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2. Credit for the first synthesis of an organic compound from an inorganic precursor is
generally ascribed to:
A) Berzelius
B) Arrhenius
C) Kekulé
D) Wöhler
E) Lewis
Ans: D
3. What was long thought to be the difference between inorganic and organic compounds?
A) The number of atoms
B) The synthesis of organic compounds required a vital force
C) The molecular weight
D) Inorganic compounds exhibited a strong nuclear force
E) Inorganic compounds were composed exclusively of transition metals
Ans: B
H
A) They are isotopes
B) They are constitutional isomers
C) They are the same structure
D) They are composed of different elements
E) There is no relationship
Ans: B
H C C O C H H C C C O H
H H H H H H
A) Resonance isomers
B) Constitutional isomers
C) Empirical isomers
D) There is no relationship
Ans: B
C C H C C C C C C
H C C H C H Br C H Br C H
H H H H Cl IV Cl
II III
I
A) I & II
B) III & IV
C) I, II & III
D) II, III & IV
E) All of these
Ans: E
H C C Cl Cl C C Cl H C C Cl H C C Cl
H Cl H Cl H H H Cl
I II III IV
A) I & II
B) III & IV
C) II & III
D) I & IV
E) All of these
Ans: D
10. Which of the following compounds are constitutional isomers of each other?
H
H
C H
H O
H H H H H H O H
N H C C
C
H C N C O C C H H H C C C N C H
O C N
H C H H
H H H H C H H H H C
H H
H
I II H III IV H H
A) I & II
B) III & IV
C) I, II & III
D) I & IV
E) All of these
Ans: C
11. Draw three constitutional isomers that have molecular formula C4H8BrCl
Ans: H H Br H H Cl Br H H H Br H
H C C C C Cl H C C C C H H C C C C H
H H H H H H H H H H Cl H
12. Draw three constitutional isomers that have molecular formula C4H8O.
H H H O H H
Ans: H H
H C C C C O H H C C C C H H C C C O C H
H H H H H H H H H H H
Cl C O Cl Cl C Cl Cl O Cl Cl O Cl Cl C Cl
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: B
H C C O O H C H C O H H C O O C H
H H H
I II III
H O H
H C C O H H C C O O H
H H
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: D
19. Which of the following compounds has two lone pairs on the central atom?
A) CO2
B) SCl2
C) NF3
D) CS2
E) SO3
Ans: B
H C O H
H H
A) 2-
B) 1-
C) 2+
D) 1+
E) 0
Ans: D
H C H
H C N
H H
A) 2-
B) 1-
C) 2+
D) 1+
E) 0
Ans: D
H C H
C C
H H H
H
A) 0
B) 1+
C) 2+
D) 1-
E) 2-
Ans: B
24. Which of the following structures have zero formal charge on carbon atom?
H H H H
H C H C H C H C
H H H
I II III IV
A) I & III
B) II & III
C) III & IV
D) I & IV
E) II & IV
Ans: C
25. Which of the following structures have 1- formal charge on sulfur atom?
H H H H O
S
H C S H C S C H O O H C S H H O S O H
H H H H O
III IV V
I II
A) I
B) II
C) III
D) IV
E) V
Ans: A
H H H H O
III IV V
I II
A) I
B) II
C) III
D) IV
E) V
Ans: C
27. What are the formal charges on boron and fluorine in the following structure?
F H
F B N H
F H
A) B = 1+, N = 1+
B) B = 1+, N = 1-
C) B = 1-, N = 1-
D) B = 1-, N = 1+
E) B = 1-, N = 0
Ans: D
28. What are the formal charges on boron and oxygen in the following structure?
H H
F C H
F B O
F C H
H H
A) B = 1-, O = 1-
B) B = 1-, O = 1+
C) B = 1+, O = 1+
D) B = 1+, O = 1-
E) B = 1-, O = 0
Ans: B
29. Which of the following structures have 1+ formal charge on the central atom?
H H H H
.. .. .. ..
H : Be : H H:B:H H:N:H H:N:H H:O:H
.. .. .. ..
