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Preview Extract
Chapter Two
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Easy
1. What is the molecular formula for the following compound?
H
H
H
C
C
H
H
O
H
H
C
C
H
H
H
A) C2H6O
B) C4H6O
C) C4H10O
D) C2H4O
E) None of these
Ans: C
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Easy
2. Which of the following compounds have a molecular formula of C2H6O?
CH3OCH3
CH3CH2OCH3
CH3CH2OH
I
II
III
A) I
B) II
C) III
D) IV
E) Both I & III
Ans: E
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Easy
CH3CHOHCH3
IV
3. Which of the following is the correct condensed structure for the following compound?
H
H
H
C
H
C
H
H
C
H
O
C
H
H
H
A) CH3CH3CH2OH
B) CH3CH2CH2OH
C) (CH3)2CHCH2OH
D) CH3CH2CH2OCH3
E) CH3C2H3CH3OH
Ans: C
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Easy
4. Which of the following is the correct condensed structure for the following compound?
H
H
H
H
H
Cl
H
C
C
C
C
C
C
H
O
H
H
H
H
H
A) CH3CHOHCH2CHClCH3
B) CH3CHOH(CH2)2CHClCH3
C) (CH3)2CHOHCH2CH2Cl
D) CH3CHCH2CH2OHCH3CHCl
E) CH3C2H4CH3OHCl
Ans: B
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Medium
H
5. Which of the following is the correct condensed structure for the following compound?
A) CH2=CH(CH2)3C(CH3)3
B) CH(CH2)4C(CH3)3
C) (CH3)2CH(CH2)4CH3
D) CH2CH(CH2)3C(CH3)3
E) (CH)3(CH2)3C(CH3)3
Ans: A
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Medium
6. Which of the following is the correct condensed structure for the following compound?
H
H
H
C
H
C
C
H
H
H
H
H
C
H
C
C
C
C
C
H
H
H
C
H
A) CH3C2(CH2)3C(CH3)3
B) CH3CC(CH2)3C(CH3)2CH3
C) (CH3)3C2(CH2)3CH3
D) CH3C๏บC(CH2)3C(CH3)3
E) CH3CC(CH2)3C(CH3)3
Ans: D
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Medium
H
H
H
H
7. Which of the following is the correct condensed structure for the following compound?
H
H
H
H
H
H
H
H
C
H
H
H
C
H
C
C
C
C
C
C
C
H
C
H
H
Br
H
H
H
H
H
H
A) CH3C(CH3)2(CH2)2(CH)BrC(CH3)2
B) CH3CH3CH3C(CH2)2C(CH3)2CHBr
C) (CH3)3C(CH2)3BrCHCH3CH3
D) CH3CH3CH3C(CH2)2CHBrCHCH3CH3
E) (CH3)3C(CH2)2CHBrCH(CH3)2
Ans: E
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Hard
8. Provide correct condensed structure for the following compound.
H
H
H
H
H
H
H
H
C
H
H
C
C
C
C
H
C
H
H
H
H
O
H
C
H
C
H
H
C
C
C
H
H
H
H
H
Ans: (CH3)3C(CH2)2OCH(CH2CH3)2
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Hard
9. Provide correct condensed structure for the following compound.
H
H
H
H
H
H
H
H
C
H
C
N
C
C
C
C
C
H
C
H
H
H
H
H
H
H
H
Ans: (CH3)2N(CH2)3CH(CH3)2
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Easy
H
10. Which of the following is the correct molecular formula for (CH3CH2)4C?
A) C8H20
B) C5H20
C) C9H20
D) C6H5
E) C3H20
Ans: C
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Easy
11. Which of the following is the correct Lewis structure for CH3(CH2)2NH2?
H
H
H
C
C
N
H
H
H
H
H
H
H
H
C
C
C
N
H
H
H
H
I
H
H
H
H
H
C
C
C
N
H
H
H
H
H
CH3CH2CH2NH2
IV
III
II
A) I
B) II
C) III
D) IV
E) Both II & III
Ans: C
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Easy
12. Which of the following is the correct Lewis structure for CH3(CH2)2OH?
H
H
H
C
C
H
H
O
H
H
H
H
H
C
C
C
H
H
H
I
A) I
B) II
C) III
D) IV
E) Both II & III
Ans: B
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Easy
II
O
H
H
H
H
H
C
C
C
H
H
H
III
O
H
CH3CH2CH2OH
IV
13. Which of the following is the correct Lewis structure for (CH3)2CHCH2OH?
H
H
H
H
H
C
C
C
C
H
H
H
H
H
H
H C H
H
O
H
H
H
H
H
H
C
C
C
C
H
H
H
H
O
H
H
C
H
C
H
H
O
H
H
C
H
C
C
H
H
IV
III
II
I
C
H
H
H
H C H
A) I
B) II
C) III
D) IV
E) Both III & IV
Ans: C
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Medium
14. Which of the following is the correct Lewis structure for (CH3)3C(CH2)2NHCH3?
H
H
H
H
H
H
C
H
C
C
C
C
N
C
H
C
H
H
H
H
H
H H
H
H
H
H
HH
H
C
H
H
H
C
C
C
C
C
N
H
H
C
H
H
H
H
I
H
H
H
H H
HH
H
C
H
H
H
C
C
C
C
N
C
H
C
H
H
H
H
H
HH
IV
A) I
B) II
C) III
D) IV
E) V
Ans: D
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Medium
H
H
H
H
C
H
C
C
C
C
N
H
C
H
H
H
H
H H III
H
H
H
H
H
C
C
C
C
C
N
C
H
H
C
H
H
H
H
H
HH
