Test Bank
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.
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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
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 O O HH C
O
O HOH.. .. ............
::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
O O HH N N
H
H
H
H N
H
H
H
O C
H
H
H
Cl
I II III IV
VIVIIIIII
Br2H2OCO2NH3 CH4
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)
VIVIIIIII
CH3OHH3C CH3CH2Cl2C
O
HHH2C CH2
C
O
O HC OC O H
hydroxyl I
carbonyl II
carboxyl III
IVIIIIII
NH4ClCH2 CH2CH3OHC
O
HH3C
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
d)c)
b)a)
H2C CH CH2 O CH3CH3 CH2 CH2 CH
OCH3 C
O
CH2 CH3CH3 CH
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 spI II III IV V
O C OHC NH2C CH2H2C O
CH4
CH3O
CH3
H2C O H2C O
H2C CH CH2 H2C CH CH2
N C O N C O
CH3CH2
OHI
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
OHH3CN CH3
CH3
HC
O
CH3H3CCH3 OHC
O
HH3C
Chapter 1 Covalent Bonding and Shapes of Molecules
7
31. Which of the following compounds contains a tertiary (3°) alcohol? (Sec. 1.8)
OHH3C
H3CCH3
C C
CH3
H3C
H3CCH2
OH
OHH3C
H3CHC
OHH3CHC
H3CCHCH3
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
HH
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
H3CHC
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
VIIIVIIVIV
IVIIIIII
+
+
+
+
H2C2H5ONaNaHC2H5OH
ClCH3OH2HClCH3OH
VIV
IVIII
III++
CH3OH HCl CH3OH2 Cl+ +
C2H5OH NaH C2H5ONa H2+ +
CH3CO2CH3NH3H3CCO2HCH3NH2
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
VIV
IVIII
III++
CH3OH HCl CH3OH2 Cl+ +
C2H5OH NaH C2H5ONa H2+ +
CH3CO2CH3NH3CH3CO2HCH3NH2
CH3C
O
OH3CNH3 CH3
C
O
OHCH3NH2
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
CH3H3CCH3 C
O
H3C
CH3
CH3
H3CC
O
OHH2O H3C
C
O
O H3O
NH3 BF3 NH3BF3
OH3C CH3 BF3 O BF3
H3C
H3C
I.
II.
III.
IV.
+
+
+
+
+
++
+
+
+
+
+
IV.
III.
II.
I.
CH3NH3ClHClCH3NH2
CH3NH2BF3BF3CH3NH2
BrFeBr4FeBr3Br2
HSO4H2O(CH3)3CH2SO4(CH3)3COH
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 d)c)b)a) CH3CH2ClC
O
OCH3
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
OHH3CNH3 C
O
OH3C
C
O
OH3CC
O
OHH3C
NH4
H2O OH
NH4 OH NH3 H2O
HCN OH CN H2O
+
+
+
+
+
+
+
+
I.
II.
III.
IV.
C
O
OHH3C
NH3
C
O
OH3C
C
O
OH3CC
O
OHH3C
NH4
NH4
OH NH3 H2O
HCN
CH3
CN
CH3OH
+
+
+
+
+
+
+
+
I.
II.
III.
IV. C
O
OHH3CC
O
OH3C
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 N HO H F H
I II III IV
F H Br H Cl H I H
I II III IV
H2O AlCl3H3C
CHCH3
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
18
18. Which is the stronger base if the equilibrium lies considerably to the right? (Sec. 2.5)
19. What is the role of diethyl ether in the following reaction? (Sec. 2.7)
a) Lewis acid b) Lewis base c) Brønsted acid d) Brønsted base
20. What is the role of water in the following reaction? (Sec. 2.3)
a) acid b) base c) conjugate acid d) conjugate base
21. What is the role of methanol in the following reaction? (Sec. 2.7)
a) Lewis acid b) Lewis base c) Brønsted acid d) Brønsted base
22. Which statements about acid-base equilibria are true? (Sec. 2.4) I. The pKa is the negative log10 of the acid equilibrium constant. II. A stronger acid has a pKa with a smaller value than a weaker acid. III. A stronger base has a conjugate acid which has a pKa with a smaller value than a weaker base. IV. The Ka = K [HA].
a) I, III b) I, II c) I, II, III d) II, III, IV
CH3CH2OCH2CH3 BF3 (CH3CH2)2O BF3+
NH3 H3O H2O NH4+ +
C
O
OHH3CC
O
OH3CHCNCN+ +
a) b) c) d)
C
CH3
H3C
CH3
CH3OH C
CH3
H3C
CH3
OCH3
H+
Chapter 2 Acids and Bases
19
23. Which is the order of decreasing acid strength of the following compounds (greatest first)? (Sec. 2.6)
C
O
OHCH2
Cl C
O
OHCH2
Br C
O
OHCH2
F C
O
OHCH2
H
I II III IV a) II, I, III, IV b) III, IV, I, II c) III, I, II, IV d) IV, II, I, III 24. Which is the order of increasing acid strength of the following compounds (least first)? (Sec. 2.6)
OH
O
FOH
OF
OH
O
FOH
OF
I II III IV a) I, III, II, IV b) IV, III, II, I c) II, I, III, IV d) IV, III, I, II
Chapter 2 Acids and Bases
20
25. Which is the proper reaction mechanism for the reaction of borontrifluoride and diethyl ether? (Sec. 2.7)
OCH2CH3CH3CH2 O
CH2CH3CH3CH2
BF3
OCH2CH3CH3CH2 O
CH2CH3CH3CH2
BF3
OCH2CH3CH3CH2 O
CH2CH3CH3CH2
BF3
OCH2CH3CH3CH2 O
CH2CH3CH3CH2
BF3
:BF3
BF3
+
-
..
.. -
+
:BF3
+
-
BF3 ....