H H
I II III IV V
A) I
B) II
C) III
D) III & V
E) IV & V
Ans: E
30. Which of the following structures have formal charge on at least one atom?
H
H N F H O O H H C F H O B O H
I II III H IV O
H
A) I
B) II
C) III
D) IV
E) None of these
Ans: A
H C N C H H C N H H C N H H C N C H H O N H
H H H H H H H H H H
V
I II III IV
A) I
B) II
C) III
D) IV
E) V
Ans: B
32. The bonding pattern of oxygen with a formal charge of –1 could be described as:
A) One lone pair of electrons and three single bonds
B) Two lone pairs of electrons and two single bonds
C) Three lone pairs of electrons, and one single bond
D) One lone pair of electrons, one single, and one double bond
E) Zero lone pairs, and two single and one double bond
Ans: C
33. In ammonium ion, nitrogen has a valence of 4, and zero nonbonding electrons. What is
the correct formal charge of nitrogen with 4 covalent bonds?
A) 2-
B) 2+
C) 1-
D) 1+
E) 0
Ans: D
O O O O O
N
H N H O H N
O O O N O O O
H
I II III IV
A) I
B) II
C) III
D) IV
E) None of these
Ans: D
35. What is the correct Lewis structure for hydrocyanic acid (HCN) including the formal
charges, if any?
H C N H C N H C N H C N H C N
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: B
36. What is the correct Lewis structure for SCN— including the formal charges, if any?
A) I
B) II
C) III
D) IV
E) V
Ans: A
37. What is the correct Lewis structure for N2O including the formal charges, if any?
N N O N N O N N O N N O N N O
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: B
38. What is the correct Lewis structure for hydrazoic acid (HN3) including the formal
charges, if any?
H N N N H N N N H N N N H N N N H N N N
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: A
39. Draw Lewis structure for NH2CN including formal charges, if any?
Ans:
H N C N
41. Draw Lewis structure for ozone (O3,) including formal charges, if any?
Ans:
O O O
47. What is the correct order of increasing electronegativity for Rb, F and O?
A) Rb < F < O
B) Rb < O < F
C) O < F < Rb
D) F < Rb < O
E) None of these
Ans: B
Topic: Induction and Polar Covalent bond
Section: 1.5
Difficulty Level: Medium
48. Which of the following series has the correct order of elements in increasing
electronegativity?
A) C < N < B < Br
B) P < N < As < F
C) Li < B < N < F
D) Cl < Cs < C < Co
E) Be < B < Ba < Br
Ans: C
52. The bond between carbon and hydrogen is best described as___________.
A) Nonpolar covalent
B) Polar covalent
C) Ionic
D) Coordinate covalent
E) None of these
Ans: A
53. Which of the following is the correct depiction of induction for a C—F bond?
C F C F C F C F
I II III IV
A) I
B) II
C) III
D) IV
E) None of these
Ans: A
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: C
55. Which of the following is the correct representation of partial charges at the indicated
atoms?
II
O
III
I
Cl C H
C C
H H H
H
H C N O
Br
A) N
B) O
C) Br
D) H
E) C
Ans: E
57. Which of the following statements best describes the C—Cl bond in the following
compound?
H H
Cl C H
C C
H H H
H
A) nonpolar; no dipole
B) polar; + at carbon and – at chlorine
C) polar; – at carbon and + at chlorine
D) ionic
E) None of these
Ans: B
58. Which of the following compounds have both polar covalent and ionic bonds?
A) NH4Br
B) H2O2
C) HCN
D) H2S
E) None of these
Ans: A
Cl C H
C C
H H H
H
O
Ans:
Cl C H
C C
H H H
H
60. For the following compound identify the polar covalent bonds and indicate the direction
of dipole moment using + and -.
