Preview Extract
Klein, Organic Chemistry 3e
Chapter 2
1.
What is the molecular formula for the following compound?
A.
B.
C.
D.
E.
C2H6O
C4H6O
C4H10O
C2H4O
None of these
Answer: C
Learning Objective: 2.1 Convert molecular representations from one drawing style to
another, including Lewis structures, partially condensed structures, condensed
structures, and molecular formulas
Difficulty: Easy
2.
Which of the following compounds have a molecular formula of C2H6O?
A.
B.
C.
D.
E.
I
II
III
IV
Both I and III
Answer: E
Learning Objective: 2.1 Convert molecular representations from one drawing style to
another, including Lewis structures, partially condensed structures, condensed
structures, and molecular formulas
Difficulty: Easy
3.
Which of the following is the correct condensed structure for the following
compound?
A.
B.
C.
D.
E.
CH3CHCH3CH2OH
CH3CH2CH2OH
(CH3)2CHCH2OH
CH3CH2CH2OCH3
CH3CH3CHCH2OH
Answer: C
Learning Objective: 2.1 Convert molecular representations from one drawing style to
another, including Lewis structures, partially condensed structures, condensed
structures, and molecular formulas
Difficulty: Easy
4.
Which of the following is the correct condensed structure for the following
compound?
A.
B.
C.
D.
E.
CH3CHOHCH2CHClCH3
CH3CHOH(CH2)2CHClCH3
(CH3)2CHOHCH2CH2Cl
HOCH3CHCH2CH2CH3CHCl
CH3C2H4CH3OHCl
Answer: B
Learning Objective: 2.1 Convert molecular representations from one drawing style to
another, including Lewis structures, partially condensed structures, condensed
structures, and molecular formulas
Difficulty: Easy
5.
Which of the following is the correct condensed structure for the following
compound?
A.
B.
C.
D.
E.
CH2=CH(CH2)3C(CH3)3
CH(CH2)4C(CH3)3
(CH3)2CH(CH2) 4CH3
CH2CH(CH2)3C(CH3)3
(CH)3(CH2)3C(CH3)3
Answer: A
Learning Objective: 2.1 Convert molecular representations from one drawing style to
another, including Lewis structures, partially condensed structures, condensed
structures, and molecular formulas
Difficulty: Medium
6.
Which of the following is the correct condensed structure for the following
compound?
A.
B.
C.
D.
E.
CH3C2(CH2)3C(CH3)3
CH3CC(CH2)3C(CH3)2CH3
(CH3)3C2(CH2)3CH3
CH3CโกC(CH2)3C(CH3)3
CH3CC(CH2)3C(CH3)3
Answer: D
Learning Objective: 2.1 Convert molecular representations from one drawing style to
another, including Lewis structures, partially condensed structures, condensed
structures, and molecular formulas
Difficulty: Medium
7.
Which of the following is the correct condensed structure for the following
compound?
A.
B.
C.
D.
E.
CH3C(CH3)2(CH2)2(CH)BrC(CH3)2
CH3CH3CH3C(CH2)2C(CH3)2CHBr
(CH3)3C(CH2)3BrCHCH3CH3
CH3CH3CH3C(CH2)2CHBrCHCH3CH3
(CH3)3C(CH2)2CHBrCH(CH3)2
Answer: E
Learning Objective: 2.1 Convert molecular representations from one drawing style to
another, including Lewis structures, partially condensed structures, condensed
structures, and molecular formulas
Difficulty: Medium
8.
Provide the correct condensed structure for the following compound.
Answer: (CH3)3C(CH2)2OCH(CH2CH3)2
Learning Objective: 2.1 Convert molecular representations from one drawing style to
another, including Lewis structures, partially condensed structures, condensed
structures, and molecular formulas
Difficulty: Hard
9.
Provide the correct condensed structure for the following compound.
Answer: (CH3)2N(CH2)3CH(CH3)2
Learning Objective: 2.1 Convert molecular representations from one drawing style to
another, including Lewis structures, partially condensed structures, condensed
structures, and molecular formulas
Difficulty: Hard
10.
Which of the following is the correct molecular formula for (CH3CH2)4C?
A.
B.
C.
D.
E.
C8H20
C5H20
C9H20
C6H5
C3H20
Answer: C
Learning Objective: 2.1 Convert molecular representations from one drawing style to
another, including Lewis structures, partially condensed structures, condensed
structures, and molecular formulas
Difficulty: Easy
11.
Which of the following is the correct Lewis structure for CH3(CH2)2NH2?
A.
B.
C.
D.
E.
I
II
III
IV
Both II and III
Answer: C
Learning Objective: 2.1 Convert molecular representations from one drawing style to
another, including Lewis structures, partially condensed structures, condensed
structures, and molecular formulas
Difficulty: Easy
12.
Which of the following is the correct Lewis structure for CH3(CH2)2OH?
A.
B.
C.
D.
E.
I
II
III
IV
Both II and III
Answer: B
Learning Objective: 2.1 Convert molecular representations from one drawing style to
another, including Lewis structures, partially condensed structures, condensed
structures, and molecular formulas
Difficulty: Easy
13.
Which of the following is the correct Lewis structure for (CH3)2CHCH2OH?
A.
B.
C.
D.
E.