-
+
a)
b)
c)
d)
Fill in the Blank 1. The weaker the acid, the ________________ the conjugate base. (Sec. 2.5) 2. The higher concentration (reactants or products) at equilibrium will lie on the side of the ___________ acid. (Sec. 2.5) 3. Complete the following reaction. (Sec. 2.3)
+ H2OCH3COHO
CH3CO-
O+
4. Complete the following reaction. (Sec. 2.3)
NH3 ++NH4Cl CH3CONa
O
5. Complete the following reaction. (Sec. 2.3)
+ H2O NH3 + H3O+ + Cl-
Chapter 2 Acids and Bases
21
6. Complete the following reaction. (Sec. 2.3)
+CH3COHO
CH3CONaO
+ NaHCO3
7. Complete the following reaction scheme with the appropriate equilibrium arrow (indicating the higher concentrations at equilibrium). (Sec. 2.5)
+ HCNCH3CONa
O
CH3COH
O+ NaCN
8. Complete the following reaction scheme with the appropriate equilibrium arrow (indicating the higher concentrations at equilibrium). (Sec. 2.5)
+NaH2PO4 NaHCO3 Na2PO4 + H2CO3
9. Identify the acid, base, conjugate acid, conjugate base in the following reaction. (Sec. 2.3)
NaCN + NaHSO4 HCN + Na2SO4
10. Identify the acid, base, conjugate acid, conjugate base in the following reaction. (Sec. 2.3)
+ +NaHCO3NH4Cl NH3 H2CO3 + NaCl
True-False 1. Brønsted-Lowry acids accept protons when reacting. (Sec. 2.3) 2. Lewis bases donate electrons when reacting. (Sec. 2.7) 3. The stronger acid has the larger (more positive) pKa. (Sec. 2.4) 4. Strong acids have weak conjugate bases. (Sec. 2.4) 5. The equilibrium will lie to the right in the following reaction. (Sec. 2.5)
+ +NH4Cl NH3 +H2O H3O+ Cl-
6. The equilibrium will lie to the right in the following reaction. (Sec. 2.5)
+ NaH2PO4HCN H3PO4 + NaCN
Chapter 2 Acids and Bases
22
7. Water acts as a base in the following reaction. (Sec. 2.3)
+NH3 H2O NH4OH 8. Ammonia acts as a Brønsted-Lowry base in the following reaction. (Sec. 2.3)
+NH4Cl NaHCO3 NH3 + H2CO3 + NaCl
9. The strongest acid in the following list is sodium bicarbonate. (Sec. 2.4)
NH4Cl NaHCO3 H2O CH3CH2OH 10. The weakest acid in the following list is acetic acid. (Sec. 2.6)
CH3COH
OClCH2COH
O
FCH2COH
O
FCH2CH2COH
O
Chapter 2 Acids and Bases
23
Answers Multiple Choice 1. d 2. a 3. b 4. d 5. d 6. b 7. d 8. a 9. d 10. d 11. b 12. a 13. c 14. b 15. d 16. a 17. c 18. b 19. b 20. d 21. b 22. b 23. c 24. b 25. b Fill in the Blank 1. stronger 2. weaker 3. H3O+ 4. CH3COOH + NaCl 5. NH4Cl 6. Na2CO3 7. equilibrium arrow pointed to the left 8. equilibrium arrow pointed to the left 9. base, acid, c.acid, c. base 10. acid, base, c. base, c. acid True-False 1. F 2. T 3. F 4. T 5. F 6. F 7. F 8. T 9. F 10. T
Chapter 4 Alkenes and Alkynes
36
Multiple Choice 1. Which are the approximate carbon-carbon bond angles at positions I and II in the following compound? (Sec. 4.2)
a) 109°, 109° b) 120°, 180° c) 120°, 109° d) 109°, 120°
2. Which is the best description for the indicated bond in the following compound? (Sec. 4.2)
a) sp3-sp3 b) sp3-sp3 and 2p-2p c) sp2-sp2 and ҏ2p-2p d) sp-sp and sp-sp
3. Which is the IUPAC name for the following structure? (Sec. 4.3)
a) 3,3-dimethyl-4-pentene b) 3-methyl-3-ethyl-1-butene c) isopropylpentene d) 3,3-dimethyl-1-pentene
4. Which is the correct structure for vinylcyclobutane? (Sec. 4.3)
CH3I
II
CH3
CH3C
CH2
CH
CH3
CH2
CH2 CH2 CH CH2
a) b) c) d)
CH3
Chapter 4 Alkenes and Alkynes
37
5. Which is the correct name for the following compound? (Sec. 4.3)
a) 2E, 5E-5-methyl-2,5-heptadiene b) 2E, 5E-3-methyl-2,5-heptadiene c) 2Z, 5E-3-methyl-2,5-heptadiene d) 2E, 5Z-5-methyl-2,5-heptadiene
6. Which is the correct name for the following compound? (Sec. 4.3)
a) 1,3-dimethylcyclohexene b) 2,4-dimethylcyclohexene c) 3,5-dimethylcyclohexene d) 2,4-dimethyl-1-cyclohexene
7. Which is the correct name for the following compound? (Sec. 4.3)
a) E-2-ethyl-2-butene b) Z-3-methyl-3-pentene c) E-3-methyl-2-pentene d) Z-3-ethyl-2-butene
8. Which is the IUPAC name for the following compound? (Sec. 4.3)
a) dimethyl acetylene b) 3-butyne c) 3-butene d) 2-butyne
H3CC
CCH2
CC
CH3
CH3
H H
H
CH3
CH3
C C
H3C
H
CH3
CH2CH3
C C CH3H3C
Chapter 4 Alkenes and Alkynes
38
9. Which is the IUPAC name for the following compound? (Sec. 4.3)
a) 1,1-dimethyl-4-ethyl-2,5-cyclohexadiene b) 1-ethyl-4,4-dimethyl-2,5-cyclohexadiene c) 3-ethyl-6,6-dimethyl-1,4-cyclohexadiene d) 6-ethyl-3,3-dimethyl-1,4-cyclohexadiene
10. Which of the following alkenes do not show cis-trans isomerization? (Sec. 4.3)
I) 2-methyl-2-hexene II) 1-chloro-1-butene III) 1-methylcyclohexene IV) 2-methyl-3-hexene
a) I, II b) III, IV c) II, III, IV d) I, III
11. Which of the following alkenes show cis-trans isomerization? (Sec. 4.3)
I) 1-chloropropene II) 3-methylcyclohexene III) 2,6-dimethyl-2,5-octadiene IV) 3-ethyl-3-methyl-1-pentene
a) I, II b) II, III c) III, IV d) I, III
12. How many trans isomers are there for an alkene with the formula, C4H7Cl? (Sec. 4.3)
a) 2 b) 3 c) 6 d) 8
13. How many cycloalkanes of molecular formula C5H10 show cis-trans isomerism? (Sec. 4.3)
a) 1 b) 2 c) 3 d) 4
H3C
H3C
CH2CH3
Chapter 4 Alkenes and Alkynes
39
14. How many cycloalkanes of molecular formula C6H12 do not show cis-trans isomerization? (Sec. 4.3)
a) 2 b) 3 c) 4 d) 5
15. Arrange the following groups in the order of increasing priority (lowest first). (Sec. 4.3)
a) I, II, IV, III b) III, IV, II, I c) I, IV, II, III d) IV, II, III, I
16. Arrange the following groups in the order of increasing priority (lowest first). (Sec. 4.3)
a) IV, III, II, I b) I, II, III, IV c) III, IV, I, II d) III, I, IV, II
17. Arrange the following groups in the order of increasing priority (lowest first). (Sec. 4.3)
a) II, I, IV, III b) II, III, I, IV c) I, II, IV, III d) III, IV, II, I
CH2CH3 CH2NH2 CH2Br CH2OH
I II III IV
CH CH2 C CH C N C O
CH3
IVIIIIII
C
O
OCH3 C
O
OH C
O
CH3 C
O
NH2
IVIIIIII
Chapter 4 Alkenes and Alkynes
40
18. Which structure is Z-2-bromo-3-methyl-2-pentene? (Sec. 4.3)
19. Which alkenes have E configurations? (Sec. 4.3)
