TEST BANK Introduction to Organic Chemistry William Brown and Thomas Poon 3rd Edition

CHAPTER 1. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1
CHAPTER 2. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 12
CHAPTER 3. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 24
CHAPTER 4. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 36
CHAPTER 5. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 48
CHAPTER 6. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 61
CHAPTER 7. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 75
CHAPTER 8. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 88
CHAPTER 9. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 100
CHAPTER 10. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 116
CHAPTER 11. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 130
CHAPTER 12. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 138
CHAPTER 13. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 148
CHAPTER 14. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 161
CHAPTER 15. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 176
CHAPTER 16. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 191
CHAPTER 17. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 207
CHAPTER 18. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 221
CHAPTER 19. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 235
CHAPTER 20. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 247
CHAPTER 21. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 258
CHAPTER 22. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 271
Chapter 1 Covalent Bonding and Shapes of Molecules
1
Multiple Choice
1. Which is the electronic configuration that describes Mg2+? (Sec. 1.2)
a) 1s2, 2s2
b) 1s2, 2s2, 2p6
c) 1s2, 2s2, 2p6, 3s2
d) 1s2, 2s2, 2p6, 3s2, 3p6
2. Which is the electronic configuration that describes C? (Sec. 1.2)
a) 1s2, 2s2, 2p5
b) 1s2, 2s2, 2p6, 3s2
c) 1s2, 2s2, 2p2
d) 1s2, 2s2, 2p6
3. Which ion is described by the electronic configuration 1s22s22p63s23p2? (Sec. 1.2)
a) Mg+
b) Al+
c) Si+
d) P+
4. Which atom is described by the electron configuration 1s22s22p63s23p7? (Sec. 1.2)
a) S
b) Se
c) Cl
d) Br
5. Which atom is described by the Lewis structure A ? (Sec. 1.2)
a) C
b) P
c) Se
d) I
6. Which atom is described by the Lewis structure A ? (Sec. 1.2)
a) C
b) P
c) Se
d) I
7. Which molecules contain both covalent and ionic bonds? (Sec. 1.3)
CH3OH Na2CO3 NH4Cl NaCl
I II III IV
a) I, II
b) II, IV
c) I, II, IV
d) II, III
Chapter 1 Covalent Bonding and Shapes of Molecules
2
8. Arrange the bonds in increasing order of ionic character (least first). (Sec. 1.3)
C-C Na-O C-N O-H C-O
I II III IV V
a) III, I, IV, II, V
b) V, III, I, II, IV
c) I, III, V, IV, II
d) I, III, II, IV, V
9. Which Lewis structure is correct? (Sec. 1.3)
C
H
H
H
OH C C
H
H
H
H H O O H C
O
.. .. .. .. H O O H
.. ..
.. ..
: :
a) b) c) d)
10. Which Lewis structures are correct? (Sec. 1.3)
a) I, II
b) II, IV
c) III, IV
d) I, III
11. Which molecules are polar? (Sec. 1.5)
a) I, IV
b) I, III
c) II, III, IV
d) III, IV, V
H O O H N N
H
H
H
H N
H
H
H
O C
H
H
H
Cl
I II III IV
I II III IV V
NH3 CO2 H2O CH4 Br2