I
II
III
IV
Both III and IV
Answer: C
Learning Objective: 2.1 Convert molecular representations from one drawing style to
another, including Lewis structures, partially condensed structures, condensed
structures, and molecular formulas
Difficulty: Easy
14.
Which of the following is the correct Lewis structure for (CH3)3C(CH2)2NHCH3?
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: D
Learning Objective: 2.1 Convert molecular representations from one drawing style to
another, including Lewis structures, partially condensed structures, condensed
structures, and molecular formulas
Difficulty: Medium
15.
Draw the Lewis structure for CH3CโกC(CH2)3C(CH3)3.
Answer:
Learning Objective: 2.1 Convert molecular representations from one drawing style to
another, including Lewis structures, partially condensed structures, condensed
structures, and molecular formulas
Difficulty: Medium
16.
Draw the Lewis structure for (CH3)3C(CH2)2OCH(CH2CH3)2.
Answer:
Learning Objective: 2.1 Convert molecular representations from one drawing style to
another, including Lewis structures, partially condensed structures, condensed
structures, and molecular formulas
Difficulty: Hard
17.
Identify the partially condensed structure for CH3CH2OCH2CH3.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: A
Learning Objective: 2.1 Convert molecular representations from one drawing style to
another, including Lewis structures, partially condensed structures, condensed
structures, and molecular formulas
Difficulty: Easy
18.
Identify the partially condensed structure for CH3CH2CH2NH2.
Answer: A
Learning Objective: 2.1 Convert molecular representations from one drawing style to
another, including Lewis structures, partially condensed structures, condensed
structures, and molecular formulas
Difficulty: Easy
19.
Which of the following bond-line structures are of the same compound?
A.
B.
C.
D.
E.
I and II
II and III
III and IV
II and IV
None of these
Answer: D
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Easy
20.
Which of the following bond-line structures are of the same compound?
A.
B.
C.
D.
E.
I and III
II and III
III and IV
II and IV
None of these
Answer: A
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Easy
21.
How many hydrogen atoms are connected to the indicated carbon atom?
A.
B.
C.
D.
E.
one
two
three
four
none
Answer: E
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Easy
22.
How many hydrogen atoms are connected to the indicated carbon atom?
A.
B.
one
two
C.
D.
E.
three
four
none
Answer: A
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Easy
23.
How many hydrogen atoms are connected to the indicated carbon atom?
A.
B.
C.
D.
E.
one
two
three
four
none
Answer: B
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Easy
24.
How many hydrogen atoms are connected to the indicated carbon atom?
A.
B.
C.
D.
E.
one
two
three
four
none
Answer: A
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Easy
25.
How many hydrogen atoms are connected to the indicated carbon atom?
A.
B.
C.
D.
E.
one
two
three
four
none
Answer: E
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Easy
26.
For the following equation, how many hydrogen atoms are added or lost?
A.
B.
C.
D.
E.
added one
added two
lost one
lost two
no change
Answer: D
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Easy
27.
For the following equation, how many hydrogen atoms are added or lost?
A.
B.
C.
D.
E.
added one
added two
lost one
lost two
no change
Answer: B
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Easy
28.
For the following equation, how many hydrogen atoms are added or lost?
A.
B.
C.
D.
E.
added one
added two
lost one
lost two
no change
Answer: E
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Easy
29.
For the following equation, how many hydrogen atoms are added or lost?
A.
B.
C.
D.
E.
added one
added two
lost one
lost two
no change
Answer: E
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Easy
30.
For the following equation, how many hydrogen atoms are added or lost?
A.
B.
C.
D.
E.
added one
added two
lost one
lost two
no change
Answer: D
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Medium
31.
For the following equation, how many hydrogen atoms are added or lost?
A.
B.
C.
D.
E.
added one
added two
lost one
lost two
no change
Answer: E
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Medium
32.
Which of the following is the correct Lewis structure for the following compound?
A.
B.
C.
D.
E.
I
II
III
IV
none of these
Answer: B
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Easy
33.
Which of the following is the correct bond-line structure for (CH3)4C?
A.
B.
C.
D.
E.
I
II
III
IV
None of these
Answer: C
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Easy
34.
Which of the following is the correct bond-line structure for (CH3)2CHCH2CH3?
A.
B.
C.
D.
E.
I
II
III
IV
None of these
Answer: A
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Easy
35.
Which of the following
(CH3)2CHCH2C(CH3)3?
A.
B.
C.
D.
E.
I
II
III
IV
None of these
is
the
correct
bond-line
structure
for
Answer: B
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Medium
36.
Which of the following
CH3CโกC(CH2)2CH(CH3)2?
A.
B.
C.
D.
E.
I
II
III
IV
None of these
is
the
correct
bond-line
structure
for
Answer: D
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Medium
37.
Which of the following is
CH3CHOH(CH2)2CH(CH2CH3) 2?
A.
B.
C.
D.
E.
I
II
III
IV
V
the
correct
bond-line
structure
for
Answer: B
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Medium
38.
Draw a bond-line structure for CH3CH2O(CH2)2CH(CH3)2.
Answer:
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Hard
39.
Draw a bond-line structure for (CH3)2N(CH2)3CH(CH3)2.
Answer:
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Hard
40.
Draw a bond-line structure for CH3CโกC(CH2)3C(CH3)2CH2OCH3.
Answer:
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Hard
41.