a) I, II b) II, III c) III, IV d) II, IV
20. How many cis-trans isomers are possible for geraniol? (Sec. 4.3 and 4.5)
a) 2 b) 3 c) 4 d) 6
21. How many distinct terpene structure types can be made from the assembly of 2-isoprene units? (Sec. 4.5)
a) 1 b) 2 c) 3 d) 4
C C
H3C
Br
CH2CH3
CH3
C C
Br
CH
CH3
CH2CH3H
HC C
H3C
Br
CH3
CH2CH3
C C
H3C
H3C
Br
CH2CH3
a) b) c) d)
C C
C C
H H
O
HO
O
OH
C C
Cl
H
CH2Cl
CH3
C C
H3C
H2C F
Cl
Cl
C C
Br
H3C
Cl
I
I II III IV
C
CH3
CCH2OH
HH2C
H2CCH
CCH3H3C
Chapter 4 Alkenes and Alkynes
41
22. How many isoprene units are there in vitamin A? (Sec. 4.5)
a) 2 b) 3 c) 4 d) 8
23. Cleavage of which of the indicated bonds in limonene leads to a head to tail terpene? (Sec. 4.5)
24. Arrange the following compounds in decreasing order of boiling point (highest first). (Sec. 4.4)
a) I, II, IV, III b) II, IV, III, I c) III, IV, II, I d) IV, II, III, I
25. Arrange the following molecules in order of increasing boiling point (lowest first). (Sec. 4.4)
a) I, II, IV, III b) IV, II, III, I c) III, IV, II, I d) I, II, III, IV
CH2OH
a)
b)
c)
d)
I II III IV
C CH3C CH2CH2CH3 C CH3C CH
CH3
CH3
HC C C
CH3
CH3
CH3
C CH3C CH3
I II III IV
Chapter 4 Alkenes and Alkynes
42
Fill in the Blank 1. The IUPAC name of the following molecule is ____________________________________________________. (Sec. 4.3)
2. The IUPAC name of the following molecule is ____________________________________________________. (Sec. 4.3)
3. The structure of (3E, 6Z) 2,9-dimethyl-3,6-decadiene is
(Sec. 4.3) 4. The structure of 3,7-diethyl-4,8-dimethyl-1,5-cyclooctadiene is
(Sec. 4.3) 5. The IUPAC name of the following molecule is ____________________________________________________. (Sec. 4.3)
Chapter 4 Alkenes and Alkynes
43
6. The structure of 2-cyclobutyl-6,6-dimethyl-4-octyne is
(Sec. 4.3) 7. The approximate bond angles of the indicated carbons are 1) ______, 2) _______, 3) _______, 4) ______. (Sec. 4.2)
1
34
2
8. The number of isoprene units in menthol is ___________. (Sec. 4.5)
OH
9. The number of isoprene units in grandisol is ____________. (Sec. 4.5)
OH
H
10. The priority order of the groups –CH2CH3, -CH3, -OCH3, -CH=CH2 is;
> > > (Sec. 4.3)
Chapter 4 Alkenes and Alkynes
44
True-False 1. The structure of 4-isopropyl-1-methylcyclohexene is
(Sec. 4.3) 2. The name of the following structure is (3E, 5E) 2-ethyl-3,5-octadiene. (Sec. 4.3)
3. The following compounds are listed in order of increasing boiling point (lowest first). (Sec. 4.4)
< < <
4. The following groups are listed in order of decreasing priority (highest first). (Sec. 4.3)
CH
CH3
CH3
CH
CH2 CH3C CH > > >
5. The following groups are listed in order of increasing priority (lowest first). (Sec. 4.3) O
H OCH2CH3
O
Cl Cl< < <
6. The following structures represent identical compounds. (Sec. 4.3)
7. The following structures represent isomers. (Sec. 4.3)
8. 2,2-Dimethylcyclohexene occurs as E and Z isomers. (Sec. 4.3)
Chapter 4 Alkenes and Alkynes
45
9. 2,3-dimethyl-3-hexene occurs as E and Z isomers. (Sec. 4.3) 10. There are 4 possible E,Z isomers of 1,3-pentadiene. (Sec. 4.3)
Chapter 4 Alkenes and Alkynes
46
Answers Multiple Choice 1. c 2. c 3. d 4. d 5. b 6. c 7. c 8. d 9. d 10. d 11. d 12. b, two alkenes and a cycloalkane 13. a 14. d 15. a 16. b 17. d 18. c 19. c 20. a 21. c 22. c 23. a 24. a 25. c Fill in the Blank 1. (Z) 7-methyl-3-nonene 2. 6,6-dimethyl-1,4-cycloheptadiene 3.
4.
5. 2,8,9-trimethyl-3-decyne
Chapter 4 Alkenes and Alkynes
47
6.
7. 1) 120, 2) 109, 3) 120, 4) 180 8. 2 9. 2 10.
OCH3 CH
CH2 CH2CH3 CH3> > >
True-False 1. F 2. F 3. F 4. F 5. T 6. T 7. F 8. F 9. T 10. F
Chapter 5 Reactions of Alkenes
48
Multiple Choice 1. The reaction of propene with which of the following reagents are oxidation reactions? (Sec. 5.3 - 5.5)
HBr/CH2Cl2 OsO4 H2/Pt Br2 H+/H2O I II III IV V
a) II b) III c) I and V d) II and IV
2. Which point on the potential energy diagram represents the intermediate? (Sec. 5.2)
3. Which diagram represents the slowest reaction? (Sec. 5.2)
E
reaction coordinate
A
B
CD
E E
E E
reaction coordinateA
reaction coordinateB
reaction coordinate reaction coordinateC D
Chapter 5 Reactions of Alkenes
49
4. Which compound has the highest heat (most negative) of hydrogenation? (Sec. 5.5)
5. Which statement does not describe a transition state? (Sec. 5.2)
a) Possesses a definite geometry b) Maximum on the potential energy diagram c) Structure can be determined experimentally d) Can not be isolated
6. Using Markovnikov’s rule, predict the position of the Cl atom in the major product from the reaction of 1-methylcyclohexene with HCl. (Sec. 5.3)
7. Which species are electrophiles? (Sec. 5.3)
a) II, III b) II, IV c) I, IV d) I, III
8. Arrange these carbocations in order of increasing stability (least to most). (Sec. 5.3)
a) I, II, III, IV b) III, I, II, IV c) II, IV, I, III d) I, III, IV, II
A
B
C
D
H3C
I II III IV
A B C D
NH3
I II III IV
OH H
Chapter 5 Reactions of Alkenes
50
9. Arrange these carbocations in order of increasing stability (least to most). (Sec. 5.3)
a) I, II, III b) I, III, II c) II, I, III d) III, II, I
10. Which reagents react with an alkene by syn addition? (Sec. 5.3 - 5.5)
I. Cl2 II. Br2 III. H2/Pt IV. OsO4/ROOH
a) I, II b) III, IV c) II, III d) I, IV
11. Which reagents react with an alkene by anti addition? (Sec. 5.3 - 5.5)
I. Cl2 II. Br2 III. H2/Pt IV. OsO4/ROOH
a) I, II b) III, IV c) II, III d) I, IV
12. Which reagents react with an alkene in a Markovnikov orientation? (Sec. 5.3)
I. HBr II. H2O/H2SO4 III. Br2 IV. OsO4/ROOH
a) I, II b) III, IV c) II, IV d) II, III, IV
13. Which is the major product from the reaction of propene with OsO4/ROOH? (Sec. 5.4)
a) 1-propanol b) 2-propanol c) 1,2-propanediol d) 1,3-propandiol
14. Which reagents react with an alkene by an electrophilic mechanism? (Sec. 5.3)
I. H2O/H2SO4 II. Br2/CCl4 III. HBr IV. H2/Pt