V
H
H
II
H
H
H
H
CH3
OH
15. Draw the Lewis structure for CH3C๏บC(CH2)3C(CH3)3.
H
Ans:
H
H
H
H
C
C
C
H
H
H
H
C
H
C
C
C
C
C
H
H
H
C
H
H
H
H
H
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Hard
16. Draw the Lewis structure for (CH3)3C(CH2)2OCH(CH2CH3)2.
H
Ans:
H
H
H
H
H
H
H
H
C
H
H
C
C
C
C
H
C
H
H
H
H
O
C
H
C
H
H
C
C
C
H
H
H
H
H
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
17. Which of the following bond-line structures are of the same compound?
I
A) I & II
B) II & III
C) III & IV
D) II & IV
E) None of these
Ans: D
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
II
III
IV
18. Which of the following bond-line structures are of the same compound?
I
II
III
A) I & III
B) II & III
C) III & IV
D) II & IV
E) None of these
Ans: A
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
19. How many H atoms are connected to the indicated carbon atom?
A) one
B) two
C) three
D) four
E) none
Ans: E
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
20. How many H atoms are connected to the indicated carbon atom?
A) one
B) two
C) three
D) four
E) none
Ans: A
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
IV
21. How many H atoms are connected to the indicated carbon atom?
A) one
B) two
C) three
D) four
E) none
Ans: B
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
22. How many H atoms are connected to the indicated carbon atom?
A) one
B) two
C) three
D) four
E) none
Ans: A
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
23. How many H atoms are connected to the indicated carbon atom?
A) one
B) two
C) three
D) four
E) none
Ans: E
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
24. For the following transformation how many H atoms are added or lost?
A) Added one
B) Added two
C) Lost one
D) Lost two
E) No change
Ans: D
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
25. For the following transformation how many H atoms are added or lost?
O
OH
A) Added one
B) Added two
C) Lost one
D) Lost two
E) No change
Ans: B
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
26. For the following transformation how many H atoms are added or lost?
A) Added one
B) Added two
C) Lost one
D) Lost two
E) No change
Ans: E
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
27. For the following transformation how many H atoms are added or lost?
OH
O
O
A) Added one
B) Added two
C) Lost one
D) Lost two
E) No change
Ans: E
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Medium
28. For the following transformation how many H atoms are added or lost?
OH
A) Added one
B) Added two
C) Lost one
D) Lost two
E) No change
Ans: D
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Medium
29. For the following transformation how many H atoms are added or lost?
A) Added one
B) Added two
C) Lost one
D) Lost two
E) No change
Ans: E
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
30. Which of the following is the correct Lewis structure for the following compound?
O
H
H
C
H
O
C
H
C
H
H
I
II
A) I
B) II
C) III
D) IV
E) None of these
Ans: B
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
H
O
C
H
H
O
C
H
C
O
H
III
H
O
C
C
H
H
IV
H
31. Which of the following is the correct bond-line structure for (CH3)4C?
I
IV
III
II
A) I
B) II
C) III
D) IV
E) None of these
Ans: C
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
32. Which of the following is the correct bond-line structure for (CH3)2CHCH2CH3?
I
IV
III
II
A) I
B) II
C) III
D) IV
E) None of these
Ans: A
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Medium
33. Which of the following is the correct bond-line structure for (CH3)2CHCH2C(CH3)3?
I
A) I
B) II
C) III
D) IV
E) None of these
Ans: B
Topic: Bond Line Structure
Section: 2.2
II
III
IV
Difficulty Level: Medium
34. Which of the following is the correct bond-line structure for CH3C๏บC(CH2)2CH(CH3)2?
I
III
II
IV
A) I
B) II
C) III
D) IV
E) None of these
Ans: D
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Medium
35. Which of the following is the correct bond-line structure for
CH3CHOH(CH2)2CH(CH2CH3)2?