Draw a bond-line structure for each constitutional isomer with a molecular
formula of C2H4O.
Answer:
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Hard
42.
Draw a bond-line structure for each constitutional isomer with a molecular
formula of C3H8O.
Answer:
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Hard
43.
Provide a condensed structure for the following compound.
Answer: (CH3)3CCH2CH(CH2CH3)(CH2)2CH(CH3)CH2CH3
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Hard
44.
Provide a condensed structure for the following compound.
Answer: (CH3)3C(CH2)2CH(NH2)CH=CHCH3
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Hard
45.
Draw a bond-line structure for each constitutional isomer with molecular formula
C4H10O.
Answer:
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Hard
46.
Draw a bond-line structure for each constitutional isomer with molecular formula
C4H11N.
Answer:
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Medium
47.
Naproxen, sold under the trade name Aleve, has the following structure. What is
the molecular formula for naproxen?
Answer: C14H14O3
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Hard
48.
AZT, used in the treatment of AIDS, has the following structure. What is the
molecular formula for AZT?
Answer: C10H13N5O4
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Hard
49.
Capsaicin, found in peppers, has the following structure. What is the molecular
formula for capsaicin?
Answer: C18H27NO3
Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures
through converting other styles of molecular representation into bond-line structures and
vice versa
Difficulty: Hard
50.
Which of the following compounds contain an alcohol functional group?
A.
B.
C.
D.
E.
I
II
III
IV
None of these
Answer: C
Learning Objective: 2.3 Identify and draw the functional groups
Difficulty: Easy
51.
Which of the following compounds contain an alkene functional group?
A.
B.
C.
D.
E.
I
II
III
IV
None of these
Answer: A
Learning Objective: 2.3 Identify and draw the functional groups
Difficulty: Easy
52.
Which of the following compounds contain an amine functional group?
A.
B.
C.
D.
E.
I
II
III
IV
None of these
Answer: D
Learning Objective: 2.3 Identify and draw the functional groups
Difficulty: Easy
53.
Which of the following compounds contain a ketone functional group?
A.
B.
C.
D.
E.
I
II
III
IV
All of these
Answer: A
Learning Objective: 2.3 Identify and draw the functional groups
Difficulty: Easy
54.
Which of the following compounds contain an aromatic ring?
A.
B.
C.
D.
E.
I
II
III
IV
Both III and IV
Answer: C
Learning Objective: 2.3 Identify and draw the functional groups
Difficulty: Easy
55.
Which of the following compounds contain an ester functional group?
A.
B.
C.
D.
E.
I
II
III
IV
Both I and IV
Answer: A
Learning Objective: 2.3 Identify and draw the functional groups
Difficulty: Easy
56.
Which of the following compounds contain an amide functional group?
A.
B.
C.
D.
E.
I
II
III
IV
Both II and III
Answer: B
Learning Objective: 2.3 Identify and draw the functional groups
Difficulty: Easy
57.
Which of the following compounds contain an anhydride functional group?
A.
B.
C.
D.
E.
I
II
III
IV
none of the above
Answer: C
Learning Objective: 2.3 Identify and draw the functional groups
Difficulty: Easy
58.
Which of the following compounds contain an alkyne functional group?
A.
B.
C.
D.
E.
I
II
III
IV
none of the above
Answer: A
Learning Objective: 2.3 Identify and draw the functional groups
Difficulty: Easy
59.
Which of the following compounds contain a thiol functional group?
A.
B.
C.
D.
E.
I
II
III
IV
none of the above
Answer: B
Learning Objective: 2.3 Identify and draw the functional groups
Difficulty: Easy
60.
Which of the following compounds contain an alkyl halide functional group?
A.
B.
C.
D.
E.
I
II
III
IV
none of the above
Answer: D
Learning Objective: 2.3 Identify and draw the functional groups
Difficulty: Easy
61.
What functional group(s) is (are) present in the following compound?
A.
B.
C.
D.
E.
ketone and alkene
ketone and alkyne
aldehyde and alkene
aldehyde and alkyne
ester and alkene
Answer: C
Learning Objective: 2.3 Identify and draw the functional groups
Difficulty: Medium
62.
Which of the following compounds have both a ketone and an ester functional
group?
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: E
Learning Objective: 2.3 Identify and draw the functional groups
Difficulty: Medium
63.
Norethynodrel, a component of the first combined oral contraceptive, has the
following structure. Identify the functional groups in Norethynodrel.
Answer:
Learning Objective: 2.3 Identify and draw the functional groups
Difficulty: Medium
64.
Identify the functional groups in the following compound.
Answer:
Learning Objective: 2.3 Identify and draw the functional groups
Difficulty: Medium
65.
Tamifluยฎ, the most effective antiviral drug used to treat avian influenza, has the
following structure. Identify the functional groups in Tamifluยฎ.
Answer:
Learning Objective: 2.3 Identify and draw the functional groups
Difficulty: Hard
66.
Aspartame, an artificial sweetener used in Equalยฎ and diet beverages, has the
following structure. Identify the functional groups in Aspartame.
Answer:
Learning Objective: 2.3 Identify and draw the functional groups
Difficulty: Hard
67.
Draw all the constitutional isomers with a molecular formula of C3H6O and label
the functional groups in each isomer.