O
Cl C H
C N
H H H
Ans:
61. For NaSCH3, identify each bond as polar covalent, nonpolar covalent or ionic.
Ans: polar covalent
H
Na S C H nonpolar covalent
H
ionic
C F
H C
H H
Ans: polar covalent
O
C + F
H C
H H polar covalent
nonpolar covalent
A) Quantum orbitals
B) Atomic orbitals
C) Antibonding orbitals
D) Bonding orbitals
E) Degenerate orbitals
Ans: E
64. What is the letter designation for the following atomic orbital?
A) s
B) p
C) d
D) f
E) g
Ans: B
65. What is the letter designation for the following atomic orbital?
A) s
B) p
C) d
D) f
E) g
Ans: C
67. Which of the following principle states that “Each orbital can accommodate a maximum
of two electrons with opposite spin”?
A) Aufbau principle
B) Pauli exclusion principle
C) Hund’s Rule
D) Heizenberg Uncertainty principle
E) Le Chatelier principle
Ans: B
69. Which of the following represents ground state electron configuration for phosphorous?
A) 1s2 2s2 2p6 3s1 3p4
B) 1s2 2s2 2p6 3s2 3p4
C) 1s2 2s2 2p6 3s2 3p3
D) 1s2 2s2 2p6 3s2 3p2
E) 1s2 2s2 2p6 3s2 3p5
Ans: C
70. The atomic number for nitrogen is 7. Which of the following represents ground state
electron configuration for nitrogen?
A) 1s2 2s1 2p4
B) 1s2 2p5
C) 2s2 2p5
D) 1s2 2s2 2p3
E) 1s2 2s2 3s3
Ans: D
71. Which element has the electron configuration 1s2 2s2 2p6 3s2 3p5?
A) oxygen
B) fluorine
C) sulfur
D) chlorine
E) bromine
Ans: D
Topic: Atomic Orbitals
Section: 1.6
Difficulty Level: Easy
72. Which element has the electron configuration 1s2 2s2 2p6 3s2 3p3?
A) Cl
B) S
C) P
D) Al
E) N
Ans: C
1s 2s 2p
A) boron
B) carbon
C) silicon
D) nitrogen
E) fluorine
Ans: D
1s 2s 2p
A) boron
B) carbon
C) silicon
D) nitrogen
E) fluorine
Ans: E
1s 2s 2p
A) the Aufbau principle
B) the Pauli Exclusion principle
C) Hund’s Rule
D) Heisenberg’s Uncertainty principle
E) None of these
Ans: C
1s 2s 2p
A) the Aufbau principle
B) the Pauli Exclusion principle
C) Hund’s Rule
D) Heisenberg’s Uncertainty principle
E) None of these
Ans: A
1s 2s 2p
A) the Aufbau principle
B) the Pauli Exclusion principle
C) Hund’s Rule
D) Heisenberg’s Uncertainty principle
E) None of these
Ans: B
86. The difference between valence bond theory and molecular orbital (MO) theory is:
A) valence bond theory requires the linear combination of atomic orbitals
B) MO theory requires the linear combination of atomic orbitals
C) valence bond theory considers only individual atomic orbitals
D) Both A & B
E) Both B & C
Ans: E
87. How many molecular orbitals are formed, when the 1s orbitals of two hydrogen atoms
combine to form a hydrogen molecule?
A) 1
B) 2
C) 3
D) 4
E) 5
Ans: B
88. Which molecular orbitals are formed, when the 1s orbitals of two hydrogen atoms
combine to form a hydrogen molecule?
A) Two bonding molecular orbitals
B) Only one bonding molecular orbital
C) One bonding and one antibonding molecular orbital
D) Two antibonding molecular orbitals
E) Only one antibonding orbital
Ans: C
Topic: Molecular orbital Theory
Section: 1.8
Difficulty Level: Medium
89. How are electrons distributed in the molecular orbitals, when the 1s orbitals of two
hydrogen atoms combine to form a hydrogen molecule?