a) I, II, III b) I, II, IV c) II, IV d) III, IV
I II III
Chapter 5 Reactions of Alkenes
51
15. Which is the product of the reaction of 1-methylcyclohexene with H2O/H2SO4? (Sec. 5.3)
16. Which is the major product from acid catalyzed hydration of 2-methyl-2-pentene? (Sec. 5.3)
a) 2-methyl-3-pentanol b) 2-methyl-2-pentanol c) 4-methyl-2-pentanol d) 3-methyl-3-pentanol
17. Which is the intermediate formed in the reaction of propene with HBr? (Sec. 5.3)
18. Which is the major product from the reaction of cyclopentene with Br2/CCl4? (Sec. 5.3)
19. Compound A has a molecular formula C8H14 and reacts with H2/Pt to give compound B, C8H16. Which is compound A? (Sec. 5.5)
CH3
OHOH
CH3
OH
CH3
OH
H
HOH
CH3
HH
a) b) c) d)
Br
Br
a) b) c) d)
Br
H
H
Br
Br
H
H
Br
H
Br
Br
Br
a) b) c) d)
a) b) c) d)
Chapter 5 Reactions of Alkenes
52
20. Which is the major product from the reaction of 1,2-dimethylcyclohexene with D2/Pt? (Sec. 5.5)
21. Which alkene has the highest rate of reaction with HBr? (Sec. 5.3)
22. Which potential energy diagram represents the reaction of HBr with 2-butene? (Sec. 5.2)
23. Which compound does not give two isomers when reacted with Cl2/CCl4? (Sec. 5.3)
a) b) c) d)
a) b) c) d)
CH3
DD
CH3
CH3
DCH3
D
D
CH3CH3
D
CH3D
CH3
D
a) b) c) d)
E E
E E
reaction coordinate reaction coordinate
reaction coordinate reaction coordinate
A B
C D
Chapter 5 Reactions of Alkenes
53
24. Which compound has the lowest (least negative) heat of hydrogenation? (Sec. 5.5)
25. Which point on the potential energy diagram represents the activation energy? (Sec. 5.2)
a) b) c) d)
E
reaction coordinate
A
B
CD
Chapter 5 Reactions of Alkenes
54
Fill in the Blank 1. The stereoselective reagents from the following list are _________________________________. (Sec. 5.3-5.5)
HCl H+/H2O Br2 OsO4 H2 2. Complete the following reaction by providing the major product. (Sec. 5.4)
OsO4
CH3COOH
3. Complete the following reaction by providing the major product. (Sec. 5.3)
HBr
CH2Cl2
4. Complete the following reaction by providing the major product. (Sec. 5.5)
H2
Pt
5. Complete the following reaction by providing the necessary reagents. (Sec. 5.3)
Br
Br
6. Complete the following reaction by providing the necessary reagents. (Sec. 5.3)
OH
Chapter 5 Reactions of Alkenes
55
7. Complete the following reaction by providing the starting material and reagents. (Sec. 5.3)
Cl
Cl
8. Complete the following reaction by providing the starting materials. (Sec. 5.5)
H2
Ptor
9. Draw the intermediate of the following reaction. (Sec. 5.3)
+ HCl
10. Draw the intermediate of the following reaction. (Sec. 5.3)
+ Br2
11. Draw the reaction arrows (curved arrows) for the following reaction. (Sec. 5.3)
H Cl C+
HClCl
+
Chapter 5 Reactions of Alkenes
56
True-False
A
BC
D
E
E
reaction coordinate 1. The reaction represented by the above reaction energy diagram is endothermic. (Sec. 5.2) 2. The rate determining step of the reaction represented by the above reaction energy diagram is the first step. (Sec. 5.2) 3. The activation energies of the reaction represented by the above reaction energy diagram are noted as A and B. (Sec. 5.2) 4. The following carbocations are listed in increasing order of stability (least first). (Sec. 5.3)
C+
H
CH3
C+
CH3
CH3 C+
H
H< <
5. The following alkenes are listed in decreasing order of heat of hydrogenation (highest first). (Sec. 5.5)
> > >
6. The product of the reaction of cyclohexene and bromine is cis-1,2-dibromocycloheane. (Sec. 5.3) 7. The major product of the reaction of catalytic hydrogenation of 1,2-dimethylcyclohexene is cis-1,2-dimethylcyclohexane. (Sec. 5.5)
Chapter 5 Reactions of Alkenes
57
8. Bromination, catalytic hydrogenation, and hydroxylation via osmium tetroxide are cis stereoselective reactions. (Sec. 5.3-5.5) 9. Hydrohalogenation, hydration, and bromination reactions proceed through an open carbocation intermediate. (Sec. 5.3) 10. The reaction arrows (curved arrows) are accurately drawn for the following reaction. (Sec. 5.3)
H Br
H BrH+ Br-
Chapter 5 Reactions of Alkenes
58
Answers Multiple Choice 1. d 2. c 3. a 4. b 5. c 6. c 7. c 8. b 9. d 10. b 11. a 12. a 13. c 14. a 15. b 16. b 17. d 18. a 19. a 20. b 21. d 22. c 23. a 24. d 25. d Fill in the Blank 1. Br2, OsO4, H2 2.
OH
OH 3.
Br
4.
H H
Chapter 5 Reactions of Alkenes
59
5. Br2
CH2Cl2 6.
H+
H2O 7.
Cl2
CH2Cl2 8.
or
9.
+ 10.
Br +
11.
H Cl C+
HClCl
+
Chapter 5 Reactions of Alkenes
60
True-False 1. F 2. F 3. T 4. F 5. F 6. F 7. T 8. F 9. F 10. F
Chapter 6 Chirality
61
Multiple Choice 1. Which compounds contain stereocenters? (Sec. 6.3)
I) 1-chloropentane II) 2-chloropentane III) 3-chloropentane IV) 1,2-dichloropentane
a) I, II b) III, IV c) I, III d) II, IV
2. Which compounds contain stereocenters? (Sec. 6.3)
I) 2-methylpentane II) chlorocyclohexane III) 3-methyl-2-butanol IV) 2-hydroxypropanoic acid
a) I, II b) III, IV c) I, III d) II, IV
3. Which compounds contain stereocenters? (Sec. 6.3)
a) I, II b) III, IV c) I, III d) II, IV
HO OH CH
OH
CH2
OH
CH3CCH2CH3
O
CHCHCH3
OHH3C
H3C
I. II.
III. IV.
Chapter 6 Chirality
62
4. Which compounds have multiple stereocenters? (Sec. 6.3, 6.5)
a) I, II b) III, IV c) II, III d) I, III
5. How many stereoisomers are possible for 1,2-dichlorocyclopentane? (Sec. 6.3)
a) 1 b) 2 c) 3 d) 4
6. How many stereoisomers are possible for 2,3-butanediol? (Sec. 6.3)
a) 1 b) 2 c) 3 d) 4
7. How many stereoisomers are possible for the following structure? (Sec. 6.2-6.3)
a) 1 b) 2 c) 3 d) 4
IV.III.
II.I.
CHO
CH2COH
CH2
COH
O
O
COH
O
CH3CHCHCH3
Cl OH
CH3CHCH COH
HO OH OCH3CHCHCH3
CH3HO
CH3CHCHCOH
O
NH2
OH
Chapter 6 Chirality
63
8. Which structures are chiral? (Sec. 6.3)
a) I, II, V b) I, II c) II, II, IV d) III, IV
9. Which pair of structures are enantiomers? (Sec. 6.3)
a) I, II b) II, III c) I, III d) I, II, III
CH3
OHHOC
H
O
Br CH3
Cl
CH2CH3
H
COHH3C
HO
O
Br
ClH3CH2C
H3C
I CH3
H
OHI OH
CH3
H
I.
II.
III.
V.IV.
III.II.I.