Answer:
Learning Objective: 2.3 Identify and draw the functional groups
Difficulty: Hard
68.
Amoxicillin, an antibiotic, has the following structure. Identify the functional
groups in amoxicillin.
Answer:
Learning Objective: 2.3 Identify and draw the functional groups
Difficulty: Hard
69.
Viracept, used in the treatment of HIV, has the following structure. Identify the
functional groups in Viracept.
Answer:
Learning Objective: 2.3 Identify and draw the functional groups
Difficulty: Hard
70.
How many hydrogen atoms are connected to the indicated carbon atom?
A.
B.
C.
D.
E.
one
two
three
four
none
Answer: B
Learning Objective: 2.4 Identify formal charges on carbon
Difficulty: Easy
71.
How many hydrogen atoms are connected to the indicated carbon atom?
A.
B.
C.
D.
E.
one
two
three
four
none
Answer: E
Learning Objective: 2.4 Identify formal charges on carbon
Difficulty: Easy
72.
How many hydrogen atoms are connected to the indicated carbon atom?
A.
B.
C.
D.
E.
one
two
three
four
none
Answer: A
Learning Objective: 2.4 Identify formal charges on carbon
Difficulty: Easy
73.
How many hydrogen atoms are connected to the indicated carbon atom?
A.
B.
C.
D.
E.
one
two
three
four
none
Answer: B
Learning Objective: 2.4 Identify formal charges on carbon
Difficulty: Easy
74.
How many hydrogen atoms are connected to the indicated carbon atom?
A.
B.
C.
D.
E.
one
two
three
four
none
Answer: E
Learning Objective: 2.4 Identify formal charges on carbon
Difficulty: Easy
75.
How many hydrogen atoms are connected to the indicated carbon atom?
A.
B.
C.
D.
E.
one
two
three
four
none
Answer: A
Learning Objective: 2.4 Identify formal charges on carbon
Difficulty: Easy
76.
What is the formal charge on the indicated carbon atom?
A.
B.
C.
D.
E.
-2
-1
0
+1
+2
Answer: D
Learning Objective: 2.4 Identify formal charges on carbon
Difficulty: Easy
77.
What is the formal charge on the indicated carbon atom?
A.
B.
C.
D.
E.
-2
-1
0
+1
+2
Answer: D
Learning Objective: 2.4 Identify formal charges on carbon
Difficulty: Easy
78.
What is the formal charge on the indicated carbon atom?
A.
B.
C.
D.
E.
-2
-1
0
+1
+2
Answer: D
Learning Objective: 2.4 Identify formal charges on carbon
Difficulty: Easy
79.
What is the formal charge on the indicated carbon atom?
A.
B.
C.
D.
E.
-2
-1
0
+1
+2
Answer: B
Learning Objective: 2.4 Identify formal charges on carbon
Difficulty: Easy
80.
What is the formal charge on the indicated carbon atom?
A.
-2
B.
C.
D.
E.
-1
0
+1
+2
Answer: B
Learning Objective: 2.4 Identify formal charges on carbon
Difficulty: Easy
81.
What is the formal charge on the indicated carbon atom?
A.
B.
C.
D.
E.
-2
-1
0
+1
+2
Answer: B
Learning Objective: 2.4 Identify formal charges on carbon
Difficulty: Easy
82.
What is the formal charge on the oxygen atom in the following compound?
A.
B.
C.
D.
E.
+1
+2
-1
-2
0
Answer: A
Learning Objective: 2.5 Describe the relationship between the number of bonds, the
number of lone pairs, and formal charge for oxygen and nitrogen atoms
Difficulty: Easy
83.
What is the formal charge on the nitrogen atom in the following compound?
A.
B.
C.
D.
E.
-1
-2
+1
+2
0
Answer: C
Learning Objective: 2.5 Describe the relationship between the number of bonds, the
number of lone pairs, and formal charge for oxygen and nitrogen atoms
Difficulty: Easy
84.
What is the formal charge on the nitrogen atom in the following compound?
A.
B.
C.
D.
E.
+1
+2
-1
-2
0
Answer: A
Learning Objective: 2.5 Describe the relationship between the number of bonds, the
number of lone pairs, and formal charge for oxygen and nitrogen atoms
Difficulty: Easy
85.
What is the formal charge on the indicated oxygen atom in the following
compound?
A.
B.
C.
D.
E.
+1
+2
-1
-2
0
Answer: E
Learning Objective: 2.5 Describe the relationship between the number of bonds, the
number of lone pairs, and formal charge for oxygen and nitrogen atoms
Difficulty: Easy
86.
What is the formal charge on the nitrogen atom in the following compound?
A.
B.
C.
D.
E.
+1
+2
-1
-2
0
Answer: E
Learning Objective: 2.5 Describe the relationship between the number of bonds, the
number of lone pairs, and formal charge for oxygen and nitrogen atoms
Difficulty: Easy
87.
Which of the following compounds have +1 as a formal charge on an oxygen
atom?
A.
B.
I
II
C.
D.
E.
III
IV
Both I and IV
Answer: B
Learning Objective: 2.5 Describe the relationship between the number of bonds, the
number of lone pairs, and formal charge for oxygen and nitrogen atoms
Difficulty: Medium
88.
Which of the following compounds have +1 as a formal charge on the nitrogen
atom?
A.
B.
C.
D.
E.