A) 2 electrons in the bonding molecular orbital
B) 1 electron in the bonding molecular orbital, 1 electron in the non–bonding molecular
orbital
C) 1 electron in the bonding molecular orbital, 1 electron in the antibonding molecular
orbital
D) 2 electrons in the antibonding molecular orbital
E) 2 electrons in the non–bonding molecular orbital
Ans: A
90. According to molecular orbital theory the highest energy molecular orbital that is
occupied with an electron is referred to as:
A) degenerate
B) antibonding
C) the LCAO
D) the LUMO
E) the HOMO
Ans: E
91. According to molecular orbital theory the lowest energy molecular orbital that is
unoccupied with an electron is referred to as:
A) degenerate
B) antibonding
C) the LCAO
D) the LUMO
E) the HOMO
Ans: D
93. Which of the following molecules could not exist, according to the molecular orbital
theory?
A) He2
B) H2+
C) Li2
D) He2+
E) N2
Ans: A
94. According to molecular orbital theory, the constructive interference of two atomic
orbitals results in_______.
Ans: bonding molecular orbital
95. According to molecular orbital theory, the destructive interference of two atomic
orbitals results in_______.
Ans: antibonding molecular orbital
97. Interaction of the following two atomic orbitals results in what kind of molecular
orbital, in the orientation shown?
+
98. Interaction of the following two atomic orbitals results in what kind of molecular
orbital, in the orientation shown?
+
H C O H
H
A) sp
B) sp2
C) sp3
D) sp3d
E) s2 p
Ans: C
100. What is the hybridization state of the nitrogen atom in the following compound?
H
H C N H
H H
A) sp
B) sp2
C) sp3
D) sp3d
E) s2 p
Ans: C
101. What is the hybridization state of the boron atom in the following compound?
F
B
F F
A) sp
B) sp2
C) sp3
D) sp3d
E) s2 p
Ans: B
H H
A) sp
B) sp2
C) sp3
D) sp3d
E) sp3d2
Ans: B
103. What is the hybridization state of the nitrogen atom in the following compound?
H
C N
H
C O H
H H
A) sp
B) sp2
C) sp3
D) sp4
E) s2 p
Ans: B
C N
H
C O H
H H
A) sp2
B) sp3
C) sp
D) s
E) p
Ans: A
105. Which of the following structures have carbon with sp2 hybridization state?
H H H
H C H C H C H H C
H H H
II III H IV
I
A) I & II
B) III & IV
C) I & III
D) II & IV
E) I & IV
Ans: E
H C C H
C C C
H H H H
H IV
I II III
A) I & II
B) III & IV
C) II & III
D) I & III
E) II & IV
Ans: D
107. What is the correct order of hybridization state for the numbered carbon atoms in the
following compound?
H H H H
H
C C C
C C C H
C
H H H H
III
I II
A) I = sp3, II = sp2, III = sp
B) I = sp2, II = sp, III = sp2
C) I = sp, II = sp2, III = sp3
D) I = sp, II = sp2, III = sp
E) I = sp2, II = sp3, III = sp2
Ans: C
C C C
H C C H
H H
A) 2
B) 3
C) 4
D) 5
E) 6
Ans: D
109. The C1—C2 bond in the following compound results from the overlap of which orbitals?
H O
H C 1 C H
C C 2 C
H H H H H
2
A) sp–sp
B) sp–sp3
C) sp2–sp2
D) sp2–sp3
E) sp3–sp2
Ans: E
H C C H
C C C
H H H H H
2
A) sp–sp
B) sp–sp3
C) sp2–sp2
D) sp2–sp3
E) sp3–sp2
Ans: C
111. The C—C bond in ethyne (H—CC—H), results from the overlap of which orbitals?
A) sp–sp
B) sp–sp3
C) sp2–sp2
D) sp–s
E) p–p
Ans: A
H C C H
C C C
H H H H H
A) one
B) two
C) three
D) four
E) five
Ans: B
H
A) two
B) three
C) four
D) five
E) six
Ans: E
H
A) 20
B) 22
C) 24
D) 25
E) 27
Ans: E
C N
H
C O H
H H
A) sp2–sp2
B) sp–sp
C) sp2–sp3
D) sp3–sp3
E) sp3–sp2
Ans: A
116. The bonds indicated by the arrow in the following compound results from the overlap of
which orbitals?