H2C CCH2CH2CH2
Cl
HH2C C
CH2CHCH3
Cl
H
C CCl
H
H
CH2CH2CH3
H2C CCHCH2CH3
Cl
H
H2C CCl
CH2CH2CH3
Chapter 6 Chirality
64
10. What is the relationship between these two structures? (Sec. 6.3, 6.5)
a) Identical structures b) Enantiomers c) Diastereomers d) Constitutional isomers
11. What is the relationship between these two structures? (Sec. 6.3, 6.5)
a) identical structures b) enantiomers c) diastereomers d) constitutional isomers
CH3
NH2H
CH3H
NH2
H
CH3H2N
NH2H3C
H
H
Br Cl
H H
Br
Cl
H
Chapter 6 Chirality
65
12. Which are meso compounds? (Sec. 6.5)
a) I, II b) I, III c) II, III d) III, IV
13. How many stereoisomers are possible for Prilosec? (Sec. 6.7)
NNH
O
CH3 CH3
O OH
.HCl
a) 4 b) 8 c) 16 d) 32
CH2OH
OHH
OHH
CH2OCH3
CH
OHH
OHH
CH
O
O
CH2OH
OCH3H
OCH3H
CH2OH
CH2OH
OCH3H
HH3CO
CH2OH
I. II.
III. IV.
Chapter 6 Chirality
66
14. How many pairs of enantiomers are possible for cortisone acetate? (Sec. 6.7)
O
CH3
O CH3 O
O
OOH
a) 32 b) 64 c) 128 d) 256
15. Which forms of lactic acid are R forms? (Sec. 6.4)
a) I, II b) III, IV c) I, III d) II, IV
16. What is the R,S configuration for the following structure of isocitric acid? (Sec. 6.4)
a) 2-R, 3-R b) 2-R, 3-S c) 2-S, 3-R d) 2-S, 3-S
COH
HH3CHO
O
CH3
OHHOCH
O
COH
CH3HHO
OCH3
COHHOH
O
I. II. III. IV.
C
CCOH
HOCCH2
H
HCOH
HO
O
O
O
#1
Chapter 6 Chirality
67
17. The specific rotation of dextrorotatory tartaric acid is +12.7 degrees. A mixture of dextrorotatory and levorotatory tartaric acid has a specific rotation of +6.35 degrees. What is the optical purity of the mixture? (Sec. 6.9)
a) 25% b) 33 1/3% c) 50% d) 75%
18. Rank the following substituents in order of increasing priority. (Sec. 6.4)
a) I, III, II, IV b) II, I, III, IV c) III, I, II, IV d) IV, III, I, II
19. Rank the following substituents in order of increasing priority. (Sec. 6.4)
a) III, II, IV, I b) I, IV, II, III c) IV, I, III, II d) I, II, III, IV
20. Rank the following substituents in order of decreasing priority (highest first). (Sec. 6.4)
a) II, III, IV, I b) III, IV, I, II c) IV, III, II, I d) IV, I, II, III
OH Cl CH3 H
I. II. III. IV.
IV.III.II.I.
C CH
H
HOH OCH3 C O
H
OCH3 COH
OCH
OOCH2CH3
IV.III.II.I.
Chapter 6 Chirality
68
21. Rank the following substituents in order of increasing priority. (Sec. 6.4)
a) III, II, IV, I b) IV, I, II, III c) I, III, II, IV d) IV, II, I, III
22. Which structures represent R-3-methylhexane? (Sec. 6.4)
a) II, III b) I, III c) I, II d) III, IV
23. Which structure is correctly named 3R,4S-3,4-dimethylhexane (Sec. 6.4)
a) II b) I, III c) III d) III, IV
24. Which statement about enantiomers is false? (Sec. 6.8)
a) enantiomers have the same boiling and melting points. b) enantiomers have the same chemical properties. c) enantiomers have the same atom connectivity. d) enantiomers have the same three dimensional orientation.
I. II. III. IV.
C CH
H
HC CH3
CH3
CH3
C H
CH3
CH3
C CH3C
H
H
H3C
CH3H
HH
H3C
H3C
H
IV.III.II.I.
H CH3
H CH3
H3C H
H3C H
IV.III.II.I.
H CH3H
CH3H CH3H3C H
Chapter 6 Chirality
69
25. Which statements about stereoisomers are true? (Sec. 6.8, 6.9)
I) enantiomers and diastereomers have the same physical properties. II) 50/50 mixtures of R and S enantiomers are called racemic mixtures. III) meso isomers rotate the plane of plane polarized light. IV) dextrorotatory compounds rotate plane polarized light to the right.
a) I, II b) II, III c) II, IV d) III, IV
Fill in the Blank 1. The following structure contains ___________ stereocenters. (Sec. 6.7)
OH
OHO
N
OH
Nadolol (beta-blocker)
2. The following structure contains __________ stereocenters. (Sec. 6.7)
O OH
NCH3
morphine
3. The priority order for the following groups are (highest = 1),
CCH3
CH3CH3
C CCH3
H
HC C H C
CH3
HCH3
(Sec. 6.4)
Chapter 6 Chirality
70
4. The priority order for the following groups is (highest = 1),
CCl
ClCH3
CBr
HCH3
CCl
OHCH3
COH
HCH3
(Sec. 6.4) 5. The following structure is the _____________ configuration. (Sec. 6.4)
OH
OH 6. The following structure is the _____________ configuration. (Sec. 6.4)
OH
Br
NH2
7. The structure of the R,R enantiomer of 2,3-butanediol is,
(Sec. 6.4) 8. The structure of the S,R enantiomer of 3-bromo-4-chlorohexane is,
(Sec. 6.4)
Chapter 6 Chirality
71
9. The following structures are __________________ (what type of stereoisomer). (Sec. 6.3, 6.5)
NH2OH NH2OH
10. The following structures are ________________ (what type of stereoisomer). (Sec. 6.3, 6.5)
True-False 1. The following structures are enantiomers. (Sec. 6.3)
H
CH3OHCl
Cl
CH3OHH
2. The following structures are diastereomers. (Sec. 6.5)
Br Cl Cl Br
3. The name of the following structure is 2S,3S-2,3-dibromobutane. (Sec. 6.4)
Br
Br 4. The diastereomer of 2R,3R-dichlorobutane is achiral. (Sec. 6.5) 5. The following groups are listed in decreasing order of priority. (Sec. 6.4)
OH OCH3
O
CH3
O
OH> > >
Chapter 6 Chirality
72
6. The following groups are listed in decreasing order of priority. (Sec. 6.4)
OH NH2 Br CH3> > >
7. Enantiomers have the same physical properties (m.p., b.p., index of refraction, density). (Sec. 6.8) 8. Meso compounds rotate plane polarized light the same magnitude as enantiomers, but in opposite directions. (Sec. 6.5) 9. Diastereomers are achiral. (Sec. 6.5) 10. Enantiomers and meso compounds are diastereomers. (Sec. 6.5)
Chapter 6 Chirality
73
Answers Multiple Choice 1. d 2. b 3. d 4. c 5. c 6. c 7. d 8. d 9. a 10. a 11. c 12. c 13. b 14. a 15. a 16. b 17. c 18. d 19. b 20. d 21. d 22. c 23. c 24. d 25. c Fill in the Blank 1. 3 2. 5 3. 2, 3, 1, 4 4. 2, 1, 3, 4 5. 2R, 3R 6. 1S, 2S 7.
OH
OH 8.