I
II
III
IV
Both I and II
Answer: D
Learning Objective: 2.5 Describe the relationship between the number of bonds, the
number of lone pairs, and formal charge for oxygen and nitrogen atoms
Difficulty: Medium
89.
Determine the formal charges on each atom except hydrogen.
Answer:
Learning Objective: 2.5 Describe the relationship between the number of bonds, the
number of lone pairs, and formal charge for oxygen and nitrogen atoms
Difficulty: Medium
90.
Diazomethane has the molecular formula CH2N2. Draw the preferred Lewis
structure for diazomethane and assign formal charges to all atoms except
hydrogen.
Answer:
Learning Objective: 2.5 Describe the relationship between the number of bonds, the
number of lone pairs, and formal charge for oxygen and nitrogen atoms
Difficulty: Hard
91.
Draw Lewis structure for the following compound.
Answer:
Learning Objective: 2.5 Describe the relationship between the number of bonds, the
number of lone pairs, and formal charge for oxygen and nitrogen atoms
Difficulty: Medium
92.
How many lone pairs of electrons are on the oxygen atom?
A.
B.
C.
D.
E.
one
two
three
four
none
Answer: C
Learning Objective: 2.5 Describe the relationship between the number of bonds, the
number of lone pairs, and formal charge for oxygen and nitrogen atoms
Difficulty: Easy
93.
How many lone pairs of electrons are on the nitrogen atom?
A.
B.
C.
D.
E.
one
two
three
four
none
Answer: B
Learning Objective: 2.5 Describe the relationship between the number of bonds, the
number of lone pairs, and formal charge for oxygen and nitrogen atoms
Difficulty: Easy
94.
How many lone pairs of electrons are on the oxygen atom?
A.
B.
C.
D.
E.
one
two
three
four
none
Answer: B
Learning Objective: 2.5 Describe the relationship between the number of bonds, the
number of lone pairs, and formal charge for oxygen and nitrogen atoms
Difficulty: Easy
95.
How many lone pairs of electrons are on the nitrogen atom?
A.
B.
C.
D.
E.
one
two
three
four
none
Answer: A
Learning Objective: 2.5 Describe the relationship between the number of bonds, the
number of lone pairs, and formal charge for oxygen and nitrogen atoms
Difficulty: Easy
96.
How many lone pairs of electrons are on the nitrogen atom?
A.
B.
C.
D.
E.
one
two
three
four
none
Answer: E
Learning Objective: 2.5 Describe the relationship between the number of bonds, the
number of lone pairs, and formal charge for oxygen and nitrogen atoms
Difficulty: Easy
97.
How many lone pairs of electrons are on the indicated oxygen atom?
A.
B.
C.
D.
E.
one
two
three
four
none
Answer: B
Learning Objective: 2.5 Describe the relationship between the number of bonds, the
number of lone pairs, and formal charge for oxygen and nitrogen atoms
Difficulty: Easy
98.
How many lone pairs of electrons are on the indicated oxygen atom?
A.
B.
C.
D.
E.
one
two
three
four
none
Answer: A
Learning Objective: 2.5 Describe the relationship between the number of bonds, the
number of lone pairs, and formal charge for oxygen and nitrogen atoms
Difficulty: Medium
99.
How many total lone pairs of electrons are in the following compound?
A.
B.
C.
D.
E.
one
two
three
four
none
Answer: C
Learning Objective: 2.5 Describe the relationship between the number of bonds, the
number of lone pairs, and formal charge for oxygen and nitrogen atoms
Difficulty: Easy
100.
Draw all lone pairs of electrons for the following compound.
Answer:
Learning Objective: 2.5 Describe the relationship between the number of bonds, the
number of lone pairs, and formal charge for oxygen and nitrogen atoms
Difficulty: Medium
101.
Draw all lone pairs of electrons for the following compound.
Answer:
Learning Objective: 2.5 Describe the relationship between the number of bonds, the
number of lone pairs, and formal charge for oxygen and nitrogen atoms
Difficulty: Medium
102.
The indicated bond in the following compound is_____ of the paper.
A.
B.
C.
D.
in the plane
out of the plane
behind the plane
None of these
Answer: B
Learning Objective: 2.6 Describe how wedges and dashes are used to indicate threedimensional molecular structure
Difficulty: Easy
103.
The indicated bond in the following compound is_____ of the paper.
A.
B.
C.
D.
in the plane
out of the plane
behind the plane
None of these
Answer: C
Learning Objective: 2.6 Describe how wedges and dashes are used to indicate threedimensional molecular structure
Difficulty: Easy
104.
The indicated bond in the following compound is_____ of the paper.
A.
B.
C.
D.
in the plane
out of the plane
behind the plane
None of these
Answer: C
Learning Objective: 2.6 Describe how wedges and dashes are used to indicate threedimensional molecular structure
Difficulty: Easy
105.
Which of the following is a Fischer projection?
A.
B.
C.
D.
E.
I
II
III
IV
Both III and IV
Answer: B
Learning Objective: 2.6 Describe how wedges and dashes are used to indicate threedimensional molecular structure
Difficulty: Easy
106.
Which of the following is a Haworth projection?
A.
B.
C.
D.
E.
I
II
III
IV
Both III and IV
Answer: C
Learning Objective: 2.6 Describe how wedges and dashes are used to indicate threedimensional molecular structure
Difficulty: Easy
107.