H
H C C C C C H
H H H
A) sp2–sp2
B) sp3–sp3
C) p–p
D) Both A & B
E) Both A & C
Ans: E
H C H
C C
H H H H
A) Csp2—Osp2
B) Csp3—Osp3
C) Csp—Osp
D) Cp—Op
E) Csp—Op
Ans: A
118. Which of the following best describes the orbitals involved in the formation of C=O
bond in acetone, shown below?
O
H C H
C C
H H H H
A) C sp 2 – O sp 2 and C sp 2 O sp 2
B) C sp 2 – O sp 2 and C p O p
C) C sp 3 – O sp 2 and C p O p
D) C p – O p and C sp 2 O sp 2
E) C sp – O sp and C p O p
Ans: B
Topic: Hybridized Atomic orbitals
Section: 1.9
Difficulty Level: Medium
119. The C—H bond in the methyl cation, CH3+, results from the overlap of which orbitals?
A) sp3–sp2
B) sp3–sp3
C) sp2–s
D) sp3–p
E) p–s
Ans: C
120. The lone pair of electrons in the methyl anion, CH3—, resides in which orbitals?
A) s2
B) p
C) sp
D) sp3
E) sp2
Ans: D
121. What is the hybridization state of the indicated atoms in the following compound?
H
O C N C H
H
IV
I II III
A) I – sp ; II – sp2 ; III – sp3 ; IV – sp2
B) I – sp2 ; II – sp ; III – sp2 ; IV – sp3
C) I – sp3 ; II – sp2 ; III – sp ; IV – sp2
D) I – sp2 ; II – sp3 ; III – sp2 ; IV – sp
E) I – sp2 ; II – sp2 ; III – sp2 ; IV – sp3
Ans: B
122. The carbon and oxygen atoms in carbon monoxide are connected by which type of
bond(s)?
A) A sigma () bond
B) Two sigma () bonds
C) A pi () bond
D) Two pi () bonds
E) Both A and D
Ans: E
H C N H
H H
A) σ bond; sp2 – s orbital overlap
B) σ bond; sp3 – s orbital overlap
C) π bond; sp3 – s orbital overlap
D) π bond; sp2 – p orbital overlap
E) π bond; p – p orbital overlap
Ans: B
H C C C C C H
H H H
I II III IV
A) I
B) II
C) III
D) IV
E) I & III have the same length
Ans: C
H C C H H C C H H C C C H H C C H
H H H H H H H
I II III IV
A) I
B) II
C) III
D) IV
E) All of these
Ans: D
126. Compare the bond length and strength for the following compounds.
H C C H H C C H
H H II
I
A) The shortest and strongest bond is found in compound I
B) The shortest and strongest bond is found in compound II
C) The shortest and weakest bond is found in compound I
D) The shortest and weakest bond is found in compound II
E) The bonds are of identical length and strength
Ans: B
H C C C C C C H
H H H H
I II III
A) I
B) II
C) III
D) I & III
E) All of these
Ans: C
128. Rank the indicated C—C bonds in increasing order of bond length.
H H
H C C C C C C H
H H H H
I II III
A) I<II<III
B) II<III<I
C) III<I<II
D) II<I<III
E) I<III<II
Ans: A
129. For the hydrogen halides, which is the correct sequence for a) the molecule with the
weakest bond, b) the molecule with the shortest bond, and c) the molecule with the most
polar bond?