OH
OH
O
O
O
I
II
III
A) I
B) II
C) III
D) IV
E) V
Ans: B
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Medium
36. Draw a bond-line structure for CH3CH2O(CH2)2CH(CH3)2.
Ans:
O
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Hard
IV
V
37. Draw a bond-line structure for (CH3)2N(CH2)3CH(CH3)2.
Ans:
N
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Hard
38. Draw a bond-line structure for CH3C๏บC(CH2)3C(CH3)2CH2OCH3.
Ans:
O
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Hard
39. Draw a bond-line structure for each constitutional isomer with a molecular formula of
C2H4O.
H
Ans:
O
O
O
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Hard
40. Draw a bond-line structure for each constitutional isomer with a molecular formula of
C3H8O.
Ans:
OH
OH
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Hard
O
41. Provide a condensed structure for the following compound.
Ans: (CH3)3CCH2CH(CH2CH3)(CH2)2CH(CH3)CH2CH3
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Hard
42. Provide a condensed structure for the following compound.
NH2
Ans: (CH3)3C(CH2)2CH(NH2)CH=CHCH3
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Hard
43. Draw a bond-line structure for each constitutional isomer with molecular formula
C4H10O.
Ans:
OH
OH
OH
OH
O
O
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Hard
O
44. Draw a bond-line structure for each constitutional isomer with molecular formula
C4H11N.
Ans:
NH2
NH2
NH2
NH2
H
N
N
N
H
N
H
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Medium
45. Naproxen, sold under the trade name Aleve, has the following structure. What is the
molecular formula for naproxen?
OH
O
O
Ans: C14H14O3
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Hard
46. AZT, used in the treatment of AIDS, has the following structure. What is the molecular
formula for AZT?
O
O
N
HO
NH
O
N3
Ans: C10H13N5O4
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Hard
47. Capsaicin, found in peppers, has the following structure. What is the molecular formula
for capsaicin?
H
N
O
O
OH
Ans: C18H27NO3
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Easy
48. Which of the following compounds contain an alcohol functional group?
NH2
O
OH
I
II
IV
III
A) I
B) II
C) III
D) IV
E) None of these
Ans: C
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Easy
49. Which of the following compounds contain an alkene functional group?
NH2
I
II
A) I
B) II
C) III
D) IV
E) None of these
Ans: A
Topic: Identifying Functional Groups
Section: 2.3
III
IV
Difficulty Level: Easy
50. Which of the following compounds contain an amine functional group?
NH2
O
OH
I
II
IV
III
A) I
B) II
C) III
D) IV
E) None of these
Ans: D
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Easy
51. Which of the following compounds contain a ketone functional group?
O
O
O
O
HO
O
I
II
A) I
B) II
C) III
D) IV
E) All of these
Ans: A
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Easy
III
IV
52. Which of the following compounds contain an aromatic ring?
O
I
II
III
IV
A) I
B) II
C) III
D) IV
E) Both III & IV
Ans: C
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Easy
53. Which of the following compounds contain an ester functional group?
O
O
N
N
O
I
II
O
IV
III
A) I
B) II
C) III
D) IV
E) Both I & IV
Ans: A
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Easy
54. Which of the following compounds contain an amide functional group?
O
O
N
N
N
O
I
II
A) I
B) II
C) III
D) IV
E) Both II & III
Ans: B
Topic: Identifying Functional Groups
Section: 2.3
C
III
IV
Difficulty Level: Medium
55. What functional group(s) is (are) present in the following compound?
O
A) ketone & alkene
B) ketone & alkyne
C) aldehyde & alkene
D) aldehyde & alkyne
E) ester & alkene
Ans: C
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Medium
56. Which of the following compounds have both a ketone and an ester functional group?
O
O
O
O
I
II
A) I
B) II
C) III
D) IV
E) V
Ans: E
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Medium
OH
O
O
O
O
O
O
III
OH
IV
OH
V
O
57. Norethynodrel, a component of the first combined oral contraceptive, has the following
structure. Identify the functional groups in Norethynodrel.
OH
O
alcohol
Ans:
OH
alkyne
ketone
O
alkene
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Medium
58. Identify the functional groups in the following compound.
OH
S
N
O
Ans:
OH
alcohol
S
N
O
amide
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Hard
sulfide
59. Tamifluยฎ, is the most effective antiviral drug used to treat avian influenza, has the
following structure. Identify the functional groups in Tamifluยฎ.
O
O
O
O
N
H
NH2
alkene
Ans:
O
ether
O
O
O
ester
N
H
NH2
amide
amine
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Hard
60. Aspartame, an artificial sweetener used in Equalยฎ and diet beverages, has the following
structure. Identify the functional groups in Aspartame.
NH2
O
H
N
OH
O
O
O
Ans:
amine
aromatic
amide
NH2
O
H
N
OH
O
O
ester
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Hard
O
carboxylic acid
61. Draw all the constitutional isomers with a molecular formula of C3H6O and label the
functional groups in each isomer.