Br
Cl
9. enantiomers 10. diastereomers
Chapter 6 Chirality
74
True-False 1. T 2. T 3. F 4. T 5. F 6. F 7. T 8. F 9. F 10. T
Chapter 7 Haloalkanes
75
Multiple Choice
1. Which of the following structures have the correct IUPAC name? (Sec. 7.2)
a) I, II
b) III, IV
c) I, III
d) II, IV
2. Which of the following structures have correct common names? (Sec. 7.2)
a) I, II
b) III, IV
c) I, III
d) II, IV
C
Cl
CH3
CH2CH2CH3H
CH3
F
OCH3H
Br
Br
HH3CO
C
CH3
CH2CH3
FCl
R-2-chloropentane
I
R-4-fluoro-4-methylcyclohexene
II
meso-1,2-dibromo-1,2-dimethoxyethane
III
S-2-chloro-2-fluorobutane
IV
H2C CHCH2F CHCH2Br
H3C
H3C
HCCl3 H3C CH
I
CH2CH3
allyl fluoride
I
isobutyl bromide
II
methylene chloride
III
isopropyl iodide
IV
Chapter 7 Haloalkanes
76
3. Which of the following compounds are secondary halides? (Sec. 7.6)
I) Isobutyl bromide II) 2-iodobutane III) isopropyl fluoride IV) neopentyl chloride
a) I, II
b) III, IV
c) II, III
d) I, IV
4. Which compounds are primary halides? (Sec. 7.6)
a) I, II
b) III, IV
c) II, III
d) I, IV
5. Which of the following halides is prepared from the following reactions? (Sec. 7.1, 5.3)
6. Which is the best reaction condition for preparing 2-iodohexane from 1-hexene? (Sec. 7.1, 5.3)
a) I2 / CCl4
b) HI
c) NaI
d) HIO4
H3C C C
I
CH3
CH3
H
C Cl
CH3
H3C
CH3
H3C CH2 CBr3 FH2C CH2 CH
CH3
CH3
I II III IV
HBr
Br
Br
Br Br
Br
a) b) c) d)
Chapter 7 Haloalkanes
77
7. Arrange the nucleophiles in order of increasing reactivity (least first). (Sec. 7.6)
a) I, IV, II, III
b) IV, II, I, III
c) II, I, III, IV
d) IV, III, I, II
8. Arrange the nucleophiles in order of increasing reactivity (least first). (Sec. 7.6)
a) III, II, I, IV
b) IV, I, II, III
c) I, III, II, IV
d) III, I, IV, II
9. Arrange the leaving groups in order of increasing leaving group ability (least first). (Sec. 7.6)
a) I, III, II, IV
b) III, I, IV, II
c) VI, II, I, III
d) IV, III, II, I
10. Arrange the leaving groups in order of increasing leaving group ability (least first). (Sec. 7.6)
a) IV, I, III, II
b) III, I, IV, II
c) II, IV, I, III
d) II, III, I, IV
BrH3COH3CCO
O
H2O
I II III IV
BrH3COH3CCO
O
HO
I II III IV
ICl Br F
IVIIIIII
IVIIIIII
CH3OOHH2ONH3
Chapter 7 Haloalkanes
78
11. Arrange the alkyl halides in order of increasing reactivity in an SN2 reaction with KI in acetone (least first).
(Sec. 7.6-7.7)
a) I, IV, III, II
b) IV, I, III, II
c) II, III, I, IV
d) III, II, IV, I
12. Which are optimum conditions for an SN2 reaction? (Sec. 7.6-7.7)
a) I, II
b) II, III
c) III, IV
d) I, IV
CH2CH2Br Cl CCH3
CH3
Cl
Br
I II III IV
I.
II.
III.
IV.DMSO
DMSO
H2O
acetone
NaI
CH3S Na
CH3OH
NaSH+
+
+
+CH2Br
CH3
Cl
Cl
CH2Cl
Chapter 7 Haloalkanes
79
13. Which nucleophilic substitution reactions will proceed? (Sec. 7.6-7.7)
a) I, II
b) II, III
c) III, IV
d) I, IV
14. Which reactions will proceed with inversion of configuration? (Sec. 7.6-7.7)
a) I, II
b) III, IV
c) II, III
d) I, IV
15. Which solvents are polar aprotic? (Sec. 7.6)
I) DMSO
II) H2O
III) Acetone
IV) Formic acid
a) II, III
b) III, IV
c) I, III
d) II, IV
IV.
III.
II.
I. NaCl CH3CH2OH
NH3 Br
CH3CH2O CH3CH2CH2Cl
LiCl CH4
+
+
+
acetone
ethanol
acetone
NaCl
NH3 Br
LiCl CH4
+
+
+
+
acetone
ethanol
ethanol
acetone
OCH2CH3
CH3CH2OH
NaSCH3
CH3OH
heatCH3CH2OH
OH
R-2-bromohexane
R-2-bromohexane
S-2-iodobutane
R-3-bromo-3-methylhexane
I. II.
III. IV.
acetone
Chapter 7 Haloalkanes
80
16. Arrange the alkyl halides in order of increasing rate of solvolysis (slowest first)? (Sec. 7.6)
a) IV, III, II, I
b) I, II, III, IV
c) III, II, I, IV
d) II, III, I, IV
17. Which conditions are optimum for an SN1 reaction? (Sec. 7.6-7.7)
18. Which solvents are polar protic? (Sec. 7.6)
I) ethanol
II) hexane
III) DMSO
IV) water
a) III, IV
b) II, III
c) I, IV
d) I, III
IVIIIIII
CH3CH2CH2ClCHCl
H3CH2C
H3CH2C
CHCl
H3C
H3C
CCl
CH3
H3C
CH3
d)
c)
b)
a)
NaCN
NaSH
CH3OH
NaCN
DMSO
DMSO
H2O
acetone
+
+
+
+
CCl
CH3
H3C
CH3
CH3CH2CH2Br
CHCl
H3C
H3C
CH3CH2Cl
Chapter 7 Haloalkanes
81
19. Which statements apply to an SN1 reaction? (Sec. 7.6)
I) The rate limiting step of the reaction involves the alkyl halide and the nucleophile.
II) The order of reactivity is methyl > 1°>2°>3°.
III) The rate limiting step of the reaction involves only the alkyl halide.
IV) There is an intermediate carbocation.
a) I, II
b) III, IV
c) I, IV
d) III
20. Which statements apply to an SN2 reaction? (Sec. 7.6)
I) The rate limiting step of the reaction involves the alkyl halide and the nucleophile.
II) The order of reactivity is methyl > 1°>2°>3°.
III) The rate limiting step of the reaction involves only the alkyl halide.
IV) There is an intermediate carbocation.
a) I, II
b) III, IV
c) I, IV
d) II, IV
21. Which conditions are optimum for an E2 reaction? (Sec. 7.8-7.9)
22. What is the major product from an elimination reaction starting with 2-bromopentane? (Sec. 7.8-7.9)
a) 1-pentene
b) cis-2-pentene
c) trans-2-pentene
d) a mixture of cis and trans-2-pentene
d)
c)
b)
a)
H2O
H2O
DMSO
DMSO
+
+
+
+
CH3OCH3CHCH2Br
CH3
CH3OHCH3CHCH2Cl
CH3
CH3CO K
CH3
CH3
CH3CHCl
CH3
FCH3I
Chapter 7 Haloalkanes
82
23. Which alkyl halide leads to the product shown, in an E2 reaction? (Sec. 7.8-7.9)
24. Which statements are true for an E1 reaction? (Sec. 7.9)
I) The rate limiting step of the reaction involves only the alkyl halide.