A) HF HI HBr
B) HI HBr HCl
C) HBr HI HF
D) HI HF HF
E) HCl HBr HI
Ans: D
H C C C C C C C N C O H
H H H H H H H
II III IV
I
A) I>II>III>IV
B) II>III>IV>I
C) IV>III>II>I
D) III>IV>I>II
E) II>I>III>IV
Ans: B
131. The molecular geometry of carbon tetrachloride, CCl4, is best described as:
A) tetrahedral
B) trigonal planar
C) trigonal pyramidal
D) square planar
E) linear
Ans: A
132. Which of the following compounds have trigonal planar molecular geometry?
F B F H O H H C H F N F
F H H F
I II III IV
A) I
B) II
C) III
D) IV
E) I & IV
Ans: A
F B F H O H H C H F N F
F H F
I II III IV
A) I
B) II
C) III
D) IV
E) I & IV
Ans: D
F B F H O H H C H F N F
F H F
I II III IV
A) I
B) II
C) III
D) IV
E) I & IV
Ans: B
135. Which of the following compounds have trigonal planar molecular geometry?
H C H H O H F B F H O H H C H
H H F IV H
I II III V
A) I, II & III
B) II & III
C) III & V
D) V only
E) All of these
Ans: C
H C H H O H F B F H O H H N H
I H II H III F IV V H
A) I, II & III
B) I, II, IV & V
C) III & IV & V
D) IV & V
E) All of these
Ans: B
137. Which of the following compounds have trigonal planar electron geometry?
H C H O S O F B F H O H H N H
I H II III F IV V H
A) I, II & III
B) I, II, IV & V
C) III & IV & V
D) II &III
E) All of these
Ans: D
140. What is the molecular geometry at the nitrogen atom in the following compound?
H
C N
H
C O H
H H
A) trigonal planar
B) trigonal pyramidal
C) linear
D) tetrahedral
E) bent
Ans: E
C C H
H C C
H H H H
A) 600
B) 900
C) 109.50
D) 1200
E) 1800
Ans: D
143. What is the approximate bond angle around the indicated carbon atom?
H
H C C O
H
A) 600
B) 900
C) 109.50
D) 1200
E) 1800
Ans: E
144. What is the approximate bond angle around the nitrogen atom?
H N H
C C
C C
H C H
H
A) 900
B) 109.50
C) 1200
D) 1800
E) 1000
Ans: C
Topic: VSEPR Theory: Predicting Geometry
Section: 1.10
Difficulty Level: Medium
145. What is the approximate bond angle around sulfur atom in SOCl2?
A) 900
B) 109.50
C) 1050
D) 1200
E) 1800
Ans: B
146. What is the hybridization state and approximate bond angle around carbon atom in
HCN?
A) sp2, 1200
B) sp, 1800
C) sp3, 109.50
D) sp3, 1200
E) sp, 1200
Ans: B
147. What is the hybridization state and approximate bond angle around nitrogen in the
following compound?
H H H H
C C
H N H
H C
H H
A) sp2, bond angle greater than 109.5°
B) sp2, bond angle less than 109.5°
C) sp3, bond angle greater than 109.5°
D) sp3, bond angle less than 109.50
E) sp2, bond angle exactly 109.50
Ans: D
H H H H
2
A) sp , bond angle greater than 109.5°
B) sp2, bond angle less than 109.5°
C) sp3, bond angle greater than 109.5°
D) sp3, bond angle less than 109.50
E) sp2, bond angle exactly 109.50
Ans: D
149. What is the hybridization state and molecular geometry around sulfur atom in SOCl2?
A) sp2, tetrahedral
B) sp2, trigonal planar
C) sp3, tetrahedral
D) sp3, trigonal pyramidal
E) sp2, trigonal pyramidal
Ans: D
150. What is the hybridization state and molecular geometry around carbon atom in COCl2?
A) sp2, tetrahedral
B) sp2, trigonal planar
C) sp3, tetrahedral
D) sp3, trigonal pyramidal
E) sp2, trigonal pyramidal
Ans: B
152. What are the hybridization state, molecular geometry and approximate bond angle for
methyl anion, CH3—?
A) sp2, tetrahedral, 1090
B) sp2, trigonal planar, 1200
C) sp3, tetrahedral, 109.50
D) sp3, trigonal pyramidal, 109.50
E) sp2, trigonal pyramidal, 1800
Ans: D
153. Draw Lewis structure for SOCl2 and predict the hybridization state, molecular geometry
and approximate bond angle around the central atom.
Ans: O
Cl S Cl
154. Draw Lewis structure for COCl2 and predict the hybridization state, molecular geometry
and approximate bond angle around the central atom.
Ans: O
Cl C Cl
155. Following is the structure for Propranolol, and antihypertensive drug. What are the
hybridization state, molecular geometry and approximate bond angle at the indicated
nitrogen and oxygen atom in Propranolol?