Ans:
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Hard
62. Amoxicillin, an antibiotic, has the following structure. Identify the functional groups in
amoxicillin.
NH2
H
N
S
O
HO
N
O
O
HO
Ans:
aromatic
amine
NH2
amide
sulfide
H
N
phenol
S
HO
O
N
O
amide
O
HO
carboxylic acid
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Hard
63. Viracept, used in the treatment of HIV, has the following structure. Identify the
functional groups in Viracept.
H
S
O
N
O
HO
N
N
H
OH
aromatic
Ans:
H
sulfide
S
phenol
O
N
O
HO
N
amide H
N
amide
OH
amine
aromatic
alcohol
Topic: Carbon Atoms with Formal Charges
Section: 2.4
Difficulty Level: Easy
64. What is the formal charge on the oxygen atom in the following compound?
O
A) +1
B) +2
C) -1
D) -2
E) 0
Ans: A
Topic: Carbon Atoms with Formal Charges
Section: 2.4
Difficulty Level: Easy
65. What is the formal charge on the nitrogen atom in the following compound?
N
A) -1
B) -2
C) +1
D) +2
E) 0
Ans: C
Topic: Carbon Atoms with Formal Charges
Section: 2.4
Difficulty Level: Easy
66. What is the formal charge on the nitrogen atom in the following compound?
N
A) +1
B) +2
C) -1
D) -2
E) 0
Ans: A
Topic: Carbon Atoms with Formal Charges
Section: 2.4
Difficulty Level: Easy
67. What is the formal charge on the indicated oxygen atom in the following compound?
O
O
A) +1
B) +2
C) -1
D) -2
E) 0
Ans: E
Topic: Carbon Atoms with Formal Charges
Section: 2.4
Difficulty Level: Easy
68. What is the formal charge on the nitrogen atom in the following compound?
N
A) +1
B) +2
C) -1
D) -2
E) 0
Ans: E
Topic: Carbon Atoms with Formal Charges
Section: 2.4
Difficulty Level: Medium
69. Which of the following compounds have +1 as a formal charge on an oxygen atom?
O
O
O
N
N
O
I
O
II
A) I
B) II
C) III
D) IV
E) Both I & IV
Ans: B
Topic: Carbon Atoms with Formal Charges
Section: 2.4
Difficulty Level: Medium
III
IV
70. Which of the following compounds have +1 as a formal charge on the nitrogen atom?
O
O
N
N
I
N
II
III
N
IV
A) I
B) II
C) III
D) IV
E) Both I & II
Ans: D
Topic: Carbon Atoms with Formal Charges
Section: 2.4
Difficulty Level: Medium
71. Determine the formal charges on each atom except hydrogen.
H
H
C
S
C
N
H
H
Ans:
H
0
C
+1
0
-1
S
C
N
H
Topic: Carbon Atoms with Formal Charges
Section: 2.4
Difficulty Level: Hard
72. Diazomethane has the molecular formula CH2N2. Draw the preferred Lewis structure for
diazomethane and assign formal charges to all atoms, if any.
-1
+1
0
Ans:
