

CH3CH2OCH2CH3 CH3CH2OCH3

1 2 3

4

A. 1
B. 2
C. 3
D. 4
Ans: B
Topic: Molecular Representations
Section: 2.1
Difficulty Level: Easy
3. Which of the following is the correct condensed structure for the following structure?
OH

CH3CH2OCH2CH3 CH3CH2O

1 2 3

4

CH3CHCH2OH (CH3

)2CHCH2OH

A. 1
B. 2
C. 3
D. 4

Ans: B
Topic: Molecular Representations
Section: 2.1
Difficulty Level: Easy
4. Which of the following is the correct Lewis structure for the following structure?
O

1 2 3 4
H C
H
H
C
O
H C
H
H
C
O

H C
H
H
C
O

H C
H
H
C
O

H O

H
H

A. 1
B. 2
C. 3
D. 4
Ans: B
Topic: Molecular Representations
Section: 2.1
Difficulty Level: Easy
5. Which of the following is the correct bond-line structure for (CH3)4C?

1 2 3

4

A. 1
B. 2
C. 3
D. 4
Ans: C
Topic: Molecular Representations
Section: 2.1
Difficulty Level: Medium
6. Draw the bond-line structure for (CH3)4C?
Ans:
Topic: Molecular Representations

Section: 2.1
Difficulty Level: Easy
7. Which of the following is the correct molecular formula for (CH3)4C?
C4H12 C3H9

1 2 3

4

C2H12 C5H12
A. 1
B. 2
C. 3
D. 4
Ans: B
Topic: Molecular Representations
Section: 2.1
Difficulty Level: Easy
8. Which of the following is the correct Lewis structure for CH3CH2CH2NH2?

1 2 3 4

H C
H
H
C C
H
H
H
H
N
H
H

H C
H
H
C C
H
H
H
H
N
H
H

H C C
H
H
H
H
N
H
H

NH2

A. 1
B. 2
C. 3
D. 4
Ans: B
Topic: Molecular Representations
Section: 2.1
Difficulty Level: Easy
9. Which of the following is a valid Lewis structure for a compound with the molecular
formula of C4H11N?

1 2 3 4

H C
H
H
C C
H
C
H
H

H C
H
H
C C
H
H
H
H
C C C C
H
H
H
H
N
H
H
H
H
C

C
C C
C
H N
H
H
H
H
H H
H
H

H
N

H
H
H N

A. 1
B. 2
C. 3
D. 4
Ans: A
Topic: Molecular Representations

Section: 2.1
Difficulty Level: Medium
10. Draw a valid Lewis structure for the following compound.

Ans:
C
C
C C
H H
C
C C C
C
C

Topic: Molecular Representations
Section: 2.1
Difficulty Level: Hard
11. Draw a valid Lewis structure for the following compound.
H3CCOH

Ans:
O
C H C H
H H
Topic: Molecular Representations
Section: 2.1
Difficulty Level: Hard
12. Draw a valid Lewis structure for the following compound.
H3CSOCH3

Ans:
O
S
C C
H
H H H
H
H

Topic: Bond-Line Structures
Section: 2.2
Difficulty Level: Easy
13. Which of the following bond-line structures are of the same compound?

1 2 3

4

A. 1 and 2
B. 2 and 3
C. 3 and 4
D. 1 and 3

Ans: D
Topic: Bond-Line Structures
Section: 2.2
Difficulty Level: Easy
14. Which of the following bond-line structures are of the same compound?

1 2 3

4

A. 1 and 2
B. 2 and 3
C. 3 and 4
D. 2 and 4
Ans: D
Topic: Bond-Line Structures
Section: 2.2
Difficulty Level: Easy
15. In the following reaction, how many H’s do you add or lose?
A. Add 1
B. Add 2
C. Lose 1
D. Lose 2
E. No change
Ans: D
Topic: Bond-Line Structures
Section: 2.2
Difficulty Level: Easy
16. In the following reaction, how many H’s do you add or lose?
O OH

A. Add 1
B. Add 2
C. Lose 1
D. Lose 2
E. No change
Ans: B

Topic: Bond-Line Structures
Section: 2.2
Difficulty Level: Medium
17. In the following reaction, how many H’s do you add or lose?
A. Add 1
B. Add 2
C. Lose 1
D. No change
Ans: D
Topic: Bond-Line Structures
Section: 2.2
Difficulty Level: Medium
18. In the following reaction, how many H’s do you add or lose?

A. Add 1
B. Add 2
C. Lose 1
D. No change
Ans: D
Topic: Bond-Line Structures
Section: 2.2
Difficulty Level: Easy
19. In the following reaction, how many H’s do you add or lose?
O

O
OH

A. Add 1
B. Add 2
C. Lose 1
D. No change
Ans: D
Topic: Bond-Line Structures
Section: 2.2
Difficulty Level: Easy
20. In the following reaction, how many H’s do you add or lose?