Chapter 1 Covalent Bonding and Shapes of Molecules
3
12. Which molecules are polar? (Sec. 1.5)
a) III, IV, V
b) I, IV
c) II, III, V
d) I, III
13. Which functional groups have correct Lewis structures? (Sec. 1.3)
a) I, II
b) II, III
c) I, II, III
d) I, III
14. Which is the correct Lewis structure for acetic acid (CH3CO2H)? (Sec. 1.3)
15. Using the VSEPR model, predict which atoms have bond angles of about 120°. (Sec. 1.4)
a) II, IV
b) I, IV
c) II, III
d) I, III
C
O
H
H
C
H
O
H
C
H
H
H
C
H
O
O
C
H
H
H
O C
O
H H O C
O
C
H
H
H
a) b) c) d)
I II III IV V
CH3OH H3C CH3
C CH2Cl2
O
H H
H2C CH2
C
O
C O H C O O H
hydroxyl
I
carbonyl
II
carboxyl
III
I II III IV
C CH3OH CH2 CH2 NH4Cl
O
H3C H
Chapter 1 Covalent Bonding and Shapes of Molecules
4
16. According to VSEPR model, what is your prediction for the arrangement of electron pairs for CH3
-? (Sec. 1.4)
a) linear
b) tetrahedral
c) bent
d) trigonal
17. Using the VSEPR model, predict which species have bond angles of about 109°. (Sec. 1.4)
a) I, III, IV
b) II, III, V
c) I, IV
d) III, IV, V
18. What is the correct structure for the aldehyde which has the formula C4H8O? (Sec. 1.3)
19. Nitrogen has a negative formal charge in which of the following compounds? (Sec. 1.3)
a) NaNH2
b) N2
c) NH4Cl
d) HCN
20. What is the formal charge of oxygen in H3O+? (Sec. 1.3)
a) –1
b) 0
c) +1
d) +2
21. What is the formal charge of indicated carbon in,
NaC CH
(Sec. 1.3)
a) –2
b) –1
c) 0
d) +1
c) d)
a) b)
H2C CH CH2O CH3
CH3 CH2 CH2 CH
O
CH3 C
O
CH3 CH CH2 CH3
OH
CH CH2
NH3 CO2 H2O H3O+ O3
I II III IV V
Chapter 1 Covalent Bonding and Shapes of Molecules
5
22. The carbon has the correct orbital hybridization in which structures? (Sec. 1.7)
a) II, IV, V
b) II, III, IV
c) I, II, III
d) I, IV, V
23. What are the correct orbital hybridizations for carbon in the following species? (Sec. 1.7)
a) A and I, B and III
b) B and I, C and II
c) A and III, C and II
d) B and III, C and III
24. Which of the following are pairs of contributing resonance structures? (Sec. 1.6)
a) II, IV
b) I, II, III
c) III, IV
d) II, III, ,IV
CH3
CH4
CH3
A. I. sp
B. II. sp2
C. III. sp3
sp sp2 sp2 sp sp
I II III IV V
O C O HC N H2C CH2
H2C O
CH4
CH3
O
CH3
H2C O H2C O
H2C CH CH2
H2C CH CH2
N C O N C O
CH3
CH2
I OH
II
III
IV
Chapter 1 Covalent Bonding and Shapes of Molecules
6
25. Carbon has how many valence electrons? (Sec. 1.2)
a) 2
b) 4
c) 6
d) 8
26. Oxygen has how many valence electrons? (Sec. 1.2)
a) 4
b) 5
c) 6
d) 7
27. Nitrogen has how many valence electrons? (Sec. 1.2)
a) 4
b) 5
c) 6
d) 7
28. Which statement about orbitals is false? (Sec. 1.2)
a) Orbitals are regions of space where electrons are found.
b) Orbitals may contain up to two electrons.
c) Orbitals are filled in order of decreasing energy.
d) Orbitals of equivalent energy are half filled before adding two electrons to any one of them.
29. Which statement about resonance structures is false? (Sec. 1.6)
a) All contributing resonance structures must have the same number of valence electrons.
b) All contributing structures must obey the rules of covalent bonding.
c) The position of nuclei may change.
d) Third period atoms may have up to 12 electrons around them.