H
C
N
N
H
Topic: Carbon Atoms with Formal Charges
Section: 2.4
Difficulty Level: Easy
73. How many hydrogen atoms are connected to the indicated carbon atom?
A) one
B) two
C) three
D) four
E) none
Ans: A
Topic: Carbon Atoms with Formal Charges
Section: 2.4
Difficulty Level: Easy
74. How many hydrogen atoms are connected to the indicated carbon atom?
A) one
B) two
C) three
D) four
E) none
Ans: E
Topic: Carbon Atoms with Formal Charges
Section: 2.4
Difficulty Level: Easy
75. How many hydrogen atoms are connected to the indicated carbon atom?
A) one
B) two
C) three
D) four
E) none
Ans: A
Topic: Carbon Atoms with Formal Charges
Section: 2.4
Difficulty Level: Easy
76. How many hydrogen atoms are connected to the indicated carbon atom?
A) one
B) two
C) three
D) four
E) none
Ans: A
Topic: Carbon Atoms with Formal Charges
Section: 2.4
Difficulty Level: Easy
77. How many hydrogen atoms are connected to the indicated carbon atom?
A) one
B) two
C) three
D) four
E) none
Ans: E
Topic: Carbon Atoms with Formal Charges
Section: 2.4
Difficulty Level: Easy
78. How many hydrogen atoms are connected to the indicated carbon atom?
A) one
B) two
C) three
D) four
E) none
Ans: A
Topic: Carbon Atoms with Formal Charges
Section: 2.4
Difficulty Level: Medium
79. Draw Lewis structure for the following compound.
O
Ans:
O
H
H
C
H
H
C
C
C
C
C
H
H
H
H
H
H
Topic: Identifying lone pairs
Section: 2.5
Difficulty Level: Easy
80. How many lone pairs of electrons are on the oxygen atom?
O
A) one
B) two
C) three
D) four
E) none
Ans: C
Topic: Identifying lone pairs
Section: 2.5
Difficulty Level: Easy
81. How many lone pairs of electrons are on the nitrogen atom?
N
A) one
B) two
C) three
D) four
E) none
Ans: B
Topic: Identifying lone pairs
Section: 2.5
Difficulty Level: Easy
82. How many lone pairs of electrons are on the oxygen atom?
O
N
A) one
B) two
C) three
D) four
E) none
Ans: B
Topic: Identifying lone pairs
Section: 2.5
Difficulty Level: Easy
83. How many lone pairs of electrons are on the nitrogen atom?
O
N
A) one
B) two
C) three
D) four
E) none
Ans: A
Topic: Identifying lone pairs
Section: 2.5
Difficulty Level: Easy
84. How many lone pairs of electrons are on the nitrogen atom?
N
A) one
B) two
C) three
D) four
E) none
Ans: E
Topic: Identifying lone pairs
Section: 2.5
Difficulty Level: Easy
85. How many lone pairs of electrons are on the indicated oxygen atom?
O
O
A) one
B) two
C) three
D) four
E) none
Ans: B
Topic: Identifying lone pairs
Section: 2.5
Difficulty Level: Easy
86. How many lone pairs of electrons are on the indicated oxygen atom?
O
O
A) one
B) two
C) three
D) four
E) none
Ans: A
Topic: Identifying lone pairs
Section: 2.5
Difficulty Level: Medium
87. How many total lone pairs of electrons are on both oxygen atoms in the following
compound?
H2O
O
A) one
B) two
C) three
D) four
E) none
Ans: C
Topic: Identifying lone pairs
Section: 2.5
Difficulty Level: Medium
88. Draw all lone pairs of electrons for the following compound.
O
H3 N
O
OH
Ans:
O
H3 N
O
OH
Topic: Identifying lone pairs
Section: 2.5
Difficulty Level: Medium
89. Draw all lone pairs of electrons for the following compound.
OH
C
N
O
Ans:
OH
C
N
O
Topic: Three-Dimensional Bond-Line Structures
Section: 2.6
Difficulty Level: Easy
90. The indicated bond in the following compound is_____ of the paper.
A) in the plane
B) out of the plane
C) behind the plane
D) None of these
Ans: B
Topic: Three-Dimensional Bond-Line Structures
Section: 2.6
Difficulty Level: Easy
91. The indicated bond in the following compound is_____ of the paper.
OH
OH
OH
A) in the plane
B) out of the plane
C) behind the plane
D) None of these
Ans: C
Topic: Three-Dimensional Bond-Line Structures
Section: 2.6
Difficulty Level: Easy
92. The indicated bond in the following compound is_____ of the paper.
O
A) in the plane
B) out of the plane
C) behind the plane
D) None of these
Ans: C
Topic: Three-Dimensional Bond-Line Structures
Section: 2.6
Difficulty Level: Easy
93. Which of the following is a Fischer projection?
O
H
C
OH
OH
H
OH
H
OH
H
OH
H
OH
H
OH
OH
OH
H
I
II
CH2OH
A) I
B) II
C) III
D) IV
E) Both III & IV
Ans: B
Topic: Three-Dimensional Bond-Line Structures
Section: 2.6
Difficulty Level: Easy
III
IV
94. Which of the following is a Haworth projection?
O
H
C
OH
OH
H
OH
H
OH
H
OH
H
OH
H
OH
OH
OH
H
I
II
III
IV
CH2OH
A) I
B) II
C) III
D) IV
E) Both III & IV
Ans: C
Topic: Three-Dimensional Bond-Line Structures
Section: 2.6
Difficulty Level: Medium
95. For the following compound label the bonds that are out of the plane and behind the
plane of the paper.
HO
O
O
OH
HO
OH
HO
Ans:
O
out of the plane
O
OH
HO
OH
behind the plane
Topic: Introduction to Resonance
Section: 2.7
Difficulty Level: Easy
96. Which of the following pairs are resonance structures of each other?
I.
II.
O
III.
O
IV.
N
N
A) I
B) II
C) III
D) IV
E) None of these
Ans: D
Topic: Introduction to Resonance
Section: 2.7
Difficulty Level: Easy
97. Which of the following pairs are resonance structures of each other?
I.
II.
O
III.
O
IV.
N
A) I
B) II
C) III
D) IV
E) None of these
Ans: C
Topic: Introduction to Resonance
Section: 2.7
Difficulty Level: Easy
N
98. Spreading of positive or negative charge over two or more atoms in a compound is
called_______.