II) The rate limiting step of the reaction involves the alkyl halide and the base.
III) There is an intermediate carbocation.
IV) The order of reactivity is 1°>2°>3°.
a) I, III
b) II
c) I, III, IV
d) II, IV
25. Which conditions are best for preparing isopropyl methyl ether? (Sec. 7.10)
CH2
Cl CH3
CH3
Cl
CH2Cl
CH3
Cl
a) b) c) d)
d)
c)
b)
a)
acid
catalysis
heat
+
+
+
+
CHOH
H3C
H3C
CHBr
H3C
H3C
CH3Br
CHBr
H3C
H3C
CH3OH
CH3OH
Na OCH
CH3
CH3
Na OCH3
Chapter 7 Haloalkanes
83
Fill in the Blank
1. The major product of the following reaction is,
Cl H
KSCH3
DMSO (Sec. 7.6)
2. The major product of the following reaction is,
Br H
KOH
H2O (Sec. 7.6)
3. The major product of the following reaction is,
H I
NH3
(Sec. 7.6)
4. The major product of the following reaction is,
INaOCH2CH3
CH3CH2OH (Sec. 7.9)
5. The major product of the following reaction is,
H Br
H2O
(Sec. 7.6)
6. The reagent needed to complete the following reaction is,
Cl (Sec. 7.9)
Chapter 7 Haloalkanes
84
7. The reagent needed to complete the following reaction is,
BrH OHH
(racemic)
(Sec. 7.6)
8. The reagent needed to complete the following reaction is,
HBrHH3CO H OCH3
+
(Sec. 7.6)
9. The starting material needed to complete the following reaction is,
IKI
CH3CH2OH (Sec. 7.6)
10. The starting material needed to complete the following reaction is,
SH H
NaSH
acetone (Sec. 7.6)
True-False
1. Polar aprotic solvents favor SN1 reactions. (Sec. 7.6)
2. The order of SN1 reactivity of the following alkyl halides are listed in decreasing order. (Sec. 7.6)
Cl CH3 Cl Cl Cl> > >
3. The order of SN2 reactivity of the following alkyl halides are listed in decreasing order. (Sec. 7.6)
ClFIBr > > >
Chapter 7 Haloalkanes
85
4. The following nucleophiles are listed in decreasing order of reactivity in an SN2 reaction. (Sec. 7.6)
> > >I- Cl-Br- F-
5. The following nucleophiles are listed in decreasing order of reactivity in an SN2 reaction. (Sec. 7.6)
> >HO-F- H2N-
6. The name of the following compound is cis- (1R,2S)-1-chloro-2-bromocyclohexane. (Sec. 7.2)
ClBr
7. The name of the following compound is R, E - 4-bromo-2-pentene. (Sec. 7.2)
Br
8. The major product of the reaction of R-2-bromobutane with sodium iodide in acetone is S-2-iodobutane.
(Sec. 7.6)
9. The major product of the reaction of R-2-bromobutane with water is a racemic alcohol. (Sec. 7.6)
10. The major product of the reaction of bromocyclohexane and potassium t-butoxide in water is an ether.
(Sec. 7.6)
Chapter 7 Haloalkanes
86
Answers
Multiple Choice
1. c
2. a
3. c
4. b
5. a
6. b
7. c
8. b
9. c
10. a
11. d
12. d
13. b
14. a
15. c
16. a
17. b
18. c
19. b
20. a
21. b
22. c
23. c
24. a
25. b
Fill in the Blank
1.
H SCH3
2.
OHH
3.
HNH2
Chapter 7 Haloalkanes
87
4.
5.
OH HH OH
+
6. base
7. H2O
8. HOCH3
9.
Br Clor
10.
H Cl
(or –Br, -I)
True-False
1. F
2. F
3. F
4. T
5. F
6. F
7. T
8. T
9. T
10. F
Chapter 8 Alcohols, Ethers, and Thiols
88
Multiple Choice 1. Which is the IUPAC name for the following structure? (Sec. 8.2)
a) cyclohexenol b) 3-cyclohexen-1-ol c) 1-cyclohexen-4-ol d) 4-cyclohexenol
2. Which structures have the correct IUPAC name? (Sec. 8.2)
OCH2O
CH2OH
C
CH3H OCH3
CH3CH
CH3
OCH3
OH
OH
cis-1,2-dimethoxycyclohexane I
R-2-methoxy-1-propanol II
2-methoxypropane III
trans-1,3-cyclohexanediol IV
a) I, II b) III, IV c) II, III d) I, IV
3. Arrange the compounds in the order of increasing solubility in water (least first). (Sec. 8.4)
a) I, III, II, IV b) III, I, IV, II c) I, IV, II, III d) IV, I, III, II
OH
IVIII
III
CH3CH2CH2CH2CH2OHCH3OCH2CH2OCH3
CH3OCH3CH3CH2CH2CH2OCH3
Chapter 8 Alcohols, Ethers, and Thiols
89
4. Which are secondary alcohols? (Sec. 8.2)
a) I, III b) II, III c) III, IV d) I, IV
5. Arrange the compounds in the order of increasing acidity (least first). (Sec. 8.3)
a) III, I, II, IV b) I, III, IV, II c) II, III, I, IV d) II, I, III, IV
6. Arrange the compounds in the order of increasing acidity (least first). (Sec. 8.6)
a) II, I, III, IV b) I, IV, II, III c) III, II, I, IV d) II, I, IV, III
CH3
OHCH3C
CH3
CH3
OH C CH3C
H
H
CHCH3
OH
H OH
I II III IV
IVIIIIII
H2OCH3CHCH3
OHCH3COH
CH3
CH3CH3CH2OH
IVIIIIII
H2OH2SCH3CH2SHCHOHH3C
H3C
Chapter 8 Alcohols, Ethers, and Thiols
90
7. Arrange the compounds in the order of increasing boiling point (lowest first). (Sec. 8.3, 8.4, 8.6)
a) II, I, III, IV b) I, IV, II, III c) IV, I, III, II d) I, IV, III, II
8. Arrange the compounds in the order of increasing solubility in water (lowest first). (Sec. 8.2)
CH3OH CH3CH2CH2CH2CH2OH
CH3CH2CH2CH2OH HOCH2CH2CH2CH2CH2OH
I II
III IV
a) IV, III, II, I b) II, III, IV, I c) III, IV, II, I d) II, IV, III, I
9. Which alcohol will form the most stable carbocation? (Sec. 8.3)
IVIIIIII
CH3CH2SHCH3CH2OHH2OH3CO
CH3
d)
c)
b)
a)
CH3OH
OH
COH
CH3
CH3
CH3
CH3CHCH2OH
CH3
Chapter 8 Alcohols, Ethers, and Thiols
91
10. How many isomers, including stereoisomers, can be formed from the hydroxylation of 4-methylcyclohexene using osmium tetroxide? (Sec. 8.3, 8.4)
a) 2 b) 4 c) 6 d) 8
11. Arrange the following in order of increasing ability to hydrogen bond (lowest first). (Sec. 8.3, 8.4, 8.6)
a) I, II, III, IV b) III, I, IV, II c) II, IV, I, III d) I, IV, II, III
12. Which reagents do not effect the following conversion? (Sec. 8.3)
a) I, II b) II, III c) II, IV d) I, III
13. Which is the major product from the acid catalyzed hydrolysis of cyclohexene oxide? (Sec. 8.5)
HO CH3 Cl CH3
HCl Cl2 SOCl2 NaCl
I. II. III. IV.
H H
HO OH
OH
OH
H
H
O
a) b)
c) d)
HO HCH3O H
CH3S HCH3 HI. II.