A. Add 1
B. Add 2
C. Lose 1
D. Lose 2
Ans: D
Topic: Bond-Line Structures
Section: 2.2
Difficulty Level: Easy
21. How many H’s are on the indicated carbon?
A. 1
B. 2
C. 3
D. 4
Ans: C
Topic: Bond-Line Structures
Section: 2.2
Difficulty Level: Easy
22. How many H’s are on the indicated carbon?

A. 1
B. 2
C. 3
D. 0
Ans: D
Topic: Bond-Line Structures
Section: 2.2
Difficulty Level: Easy
23. How many H’s are on the indicated carbon?

A. 1
B. 2
C. 3
D. 4
Ans: B

Topic: Bond-Line Structures
Section: 2.2
Difficulty Level: Medium
24. How many H’s are on the indicated carbon?
A. 1
B. 2
C. 3
D. 4
Ans: A
Topic: Bond-Line Structures
Section: 2.2
Difficulty Level: Medium
25. How many H’s are on the indicated carbon?

A. 1
B. 2
C. 3
D. 0
Ans: D
Topic: Bond-Line Structures
Section: 2.2
Difficulty Level: Medium
26. Convert (CH3CH2CH2)2 into a bond-line structure.
Ans:
Topic: Bond-Line Structures
Section: 2.2
Difficulty Level: Hard
27. Draw bond-line structure for all of the isomers with a molecular formula of C2H4O.
Ans:
O O

Topic: Bond-Line Structures
Section: 2.2
Difficulty Level: Hard
28. Draw bond-line structure for all of the isomers with a molecular formula of C3H8O.

Ans:
OH

OH
Topic: Bond-Line Structures
Section: 2.2
Difficulty Level: Hard
29. Draw a line-bond structure for a compound with a molecular formula of C4H12 and
one carbon with no hydrogens attached to it.
Ans:
Topic: Bond-Line Structures
Section: 2.2
Difficulty Level: Hard
30. Draw a line-bond structure for a compound with a molecular formula of C5H14 and
one carbon with only one hydrogen attached to it.
Ans:
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Easy
31. Which of the following structures contains an alcohol?

1 2 3

4
NH2

OH

A. 1
B. 2
C. 3
D. 4
Ans: C
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Easy
32. Which of the following structures contains an alkene?

1 2 3

4
NH2

A. 1
B. 2
C. 3
D. 4
Ans: C
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Easy
33. Which of the following structures contains an amine?

1 2 3

4
NH2

OH

A. 1
B. 2
C. 3
D. 4
Ans: D
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Easy
34. Which of the following structures contains a ketone?

1 2 3

4

O

O

A. 1
B. 2
C. 3
D. 4
Ans: B
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Easy
35. Which of the following structures contains an aromatic ring?

1 2 3

4

O

O

A. 1
B. 2
C. 3
D. 4
Ans: D
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Easy
36. Which of the following structures contains an alkyne?

1 2 3

4
NH2

OH

A. 1
B. 2
C. 3
D. 4
Ans: B
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Easy
37. Which of the following structures contains a nitrile?

2

1 2 3

4

NH

O
NH2

OH
N O

A. 1
B. 2
C. 3
D. 4
Ans: A
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Easy

38. Which of the following structures contains an amide?

1 2 3

4

NH

O
NH2

OH
N O

A. 1
B. 2
C. 3
D. 4
Ans: B
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Hard
39. Draw all the isomers with a molecular formula of C3H6O and label all the functional
groups.

Ans:

O

O

O

ether

alkene
ketone ether

OH

alcohol
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Hard
40. Draw the isomers with a molecular formula of C4H8O2 and label the functional
groups.
Ans:
O
O

O
O
O
O

O O O
O O

O
O

OH

OH

HO

O O

O
O

O
HO

O
OH

O
OH

O
OH

O
O

ether ether ether

aldehyde

ketone

ester

carboxylic acid

alcohol

ether

ether ether
alcohol

alcohol alcohol alcohol

ester

aldehyde aldehyde

aldehyde aldehyde

ketone ketone

carboxylic acid

O
O
ester

Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Hard

41. Identify the functional groups in the following compound.

N
O
O

OMe
HO HO
OMe

MeO
HO

Ans:

N
O
O

OMe
HO HO
OMe

MeO
HO

ether

ether

ether

ester

alcohol alcohol
alcohol alkene
amine

aromatic ring

aromatic ring
aromatic ring

Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Hard
42. Identify the functional groups in the following compound.