Label the bonds that are out of the plane and behind the plane of the paper.
Answer:
Learning Objective: 2.6 Describe how wedges and dashes are used to indicate threedimensional molecular structure
Difficulty: Medium
108.
Which of the following pairs are resonance structures of each other?
A.
B.
C.
D.
E.
I
II
III
IV
None of these
Answer: D
Learning Objective: 2.7 Define “resonance,” describing the relationship between
resonance and molecular orbital theory
Difficulty: Easy
109.
Which of the following pairs are resonance structures of each other?
A.
B.
C.
D.
E.
I
II
III
IV
None of these
Answer: C
Learning Objective: 2.7 Define “resonance,” describing the relationship between
resonance and molecular orbital theory
Difficulty: Easy
110.
The spreading of positive or negative charge over two or more atoms in a
compound is called_______.
A.
B.
C.
D.
E.
isomerism
delocalization
stereoisomerism
localization
None of these
Answer: B
Learning Objective: 2.7 Define “resonance,” describing the relationship between
resonance and molecular orbital theory
Difficulty: Easy
111.
Delocalization of charge over two or more atoms _______ a molecule.
A.
B.
C.
D.
E.
destabilizes
delocalizes
localizes
stabilizes
None of these
Answer: D
Learning Objective: 2.7 Define “resonance,” describing the relationship between
resonance and molecular orbital theory
Difficulty: Easy
112.
Resonance structures have _______ connectivity of atoms and _______
distribution of electrons.
A.
B.
C.
D.
E.
different, same
same, same
different, different
same, different
None of these
Answer:
D
Learning Objective: 2.7 Define “resonance,” describing the relationship between
resonance and molecular orbital theory
Difficulty: Medium
113.
What is a resonance hybrid?
Answer: A molecule that can be represented by drawing two or more resonance
structures is viewed as a resonance hybrid.
Learning Objective: 2.7 Define “resonance,” describing the relationship between
resonance and molecular orbital theory
Difficulty: Medium
114.
Which of the following violates the rules for curved arrows?
A.
B.
C.
D.
E.
I
II
III
IV
none of these
Answer: A
Learning Objective: 2.8 Demonstrate the used of curved arrows in drawing resonance
structures, stating the two rules to be applied when drawing curved arrows
Difficulty: Easy
115.
Which of the following violates the rules for curved arrows?
A.
B.
C.
D.
E.
I
II and IV
I and III
III and IV
None of these
Answer: C
Learning Objective: 2.8 Demonstrate the used of curved arrows in drawing resonance
structures, stating the two rules to be applied when drawing curved arrows
Difficulty: Easy
116.
Which of the following violates the rules for curved arrows?
A.
B.
C.
D.
E.
I and II
III and IV
I, and III
II, III and IV
all of these
Answer: C
Learning Objective: 2.8 Demonstrate the used of curved arrows in drawing resonance
structures, stating the two rules to be applied when drawing curved arrows
Difficulty: Easy
117.
Provide the curved arrow(s) to draw a resonance structure for the following
compound.
Answer:
Learning Objective: 2.8 Demonstrate the used of curved arrows in drawing resonance
structures, stating the two rules to be applied when drawing curved arrows
Difficulty: Medium
118.
Provide the curved arrow(s) to draw a resonance structure for the following
compound.
Answer:
Learning Objective: 2.8 Demonstrate the used of curved arrows in drawing resonance
structures, stating the two rules to be applied when drawing curved arrows
Difficulty: Medium
119.
Provide the curved arrow(s) to draw a resonance structure for the following
compound.
Answer:
Learning Objective: 2.8 Demonstrate the used of curved arrows in drawing resonance
structures, stating the two rules to be applied when drawing curved arrows
Difficulty: Hard
120.
Explain using words as well as structural drawings, if the single curved arrow
shown is sufficient to draw the resonance structure.
Answer:
The single arrow shown will violate the octet rule. Drawing another curved
arrow will remove the violation.
Learning Objective: 2.8 Demonstrate the used of curved arrows in drawing resonance
structures, stating the two rules to be applied when drawing curved arrows
Difficulty: Hard
121.
Draw the resonance structure indicated by the curved arrows.
Answer:
Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in
resonance structures
Difficulty: Medium
122.
Draw the resonance structure indicated by the curved arrows.
Answer:
Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in
resonance structures
Difficulty: Medium
123.
Draw the resonance structure indicated by the curved arrows.
Answer:
Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in
resonance structures
Difficulty: Medium
124.
Draw the resonance structure indicated by the curved arrows.
Answer:
Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in
resonance structures
Difficulty: Medium
125.
Draw the curved arrow(s) for converting the first resonance structure into the
second resonance structure.
Answer:
Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in
resonance structures
Difficulty: Medium
126.
Draw the curved arrow(s) for converting the first resonance structure into the
second resonance structure.
Answer:
Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in
resonance structures
Difficulty: Hard
127.
Draw the curved arrow(s) for converting the first resonance structure into the
second resonance structure.
Answer:
Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in
resonance structures
Difficulty: Hard
128.
Draw the curved arrow(s) for converting the first resonance structure into the
second resonance structure.
Answer:
Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in
resonance structures
Difficulty: Hard
129.
Which of the following is a correct resonance structure for compound A?