30. Which functional groups are named correctly? (Sec. 1.8)
a) III, IV, V
b) II, III, IV
c) I, III, V
d) I, III, IV
alcohol aldehyde ketone amine carboxylic acid
I II III IV V
C
O
H3C OH
N CH3
CH3
C H
O
H3C CH3
C CH3 OH
O
H3C H
Chapter 1 Covalent Bonding and Shapes of Molecules
7
31. Which of the following compounds contains a tertiary (3°) alcohol? (Sec. 1.8)
OH
H3C
H3C
CH3
C C
CH3
H3C
H3C
CH2
OH
OH
H3C
H3C
HC
H3C OH
HC
H3C
CH
CH3
I II III IV
a) I
b) II
c) III
d) IV
Chapter 1 Covalent Bonding and Shapes of Molecules
8
Fill in the Blanks
1. The spins of the electrons must be _______ in an orbital. (Sec. 1.2)
2. Outer shell electrons are called _________ electrons. (Sec. 1.2)
3. ______ is the number of valence electrons for S. (Sec. 1.2)
4. ______ is the number of valence electrons for Br. (Sec. 1.2)
5. The tendency of an element to react such that it achieves a noble gas configuration is called
the ______ ______. (Sec. 1.2)
6. The most polar bond in the following molecule is __________. (Sec. 1.3)
C C
OH
F
H H
H
C NH2
H
H
7. A __________ bond is characterized by the unequal sharing of electrons. (Sec. 1.3)
8. The following molecule contains the _________ and __________ functional groups. (Sec. 1.8)
O
OH
9. The following molecule contains the _________ and __________ functional groups. (Sec. 1.8)
NH2
O
OH
10. Functional groups undergo the same type of __________ in whatever compound they are found. (Sec. 1.8)
11. ______________ are the basis for compound nomenclature. (Sec. 1.8)
True-False
1. Each shell can hold two electrons. (Sec. 1.2)
2. Orbitals make up the majority of the mass of an atom. (Sec. 1.2)
3. The group 7A elements react by losing an electron to achieve a noble gas configuration. (Sec. 1.3)
4. The group 2A elements react by losing two electrons to achieve a noble gas configuration. (Sec. 1.3)
Chapter 1 Covalent Bonding and Shapes of Molecules
9
5. Carbon reacts by gaining 4 electrons to achieve a noble gas configuration. (Sec. 1.3)
6. An atom that gains electrons is called an anion. (Sec. 1.3)
7. Ionic bonds are characterized by the unequal sharing of electrons. (Sec. 1.3)
8. The following molecule is an example of a secondary amine. (Sec. 1.8)
NH2
H3C
H3C
HC
9. CH3CH2CH2CH2CH2OH is a polar molecule. (Sec. 1.5)
10. CH3ONa contains only polar covalent bonds. (Sec. 1.3)
Chapter 1 Covalent Bonding and Shapes of Molecules
10
Answers
Multiple Choice
1. b
2. c
3. d
4. c
5. c
6. a
7. d
8. c
9. d
10. c
11. b
12. c
13. d
14. d
15. d
16. b
17. a
18. c
19. a
20. c
21. b
22. a
23. c
24. c
25. b
26. c
27. b
28. c
29. c
30. a
31. b
Fill in the Blank
1. paired
2. valence
3. 6
4. 7
5. octet rule
6. C-F
7. polar covalent
8. ketone, alcohol
9. 1° amine, carboxylic acid
10. reactions
11. Functional groups
True-False
1. F
2. F
3. F
4. T
5. F
6. T
Chapter 1 Covalent Bonding and Shapes of Molecules
11
7. F
8. F
9. T
10. F
Chapter 2 Acids and Bases
12
Multiple Choice
1. Identify the Brønsted-Lowry acids in the following reactions. (Sec. 2.3)
a) I, III,VI, VII
b) II, VI
c) I, IV, V, VIII
d) II, III, V, VIII
2. Identify the conjugate bases in the following reactions. (Sec. 2.3)
a) II, III, VI
b) I, IV, V
c) I, III, V
d) II, IV, VI
V VI VII VIII
I II III IV
+
+
+
+
C2H5ONa H2 C2H5OH NaH
CH3OH HCl CH3OH2 Cl
V VI
III IV
I II
+ +
CH3OH + HCl CH3OH2 + Cl
C2H5OH NaH C2H5ONa H2 + +
CH3NH2 H3CCO2H CH3NH3 CH3CO2
Chapter 2 Acids and Bases
13
3. Identify the conjugate acids in the following reactions. (Sec. 2.3)
a) I, IV, VI
b) I, III, VI
c) II, IV, V
d) I, III, V
4. Which are acid-base reactions according to Brønsted-Lowry theory? (Sec. 2.3)
a) I, III
b) I, II, II, IV
c) I, II, III
d) I, III, IV
V VI
III IV
I II
+ +
CH3OH + HCl CH3OH2 + Cl
C2H5OH NaH C2H5ONa H2 + +
CH3NH2 CH3CO2H CH3NH3 CH3CO2
CH3
C
O
O
H3CNH3 CH3
C
O
OH
CH3NH2
AlCl3 Cl AlCl4
CH3NH2 HCl CH3NH3Cl
CH3Li H2O CH4 LiOH
+
+
+
+ +
I. +
II.