H H
H H
H H H H H CH3
C C C
H O N CH3
H H H O H
H
156. What are the hybridization state, molecular geometry and approximate bond angle at
each nitrogen atom in the following compound?
O
H3C C H
O
C
H
CH3 N I
H C C
C C H
II H
N C
H C
H
H H
II H C O H
H
H C C N H
H C
C H H
C C IV
C H
C C
N
H C
III
H
H
Ans: C(I): sp2, trigonal planar, 1200
C(II): sp3, tetrahedral, 109.50
C(III): sp2, trigonal planar, 1200
N(IV): sp3, trigonal pyramidal, 109.50
158. Which of the following covalent bonds has the largest dipole moment?
A) C—C
B) C—H
C) C—O
D) N—H
E) H—F
Ans: E
162. Which of the following compounds does not have dipole moment?
A) HCl
B) NCl3
C) CO
D) BF3
E) All have dipole moment
Ans: D
C C C C C C C C
C C
H F F F F F F H
F H V
II III IV
I
A) I
B) II
C) III
D) IV
E) V
Ans: A
O C O N C O N C S C O
I II III IV
A) II
B) III
C) II & III
D) I, II & III
E) II, III & IV
Ans: E
C C C C C C
F H F F F F
I II III
A) I>II>III
B) II>III>I
C) I>III>II
D) III>II>I
E) II>I>III
Ans: D
166. Rank the following compounds in order of decreasing (highest to lowest) dipole
moment.
O O O
H H H H
H
C C C
O
C C H C C C C
H H H H
H C C H C C H H C C H
C O C C
H H H H
H
H H O H H
I II III
A) I>II>III
B) II>III>I
C) I>III>II
D) III>I>II
E) II>I>III
Ans: D
C C C C
F H F H
I II
Ans: Compound I has no dipole moment.
Compound II has dipole moment.
H Cl
C C
F H
II
168. Which of the following compounds have a dipole moment? Indicate the direction of
dipole moment.
Br Br
H C H H C H
C C C C
C C
H C H H C H
F Br
I II
Ans: Compound II has no dipole moment.
Compound I has a dipole moment.
Br Br
H C H H C H
C C C C
C C
H C H H C H
F Br
I II
F
The trigonal planar geometry of BF3 results in the cancellation of individual bond
dipoles, producing a net molecular dipole of zero.
170. Which of the intermolecular forces listed below is generally considered the strongest?
A) London dispersion forces
B) Fleeting dipole-dipole interactions
C) Dipole-dipole interactions
D) Hydrogen bonding
E) The Vital force
Ans: D
173. What is the strongest intermolecular force present in the following compound?
H H H H
H C C C C O H
H H H H
A) Ion-dipole interactions
B) London dispersion forces
C) Dipole-dipole interactions
D) Hydrogen bonding
E) Covalent bonding
Ans: D
174. What is the strongest intermolecular force present in the following compound?
H H H H
H C C C C S H
H H H H
A) Ion-dipole interactions
B) London dispersion forces
C) Dipole-dipole interactions
D) Hydrogen bonding
E) Covalent bonding
Ans: C
176. Which of the following compounds have the greatest fleeting dipole interactions
between like molecules?