A.
B.
C.
D.
E.
I
II
III
IV
none of these
Answer: D
Learning Objective: 2.10 Identify resonance structures by naming the five different
structural patterns in molecules
Difficulty: Easy
130.
Which of the following is a correct resonance structure for compound A?
A.
B.
C.
D.
E.
I
II
III
IV
None of these
Answer: C
Learning Objective: 2.10 Identify resonance structures by naming the five different
structural patterns in molecules
Difficulty: Medium
131.
Which of the following is/are correct resonance structure(s) for compound A?
A.
B.
C.
D.
E.
I
II and III
III and IV
I and III
I and IV
Answer: B
Learning Objective: 2.10 Identify resonance structures by naming the five different
structural patterns in molecules
Difficulty: Easy
132.
Which of the following is/are correct resonance structure(s) for compound A?
A.
B.
C.
D.
I and II
II and III
III and IV
I and III
E.
I and IV
Answer: C
Learning Objective: 2.10 Identify resonance structures by naming the five different
structural patterns in molecules
Difficulty: Medium
133.
Which of the following is a correct resonance structure for compound A?
A.
B.
C.
D.
E.
I
II
III
IV
none of these
Answer: A
Learning Objective: 2.10 Identify resonance structures by naming the five different
structural patterns in molecules
Difficulty: Easy
134.
Which of the following is/are correct resonance structure(s) for compound A?
A.
B.
C.
D.
E.
I and II
II and III
III and IV
I, II and III
I and IV
Answer: D
Learning Objective: 2.10 Identify resonance structures by naming the five different
structural patterns in molecules
Difficulty: Medium
135.
Which of the following is a correct resonance structure for compound A?
A.
B.
C.
D.
E.
I
II
III
IV
None of these
Answer: C
Learning Objective: 2.10 Identify resonance structures by naming the five different
structural patterns in molecules
Difficulty: Easy
136.
Which of the following is a correct resonance structure for compound A?
A.
B.
C.
D.
E.
I
II
III
IV
None of these
Answer: B
Learning Objective: 2.10 Identify resonance structures by naming the five different
structural patterns in molecules
Difficulty: Easy
137.
Which of the following is a correct resonance structure for compound A?
A.
B.
C.
D.
E.
I
II
III
IV
none of these
Answer: A
Learning Objective: 2.10 Identify resonance structures by naming the five different
structural patterns in molecules
Difficulty: Medium
138.
Draw resonance structures for the following compound.
Answer:
Learning Objective: 2.10 Identify resonance structures by naming the five different
structural patterns in molecules
Difficulty: Medium
139.
Draw two resonance structures for HN3.
Answer:
Learning Objective: 2.10 Identify resonance structures by naming the five different
structural patterns in molecules
Difficulty: Hard
140.
Draw two additional resonance structures for the following compound.
Answer:
Learning Objective: 2.10 Identify resonance structures by naming the five different
structural patterns in molecules
Difficulty: Hard
141.
Draw two additional resonance structures for the following compound.
Answer:
Learning Objective: 2.10 Identify resonance structures by naming the five different
structural patterns in molecules
Difficulty: Hard
142.
Which of the following is/are the most significant resonance structure(s)?
A.
B.
C.
D.
E.
I
II
III
II and III
all of these
Answer: C
Learning Objective: 2.11 Distinguish between significant and insignificant resonance
structures, describing how the significance of resonance is determined
Difficulty: Easy
143.
Which of the following is/are the most significant resonance structure(s)?
A.
B.
C.
D.
E.
I
II
III
I and II
all of these
Answer: B
Learning Objective: 2.11 Distinguish between significant and insignificant resonance
structures, describing how the significance of resonance is determined Difficulty: Easy
144.
Which of the following is/are the most significant resonance structure(s)?
A.
B.
C.
D.
E.
I
II
III
I and II
all of these
Answer: C
Learning Objective: 2.11 Distinguish between significant and insignificant resonance
structures, describing how the significance of resonance is determined Difficulty:
Medium
145.
Which of the following is/are the most significant resonance structure(s)?
A.
B.
C.
D.
I
II
III
I and II
E.
I and IV
Answer: C
Learning Objective: 2.11 Distinguish between significant and insignificant resonance
structures, describing how the significance of resonance is determined
Difficulty: Medium
146.
Which of the following is the most significant resonance structure?
A.
B.
C.
D.
E.
I
II
III
IV
None of these
Answer: C
Learning Objective: 2.11 Distinguish between significant and insignificant resonance
structures, describing how the significance of resonance is determined
Difficulty: Medium
147.
Which of the following is/are the most significant resonance structure(s)?
A.
B.
I
II
C.
D.
E.
III
I and III
all of these
Answer: B
Learning Objective: 2.11 Distinguish between significant and insignificant resonance
structures, describing how the significance of resonance is determined
Difficulty: Medium
148.
Draw significant resonance structures for the following compound, CH3CNO.
Which of these is/are the most significant resonance structure(s)? Explain why.
Answer:
Resonance structure II is most significant, because the more electronegative oxygen
atom carries a negative formal charge.
Learning Objective: 2.11 Distinguish between significant and insignificant resonance
structures, describing how the significance of resonance is determined
Difficulty: Hard
149.
Draw significant resonance structures for the following compound. Which of
these is/are the most significant resonance structure(s)? Explain why.
