Jeffrey Elbert
University of Northern Iowa
INTRODUCTION TO
ORGANIC CHEMISTRY
Third Edition
William Brown
Beloit College
Thomas Poon
Claremont McKenna, Pitzer, and Scripps Colleges
John Wiley & Sons, Inc.
, CONTENTS
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
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
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, Chapter 1 Covalent Bonding and Shapes of Molecules
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)
H H H
.. :O: ..
a) H C OH c) H
b) H
H .O. O.. H d) H O C O
.. .. H
H
.C. .C.
10. Which Lewis structures are correct? (Sec. 1.3)
H H H H
H O O H H N N H H N O H C Cl
H H
I II III IV
a) I, II
b) II, IV
c) III, IV
d) I, III
11. Which molecules are polar? (Sec. 1.5)
NH3 CO2 H2O CH4 Br2
I II III IV V
a) I, IV
b) I, III
c) II, III, IV
d) III, IV, V
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