III.
IV.
Chapter 2 Acids and Bases
14
5. Which are acid-base reactions according to the Brønsted-Lowry theory? (Sec. 2.3)
a) I
b) I, III, IV
c) II, III
d) I, IV
6. Which are acid-base reactions according to Lewis theory but not according to the Brønsted-Lowry theory?
(Sec. 2.7)
a) I, II
b) III, IV
c) I, III, IV
d) I, II, III, IV
C
O
H3C CH3
CH3 C
O
H3C
CH3
CH3
H3C
C
O
OH
H2O H3C
C
O
O H3O
NH3 BF3 NH3BF3
O
H3C CH3BF3 O BF3
H3C
H3C
I.
II.
III.
IV.
+
+
+
+
+
+ +
+
+
+
+
+
IV.
III.
II.
I.
CH3NH2 HCl CH3NH3Cl
CH3NH2 BF3 CH3NH2BF3
Br2 FeBr3 FeBr4 Br
(CH3)3COH H2SO4 (CH3)3C H2O HSO4
Chapter 2 Acids and Bases
15
7. Which acid has the highest pKa? (Sec. 2.4)
a) CH3COOH
b) H2O
c) NH4
+
d) HCl
8. Arrange the following in order of increasing basicity (weakest to strongest). (Sec. 2.4)
I. OH- II. Cl- III. H2O IV. NH3
a) II, III, IV, I
b) III, I, IV, II
c) IV, I, II, III
d) III, IV, I, II
9. Arrange the following ions in the order of increasing acidity (weakest to strongest). (Sec. 2.4)
I. H2O II. H3O+ III. NH4
+
a) II, III, I
b) I, II, III
c) III, II, I
d) I, III, II
10. Which ion is the strongest base? (Sec. 2.4)
CH3CH2O a) b) C c) Cl d) CH3CH2
O
CH3 O
Chapter 2 Acids and Bases
16
11. Which equilibria lie considerably toward the right? (Sec. 2.5)
a) II, III
b) I, III, IV
c) III, IV
d) I, II, III
12. Which equilibria lie considerably toward the left? (Sec. 2.5)
a) II
b) I, IV
c) III, IV
d) I
C
O
H3C OH
NH3 C
O
H3C O
C
O
H3C O
C
O
H3C OH
NH4
H2O OH
NH4 OH NH3 H2O
HCN OH CN H2O
+
+
+
+
+
+
+
+
I.
II.
III.
IV.
C
O
H3C OH
NH3
C
O
H3C O
C
O
H3C O
C
O
H3C OH
NH4
NH4
OH NH3 H2O
HCN
CH3
CN
CH3OH
+
+
+
+
+
+
+
+
I.
II.
III.
IV. C
O
H3C OH
C
O
H3C O
Chapter 2 Acids and Bases
17
13. List the bonds in order of increasing acidity (least to most). (Sec. 2.6)
a) II, III, IV, I
b) III, I, II, IV
c) I, IV, II, III
d) IV, III, II, I
14. List the bonds in order of decreasing acidity (most to least). (Sec. 2.6)
a) I, III, II, IV
b) IV, II, III, I
c) II, III, IV, I
d) I, II, III, IV
15. Which substances are Lewis bases? (Sec. 2.7)
a) I, II
b) I, III
c) III, IV
d) I, IV
16. What is the stronger acid in the following reaction if the equilibrium constant is approximately 108. (Sec. 2.5)
17. What is the stronger acid in the following reaction if the equilibrium constant is much less than 0.01? (Sec. 2.5)
C H O H F H N H
I II III IV
F H Br H Cl H I H
I II III IV
H2O AlCl3
H3C
CH
CH3
F
I II III IV
HC CH + NH2 HC C + NH3
a) b) c) d)
HNO3 + H2SO4 H2NO3 + HSO4
a) b) c) d)
Chapter 2 Acids and Bases