H H
H H H H
H H C H H H H H H H C H H H H H H H
H C C C C H H C C C C C H H C C C H H C C C C C C H
H H H H H H H H H H C H H H H H H H
H H IV
I II III H
A) I
B) II
C) III
D) IV
E) I, III & IV
Ans: D
177. Which of the following compounds have the highest boiling point?
H H H H H H H H H H H H H H H H
H C C C C C H H C C C C O H H C C O C C H H C C C Cl
H H H H H H H H H H H H H H H H
I II III IV
A) I
B) II
C) III
D) IV
E) II & IV
Ans: B
H C C C C C H H C C C C O H H C C C C H H C C C Cl
H H H H H H H H H H H H H H H H
I II III IV
A) I
B) II
C) III
D) IV
E) II & IV
Ans: C
179. Which of the following compounds have the lowest boiling point?
A) CH3Cl
B) CH2Cl2
C) CH4
D) CHCl3
E) CCl4
Ans: C
180. Which of the following compounds have the lowest boiling point?
H H
H H H H
H H C H H H H H H H C H H H H H H H
H C C C C H H C C C C C H H C C C H H C C C C C C H
H H H H H H H H H H C H H H H H H H
H H IV
I II III H
A) I
B) II
C) III
D) IV
E) I & III
Ans: C
H H H H H H H H H H C H H H H H H H
H H IV
I II III H
A) III>I>IV>II
B) II>I>IV>III
C) III>I>II>IV
D) IV>II>I>III
E) I>III>II>IV
Ans: D
182. Rank the following compounds in decreasing (highest to lowest) order of boiling point?
H
H H
H H H H H H H H H H C H H H H H H
H C C C C C H H C C C C O H H C C C C H H C C C C N H
H H H H H H H H H H H H H H H H H H
I II IV
III
A) III>I>IV>II
B) II>IV>I>III
C) III>I>II>IV
D) IV>II>I>III
E) I>III>II>IV
Ans: B
H H H H H H H H H H H H H O H
H C C C C O H H C C O C C H H O C C C O H H C C C C H
H H H H H H H H H H H H H H H
I II III IV
A) III>I>IV>II
B) II>IV>III>II
C) III>I>II>IV
D) IV>II>I>III
E) I>III>II>IV
Ans: A
184. Which of the following compounds have a higher boiling point? Explain why.
H
H H
H H C H H H H H H
H C C C C H H C C C C C H
H H H H H H H H H
I II
Ans: Compound II has a higher boiling point than compound I. Compound II has larger
surface area that allows for stronger fleeting dipole-dipole interactions between
molecules.
185. Which of the following compounds have a higher boiling point? Explain why.
H H H H H H H H
H C C C C O H H C C O C C H
H H H H H H H H
I II
Ans: Compound I has a higher boiling point than compound II. Compound I has
hydrogen bonding interactions between molecules. Compound II has dipole-
dipole interactions that are weaker than hydrogen bonding interactions.
Topic: Solubility
Section: 1.13
Difficulty Level: Easy
186. Which of the following compounds is most soluble in water?
H H H H H H H H H H H H H H H H
H C C C C C H H C C C C O H H C C O C C H H C C C Cl
H H H H H H H H H H H H H H H H
I II III IV
A) I
B) II
C) III
D) IV
E) II & III
Ans: B
Topic: Solubility
Section: 1.13
Difficulty Level: Easy
H C C C C C H H C C C C O H H C C O C C H H C C C Cl
H H H H H H H H H H H H H H H H
I II III IV
A) I
B) II
C) III
D) IV
E) II & III
Ans: A
Topic: Solubility
Section: 1.13
Difficulty Level: Medium
188. For soap to remove and dissolve oil in water, what molecular features are needed?
A) One end of the molecule must be polar
B) The compound must contain oxygen atoms
C) One end of the molecule must be nonpolar
D) Both A & C
E) All A, B & C
Ans: D
Topic: Solubility
Section: 1.13
Difficulty Level: Medium
189. Amino acids are building blocks of proteins. Which statement best describes the
physical properties of the following amino acid?
O H
H O C C N H
H H
A) high melting points and low solubility in water
B) large dipole moments and no hydrogen bonding
C) high melting points and large dipole moments
D) low solubility in water and small dipole moments
E) small dipole moments and are hydrophobic
Ans: C
Topic: Solubility
Section: 1.13
Difficulty Level: Medium
190. Sugars, an example of which is shown below, tend to be very soluble in water. Explain
why.
H
OH
H
H C
HO
H
C C
H
C O
HO C C
OH
H
OH H
(The lone pairs of electrons on the oxygen atoms are not shown for clarity)
Ans: Favorable hydrogen bonding between the sugar and water readily occurs as both
contain O–H groups capable of hydrogen bonding.
Topic: Solubility
Section: 1.13
Difficulty Level: Medium