A) isomerism
B) delocalization
C) stereoisomerism
D) localization
E) None of these
Ans: B
Topic: Introduction to Resonance
Section: 2.7
Difficulty Level: Easy
99. Delocalization of charge over two or more atoms _______ a molecule.
A) destabilizes
B) delocalizes
C) localizes
D) stabilizes
E) None of these
Ans: D
Topic: Introduction to Resonance
Section: 2.7
Difficulty Level: Medium
100. Resonance structures have _______ connectivity of atoms and _______ distribution of
electrons.
A) different, same
B) same, same
C) different, different
D) same, different
E) None of these
Ans: D
Topic: Introduction to Resonance
Section: 2.7
Difficulty Level: Medium
101. What is a resonance hybrid?
Ans: A molecule that can be represented by drawing two or more resonance structures
is viewed as resonance hybrid.
Topic: Curved Arrows
Section: 2.8
Difficulty Level: Easy
102. Which of the following violates the rules for curved arrows?
O
OH
O
O
II
I
III
A) I
B) II
C) III
D) IV
E) None of these
Ans: A
Topic: Curved Arrows
Section: 2.8
Difficulty Level: Easy
103. Which of the following violates the rules for curved arrows?
N
H
H
H
H
H
H
N
C
O
C
I
II
III
IV
A) I
B) II & IV
C) I & III
D) III & IV
E) None of these
Ans: C
Topic: Curved Arrows
Section: 2.8
Difficulty Level: Easy
IV
104. Which of the following violates the rules for curved arrows?
N
II
I
O
O
III
IV
A) I & II
B) III & IV
C) I, II & III
D) II, III & IV
E) All of these
Ans: C
Topic: Curved Arrows
Section: 2.8
Difficulty Level: Medium
105. Provide the curved arrow(s) to draw a resonance structure for the following compound.
O
Ans:
O
Topic: Curved Arrows
Section: 2.8
Difficulty Level: Medium
106. Provide the curved arrow(s) to draw a resonance structure for the following compound.
Ans:
Topic: Curved Arrows
Section: 2.8
Difficulty Level: Hard
107. Provide the curved arrow(s) to draw a resonance structure for the following compound.
O
O
Ans:
O
O
Topic: Curved Arrows
Section: 2.8
Difficulty Level: Hard
108. Explain using words as well as structural drawings, if the single curved arrow shown is
sufficient to draw the resonance structure.
O
O
Ans: The single arrow shown will violate the octet rule. Drawing another curved arrow
will remove the violation.
O
O
Topic: Formal Charges in Resonance Structures
Section: 2.9
Difficulty Level: Easy
109. Which of the following is a correct resonance structure for compound A?
N
NH
NH
NH
N
A
I
II
III
IV
A) I
B) II
C) III
D) IV
E) none of these
Ans: D
Topic: Formal Charges in Resonance Structures
Section: 2.9
Difficulty Level: Easy
110. Which of the following is a correct resonance structure for compound A?
A
I
II
III
IV
A) I
B) II
C) III
D) IV
E) None of these
Ans: C
Topic: Formal Charges in Resonance Structures
Section: 2.9
Difficulty Level: Medium
111. Which of the following is/are correct resonance structure(s) for compound A?
O
A
O
I
II
A) I
B) II & III
C) III & IV
D) I & III
E) I & IV
Ans: B
Topic: Formal Charges in Resonance Structures
O
O
O
III
IV
Section: 2.9
Difficulty Level: Medium
112. Which of the following is/are correct resonance structure(s) for compound A
N
N
N
N
A
III
II
I
N
IV
A) I & II
B) II & III
C) III & IV
D) I & III
E) I & IV
Ans: C
Topic: Formal Charges in Resonance Structures
Section: 2.9
Difficulty Level: Medium
113. Which of the following is/are correct resonance structure(s) for compound A?
O
A
O
I
O
II
O
III
A) I & II
B) II & III
C) III & IV
D) I, II & III
E) I & IV
Ans: D
Topic: Formal Charges in Resonance Structures
Section: 2.9
Difficulty Level: Easy
114. Draw the resonance structure indicated by the curved arrows.
O
Ans:
O
Topic: Formal Charges in Resonance Structures
Section: 2.9
O
IV
Difficulty Level: Easy
115. Draw the resonance structure indicated by the curved arrows.
Ans:
Topic: Formal Charges in Resonance Structures
Section: 2.9
Difficulty Level: Medium
116. Draw the resonance structure indicated by the curved arrows.
NH2
Ans:
NH2
Topic: Formal Charges in Resonance Structures
Section: 2.9
Difficulty Level: Medium
117. Draw the resonance structure indicated by the curved arrows.
OH
Ans:
OH
Topic: Formal Charges in Resonance Structures
Section: 2.9
Difficulty Level: Medium
118. Draw the curved arrow(s) for converting the first resonance structure into the second
resonance structure.