N
S
O
OH

Ans:

N
S
O
OH

sulfide

amide
alcohol

Topic: Formal Charges
Section: 2.4
Difficulty Level: Easy
43. Calculate the formal charge on the indicated atom.
O
H
H

A. +1
B. +2
C. -1
D. -2
Ans: A
Topic: Formal Charges
Section: 2.4
Difficulty Level: Easy
44. Calculate the formal charge on the indicated atom.
N
A. +1
B. +2
C. -1
D. -2
Ans: A
Topic: Formal Charges
Section: 2.4
Difficulty Level: Easy
45. Calculate the formal charge on the indicated atom.
N
A. +1
B. +2
C. -1
D. -2
Ans: A
Topic: Formal Charges
Section: 2.4
Difficulty Level: Easy
46. Calculate the formal charge on the indicated atom.
O
OH
A. +1
B. +2
C. -1
D. 0
Ans: D

Topic: Formal Charges
Section: 2.4
Difficulty Level: Easy
47. Calculate the formal charge on the indicated atom.
N
A. +1
B. +2
C. -1
D. 0
Ans: D
Topic: Formal Charges
Section: 2.4
Difficulty Level: Easy
48. Calculate the formal charge on the indicated atom.
O
A. +1
B. +2
C. -1
D. -2
Ans: A
Topic: Formal Charges
Section: 2.4
Difficulty Level: Easy
49. Determine the number of hydrogens on the indicated atom.
A. 1
B. 2
C. 3
D. 4
Ans: A
Topic: Formal Charges
Section: 2.4
Difficulty Level: Easy
50. Determine the number of hydrogens on the indicated atom.

A. 1
B. 2
C. 3
D. 4
Ans: A
Topic: Formal Charges
Section: 2.4
Difficulty Level: Easy
51. Determine the number of hydrogens on the indicated atom.
A. 1
B. 2
C. 3
D. 0
Ans: D
Topic: Formal Charges
Section: 2.4
Difficulty Level: Medium
52. Determine the formal charges on every atom in the following structure.
N C
Ans:
N C
+1
-1

Topic: Formal Charges
Section: 2.4
Difficulty Level: Hard
53. Draw a valid Lewis structure, with all lone pairs and formal charges for the azide
anion (N3
–
).
Ans:
N N N
+1 -1 -1

Topic: Identifying Lone Pairs
Section: 2.5

Difficulty Level: Easy
54. Determine the number of lone pairs of electrons on the indicated atom.
O
A. 1
B. 2
C. 3
D. 4
Ans: C
Topic: Identifying Lone Pairs
Section: 2.5
Difficulty Level: Easy
55. Determine the number of lone pairs of electrons on the indicated atom.
N
A. 1
B. 2
C. 3
D. 4
Ans: B
Topic: Identifying Lone Pairs
Section: 2.5
Difficulty Level: Easy
56. Determine the number of lone pairs of electrons on the indicated atom.
O
NH2
A. 1
B. 2
C. 3
D. 4
Ans: A
Topic: Identifying Lone Pairs
Section: 2.5
Difficulty Level: Easy
57. Determine the number of lone pairs of electrons on the indicated atom.
O

A. 1
B. 2
C. 3
D. 4
Ans: B
Topic: Identifying Lone Pairs
Section: 2.5
Difficulty Level: Easy
58. Determine the number of lone pairs of electrons on the indicated atom.
O
A. 1
B. 2
C. 3
D. 4
Ans: B
Topic: Identifying Lone Pairs
Section: 2.5
Difficulty Level: Easy
59. Determine the number of lone pairs of electrons on the indicated atom.
O
O OH
A. 1
B. 2
C. 3
D. 4
Ans: B
Topic: Identifying Lone Pairs
Section: 2.5
Difficulty Level: Easy
60. Determine the number of lone pairs of electrons on the indicated atom.
N
A. 1
B. 2
C. 3
D. 4
Ans: A
Topic: Identifying Lone Pairs
Section: 2.5

Difficulty Level: Easy
61. Determine the number of lone pairs of electrons on the indicated atom.
N
A. 1
B. 2
C. 3
D. 4
Ans: B
Topic: Lone Pairs
Section: 2.5
Difficulty Level: Medium
62. Draw all of the lone pairs on the following compound.
O
O
OH
Ans:
O
O
OH

Topic: Lone Pairs
Section: 2.5
Difficulty Level: Medium
63. Draw all of the lone pairs on the following compound.
N
NH2
Ans:
N
NH2

Topic: Three-Dimensional Bond-line Structures
Section: 2.6
Difficulty Level: Easy
64. For the following compound, is the indicated bond up or down?
OH

A. Up
B. Down
Ans: A
Topic: Three-Dimensional Bond-line Structures
Section: 2.6
Difficulty Level: Easy
65. For the following compound, is the indicated bond up or down?

OH
OH
OH
A. Up
B. Down
C. Neither
Ans: C
Topic: Three-Dimensional Bond-line Structures
Section: 2.6
Difficulty Level: Easy
66. For the following compound, is the indicated bond up or down?
O

A. Up
B. Down
C. Neither
Ans: B
Topic: Three-Dimensional Bond-line Structures
Section: 2.6
Difficulty Level: Easy
67. Which of the following structures is the same as structure A?

1 2 3 4
A

A. 1
B. 2

C.