Answer:
Resonance structure III is most significant, because all atoms have octet of electrons.
Learning Objective: 2.11 Distinguish between significant and insignificant resonance
structures, describing how the significance of resonance is determined
Difficulty: Hard
150.
Draw significant resonance structures for N2O. Which of these is/are the most
significant resonance structure(s)? Explain why.
Answer:
Resonance structure III is most significant, because the more electronegative oxygen
atom carries a negative formal charge.
Learning Objective: 2.11 Distinguish between significant and insignificant resonance
structures, describing how the significance of resonance is determined
Difficulty: Hard
151.
What is the relationship between the following compounds?
A.
B.
C.
D.
constitutional isomers
resonance structures
conformers
identical compounds
Answer: B
Learning Objective: 2.11 Distinguish between significant and insignificant resonance
structures, describing how the significance of resonance is determined
Difficulty: Easy
152.
What is the relationship between the following compounds?
A.
B.
C.
D.
constitutional isomers
resonance structures
conformers
identical compounds
Answer: A
Learning Objective: 2.11 Distinguish between significant and insignificant resonance
structures, describing how the significance of resonance is determined
Difficulty: Easy
153.
What is the relationship between the following compounds?
A.
B.
C.
D.
E.
constitutional isomers
resonance structures
conformers
identical compounds
different compounds
Answer: B
Learning Objective: Assessing Importance
Section: 2.11
Difficulty: Easy
154.
What is the relationship between the following compounds?
A.
B.
C.
D.
E.
constitutional isomers
resonance structures
conformers
identical compounds
different compounds
Answer: B
Learning Objective: 2.11 Distinguish between significant and insignificant resonance
structures, describing how the significance of resonance is determined
Difficulty: Easy
155.
Draw the resonance hybrid of C6H6.
Answer:
Learning Objective: 2.12 Draw a resonance hybrid using partial bonds and partial
charges, reflecting the combination of individual resonance structures
Difficulty: Medium
156.
Draw the resonance hybrid of CH2CHCHCHCH2+.
Answer:
Learning Objective: 2.12 Draw a resonance hybrid using partial bonds and partial
charges, reflecting the combination of individual resonance structures
Difficulty: Medium
157.
Draw the resonance hybrid for the following structure.
Answer:
Learning Objective: 2.12 Draw a resonance hybrid using partial bonds and partial
charges, reflecting the combination of individual resonance structures
Difficulty: Medium
158.
The lone pair on nitrogen in the following compound is _______.
A.
B.
localized
delocalized
Answer: A
Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and
describe how delocalized lone pairs participate in resonance and why localized lone
pairs do not participate in resonance
Difficulty: Easy
159.
The lone pair on oxygen in the following compound is _______.
A.
B.
C.
both localized
both delocalized
one localized and one delocalized
Answer: C
Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and
describe how delocalized lone pairs participate in resonance and why localized lone
pairs do not participate in resonance
Difficulty: Easy
160.
The lone pair on nitrogen in the following compound is _______.
A.
B.
localized
delocalized
Answer: A
Learning Objective: 2.12 Distinguish between delocalized and localized lone pairs and
describe how delocalized lone pairs participate in resonance and why localized lone
pairs do not participate in resonance
Difficulty: Easy
161.
The lone pairs on oxygen in the following compound are _______.
A.
B.
both localized
both delocalized
C.
one localized and one delocalized
Answer: C
Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and
describe how delocalized lone pairs participate in resonance and why localized lone
pairs do not participate in resonance
Difficulty: Easy
162.
The lone pairs on nitrogen in the following compound are _______.
A.
B.
C.
D.
three localized
three delocalized
two localized and one delocalized
one localized and two delocalized
Answer: A
Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and
describe how delocalized lone pairs participate in resonance and why localized lone
pairs do not participate in resonance
Difficulty: Easy
163.
For the following compound identify the lone pairs and indicate if each lone pair
is localized or delocalized.
Answer:
Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and
describe how delocalized lone pairs participate in resonance and why localized lone
pairs do not participate in resonance
Difficulty: Medium
164.
For the following compound identify the lone pairs and indicate if each lone pair
is localized or delocalized.
Answer:
Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and
describe how delocalized lone pairs participate in resonance and why localized lone
pairs do not participate in resonance
Difficulty: Medium
165.
For the following compound identify the lone pairs and indicate if each lone pair
is localized or delocalized.
Answer:
Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and
describe how delocalized lone pairs participate in resonance and why localized lone
pairs do not participate in resonance
Difficulty: Medium
166.
For the following compound what is the hybridization state and molecular
geometry at each oxygen and nitrogen atom.
Answer:
Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and
describe how delocalized lone pairs participate in resonance and why localized lone
pairs do not participate in resonance
Difficulty: Hard
167.
Caffeine has the following structure. What is the hybridization state and
molecular geometry at each nitrogen atom in caffeine?
Answer:
Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and
describe how delocalized lone pairs participate in resonance and why localized lone
pairs do not participate in resonance
Difficulty: Hard
168.
Enalapril, is a drug used in the treatment of heart disease. What is the
hybridization state and molecular geometry at the indicated atoms in Enalapril?
Answer:
Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and
describe how delocalized lone pairs participate in resonance and why localized lone
pairs do not participate in resonance
Difficulty: Hard
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