O
O
Ans:
O
O
Topic: Formal Charges in Resonance Structures
Section: 2.9
Difficulty Level: Medium
119. Draw the curved arrow(s) for converting the first resonance structure into the second
resonance structure.
Ans:
Topic: Formal Charges in Resonance Structures
Section: 2.9
Difficulty Level: Hard
120. Draw the curved arrow(s) for converting the first resonance structure into the second
resonance structure.
O
O
O
O
Ans:
O
O
O
O
Topic: Formal Charges in Resonance Structures
Section: 2.9
Difficulty Level: Hard
121. Draw the curved arrow(s) for converting the first resonance structure into the second
resonance structure.
O
O
Ans:
O
Topic: Formal Charges in Resonance Structures
Section: 2.9
Difficulty Level: Hard
O
122. Explain using words as well as structural drawings, if the single curved arrow shown is
sufficient for the following resonance structures?
O
O
O
O
Ans: The single arrow shown will violate the octet rule. Drawing another curved arrow
will remove the violation.
O
O
O
O
Topic: Pattern Recognition
Section: 2.10
Difficulty Level: Easy
123. Which of the following is a correct resonance structure for compound A
O
O
O
O
A
A) I
B) II
C) III
D) IV
E) None of these
Ans: A
Topic: Pattern Recognition
Section: 2.10
Difficulty Level: Easy
OH
O
O
I
O
II
O
III
IV
124. Which of the following is a correct resonance structure for compound A?
Cl
A
Cl
Cl
II
I
Cl
Cl
III
IV
A) I
B) II
C) III
D) IV
E) None of these
Ans: C
Topic: Pattern Recognition
Section: 2.10
Difficulty Level: Easy
125. Which of the following is a correct resonance structure for compound A?
N
N
N
N
N
A
I
II
III
IV
A) I
B) II
C) III
D) IV
E) None of these
Ans: B
Topic: Pattern Recognition
Section: 2.10
Difficulty Level: Easy
126. Which of the following is a correct resonance structure for compound A?
A
A) I
B) II
C) III
D) IV
E) None of these
Ans: A
Topic: Pattern Recognition
I
II
III
IV
Section: 2.10
Difficulty Level: Medium
127. Draw resonance structures for the following compound.
O
Ans:
O
O
O
O
Topic: Pattern Recognition
Section: 2.10
Difficulty Level: Hard
128. Draw two additional resonance structures for the following compound.
Ans:
Topic: Pattern Recognition
Section: 2.10
Difficulty Level: Hard
129. Draw two additional resonance structures for the following compound.
N
Ans:
N
O
N
N
Topic: Pattern Recognition
Section: 2.10
Difficulty Level: Hard
O
N
N
O
N
N
O
130. Draw two additional resonance structures for the following compound.
N
Ans:
C
N
N
N
Topic: Assessing Importance
Section: 2.11
Difficulty Level: Easy
131. Which of the following is/are the most significant resonance structure(s)?
H
N
H
N
H
N
I
III
II
A) I
B) II
C) III
D) II & III
E) all of these
Ans: C
Topic: Assessing Importance
Section: 2.11
Difficulty Level: Easy
132. Which of the following is/are the most significant resonance structure(s)?
O
O
I
A) I
B) II
C) III
D) I & II
E) all of these
Ans: B
Topic: Assessing Importance
Section: 2.11
Difficulty Level: Easy
II
O
III
133. Which of the following is/are the most significant resonance structure(s)?
C
N
I
N
II
N
III
A) I
B) II
C) III
D) I & II
E) all of these
Ans: C
Topic: Assessing Importance
Section: 2.11
Difficulty Level: Medium
134. Which of the following is/are the most significant resonance structure(s)?
O
O
I
O
II
O
III
IV
A) I
B) II
C) III
D) I & II
E) I & IV
Ans: C
Topic: Assessing Importance
Section: 2.11
Difficulty Level: Medium
135. Which of the following is the most significant resonance structure?
H2C
N
N
I
A) I
B) II
C) III
D) IV
E) None of these
Ans: C
Topic: Assessing Importance
Section: 2.11
Difficulty Level: Medium
H2C
N
II
N
H2C
N
III
N
H2C
N
IV
N
136. Which of the following is/are the most significant resonance structure(s)?
N
N
I
II
N
III
A) I
B) II
C) III
D) I & III
E) all of these
Ans: B
Topic: Assessing Importance
Section: 2.11
Difficulty Level: Hard
137. Draw significant resonance structures for the following compound. Which of this is/are
most significant resonance structure(s)? Explain why.
H
H
C
C
N
O
H
H
Ans:
H
H
C
C
H
I
N
O
H
C
H
H
C
N
O
H
C
C
O
III
H
II
N
Resonance structure III is most significant, because the more electronegative
oxygen atom carries a negative formal charge.
Topic: Assessing Importance
Section: 2.11
Difficulty Level: Hard
138. Draw significant resonance structures for the following compound. Which of this is/are
most significant resonance structure(s)? Explain why.
O
Ans:
O
I
O
II
O
III
O
IV
Resonance structure III is most significant, because all atoms have octet of
electrons.
Topic: Assessing Importance
Section: 2.11
Difficulty Level: Hard
139. Draw significant resonance structures for the following compound. Which of this is/are
most significant resonance structure(s)? Explain why.
Ans:
Resonance structure I is most significant, because the more electronegative
oxygen atom carries a negative formal charge.
Topic: Assessing Importance
Section: 2.11
Difficulty Level: Easy
140. What is the relationship between the following compounds?
H
O
N
O
H
O
N
O
A) Constitutional isomers
B) Resonance structures
C) conformers
D) Identical compounds
Ans: B
Topic: Assessing Importance
Section: 2.11
Difficulty Level: Easy
141. What is the relationship between the following compounds?
O
A) Constitutional isomers
B) Resonance structures
C) conformers
D) Identical compounds
E) Different compounds
Ans: A
Topic: Assessing Importance
Section: 2.11
Difficulty Level: Easy
O
142. What is the relationship between the following compounds?
O
O
A) Constitutional isomers
B) Resonance structures
C) conformers
D) Identical compounds
E) Different compounds
Ans: B
Topic: Assessing Importance
Section: 2.11
Difficulty Level: Easy
143. What is the relationship between the following compounds?
A) Constitutional isomers
B) Resonance structures
C) conformers
D) Identical compounds
E) Different compounds
Ans: B
Topic: Delocalized and Localized Lone Pairs
Section: 2.12
Difficulty Level: Easy
144. The lone pair on nitrogen in the following compound is _______.
N
A) localized
B) delocalized
Ans: A
Topic: Delocalized and Localized Lone Pairs
Section: 2.12
Difficulty Level: Easy
145. The lone pair on oxygen in the following compound is _______.
O
A) localized
B) delocalized
Ans: B
Topic: Delocalized and Localized Lone Pairs
Section: 2.12
Difficulty Level: Easy
146. The lone pair on nitrogen in the following compound is _______.
O
N
A) localized
B) delocalized
Ans: A
Topic: Delocalized and Localized Lone Pairs
Section: 2.12
Difficulty Level: Easy
147. The lone pairs on oxygen in the following compound are _______.
O
N
A) both localized
B) both delocalized
C) one localized
D) one delocalized
E) Both C & D
Ans: E
Topic: Delocalized and Localized Lone Pairs
Section: 2.12
Difficulty Level: Easy
148. The lone pair on nitrogen in the following compound is _______.
N
N
N
A) localized
B) delocalized
Ans: A
Topic: Delocalized and Localized Lone Pairs
Section: 2.12
Difficulty Level: Medium
149. For the following compound identify the lone pairs and indicate if each lone pair is
localized or delocalized.
N
H2N
O
localized
Ans:
N
delocalized
H2N
O
localized
delocalized
Topic: Delocalized and Localized Lone Pairs
Section: 2.12
Difficulty Level: Medium
150. For the following compound identify the lone pairs and indicate if each lone pair is
localized or delocalized.
O
N
O
Ans:
localized
O
delocalized
N
O
localized
Topic: Delocalized and Localized Lone Pairs
Section: 2.12
Difficulty Level: Medium
151. For the following compound identify the lone pairs and indicate if each lone pair is
localized or delocalized.
OH
O
H
N
Ans: delocalized
localized
OH
O
H
N
delocalized
localized
Topic: Delocalized and Localized Lone Pairs
Section: 2.12
Difficulty Level: Hard
152. For the following compound what is the hybridization state and molecular geometry at
each oxygen and nitrogen atom
OH
O
H
N
sp2, bent
Ans: sp2, bent
OH
O
H
N
Topic: Delocalized and Localized Lone Pairs
Section: 2.12
Difficulty Level: Hard
sp2, trigonal planar
153. Caffeine has the following structure. What is the hybridization state and molecular
geometry at each nitrogen atom in Caffeine?
O
N
N
O
N
N
Ans:
O
sp2, trigonal planar
2
sp , trigonal planar
N
N
O
N
N
sp2, bent
sp2, trigonal planar
Topic: Delocalized and Localized Lone Pairs
Section: 2.12
Difficulty Level: Hard
154. 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?
O
O
N
N
O
HO
H
O
Ans:
sp2, bent
sp2, trigonal planar
O
O
N
sp2, bent
N
O
HO
O
H
sp3, trigonal pyramidal
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