III. IV.
Chapter 8 Alcohols, Ethers, and Thiols
92
14. Which is the major product of the following reaction? (Sec. 8.5)
C CO
H
H
H
HH2NCH2CH2NH2+2
HOCH2CH2NH2 O N
HOCH2CH2NHCH2CH2OH HOCH2CH2NHCH2CH2NHCH2CH2OH
a) b)
c) d)
15. Which is the best method for making the following conversion? (Sec. 8.3)
16. Which is the product of the following reaction? (Sec. 8.3, 8.5)
H3PO4
H2SO4
Pt / H2
H2SO4
PCC H3PO4COO H
O
heatdilute dilute
heat
a) b)
c) d)
OHH3PO4 OsO4 / ROOH
heat
CH3CHCH3
OHCH3CH2CH2OH
d)c)
b)a)
O
H
H
O
O
OH
OH
OH
Chapter 8 Alcohols, Ethers, and Thiols
93
17. Which is the product of the following reaction? (Sec. 8.3)
18. Treatment of cyclopentene with dilute sulfuric acid, followed by reaction with chromic acid gives which of the following compounds as the major product? (Sec. 8.3)
19. Which is the major product of the following reaction? (Sec. 8.3, 8.5)
20. Which are the best conditions for the preparation of 1-chloro-2-methylpropane starting from 2-methyl-1-propanol? (Sec. 8.3)
CH2OHPCC
O
a) b) c) d)
O
HH3CCCH2CH2CH2CH
O O C
O
OH
OOH
OH O
O
Oa) b) c) d)
H3PO4
heatHCl SOCl2
K Cl2 NaCl
a) b)
c) d)
heat
Pt / H2H3PO4CH3CHCH2OH
CH3
d)c)
b)a)
CH3CH2CH2CH3CH3CHCH3
CH3
CH3CHCOH
CH3
O
CH3CHCH
CH3
O
Chapter 8 Alcohols, Ethers, and Thiols
94
21. Which is the major product of the following reaction? (Sec. 8.5)
22. Which is the major product of the following reaction? (Sec. 8.3, 8.5)
23. Arrange the following in order of increasing rate of reactivity with HBr (least first). (Sec. 8.3)
a) I, II, IV, III b) II, I, III, IV c) IV, III, I, II d) III, II, IV, I
24. Classify the following reaction. (Sec. 8.6)
a) oxidation b) reduction c) neither d) both
H3CCOOH
O
CH2Cl2
HO OHCH3 OH3C CH2HO OH3C
a) b) c) d)
C CO
H H
H H+ / H2O CrO3H2SO4
C COH
O O
C CH2OH
O
CH COH
OOHC CH
O Oa) b) c) d)
IVIIIIII
CH3OH
CH2OHOH
CH3
OH
2 CH3CH2SHCH3CH2S SCH2CH3
Chapter 8 Alcohols, Ethers, and Thiols
95
25. Which is the major product of the following reaction? (Sec. 8.5)
a) 3-pentanol b) 2-pentanol c) 2-methyl-2,3-pentanediol d) 4-methyl-3,4-pentanediol
Fill in the Blank 1. The major product of the following reaction is,
OH H2SO4
heat (Sec. 8.3)
2. The major product of the following reaction is,
OH
H2CrO4
acetoneH2O (Sec. 8.3)
3. The major product of the following reaction is,
OHNa
(Sec. 8.3) 4. The major product of the following reaction is,
OH2NCH3
(Sec. 8.5) 5. The reagent needed to complete the following reaction is,
OH O (Sec. 8.3)
C CHO
CH2CH3H3C
H3C
H+ / H2O
Chapter 8 Alcohols, Ethers, and Thiols
96
6. The reagent needed to complete the following reaction is,
OH Cl (Sec. 8.3)
7. The reagent needed to complete the following reaction is,
O
(Sec. 8.5) 8. The starting material needed to complete the following reaction is,
H3PO4
heat (Sec. 8.3)
9. The starting material needed to complete the following reaction is,
Cl
SOCl2
(Sec. 8.3) 10. The reaction arrows (curved arrows) required to complete the following reaction mechanisms are,
OHH SO4H
O+
HH
C+
HH
H H
SO4H-
(Sec. 8.3)
Chapter 8 Alcohols, Ethers, and Thiols
97
True-False 1. The strongest acid in the following list is water. (Sec. 8.3, 8.4, 8.6)
CH3
OCH3 CH3
SCH3 H
OH CH3
OH CH3
SH
2. The major product of the reaction of 1-propanol with PCC is propanoic acid. (Sec. 8.3) 3. The product of the reaction of methanol with sodium metal is sodium methoxide. (Sec. 8.3) 4. The major product of the reaction of 3-methyl-2-butanol with hot, concentrated sulfuric acid is 3-methyl-1-butene. (Sec. 8.3) 5. The following compound is named 1-chloro-2,2-dimethyl-4-pentanol. (Sec. 8.2)
ClOH
6. The following compound is named 2,6-dimethyl-1,4-cyclohexanediol. (Sec. 8.2)
OH
OH 7. The following compounds are listed in decreasing boiling point order (highest first). (Sec. 8.2)
CH3CH2
OHCH3
OH CH3CH2CH2
OH CH3CH2CH2CH2
OH> > >
8. The following compounds are listed in decreasing boiling point order (highest first). (Sec. 8.2, 8.4)
CH3
OCH3 H
OHCH3
OH> >
9. The following compounds are listed in decreasing order of solubility in water (highest first). (Sec. 8.2)
CH3CH2
OH CH3
OHCH3CH2CH2
OHCH3CH2CH2CH2
OH > > >
10. The following compounds are listed in increasing order of solubility in water (lowest first). (Sec. 8.2, 8.4)
OH O< <
Chapter 8 Alcohols, Ethers, and Thiols
98
Answers Multiple Choice 1. b 2. b 3. c 4. c 5. c 6. b 7. d 8. b 9. b 10. a 11. a 12. c 13. b 14. d 15. a 16. a 17. b 18. c 19. c 20. b 21. d 22. a 23. c 24. b 25. c Fill in the Blank 1.
2.
O
OH
3.
O Na+
4.
OH
NHCH3 5. PCC
Chapter 8 Alcohols, Ethers, and Thiols
99
6. SOCl2 7. a peracid 8.
OH
9.
OH 10.
OHH SO4H
O+
HH
C+
HH
H H
SO4H-
True-False 1. F 2. F 3. T 4. F 5. F 6. T 7. F 8. F 9. F 10. F
Chapter 9 Benzene and Its Derivatives
100
Multiple Choice 1. Which structures have the correct IUPAC names? (Sec. 9.4)
a) I, II b) III, IV c) I, IV d) II, III
CH3
Br
CH3
Cl
Br
NO2
Cl
OCH3
CH2CH3
I. 2-bromotoluene II. para methyl, meta chloro bromobenzene
III. meta chloroaniline IV. para ethylanisole
Chapter 9 Benzene and Its Derivatives
101
2. Which of the named compounds have correct structures? (Sec. 9.4)
CH3
Cl CH2CH2Br
O OH
Br
OCH3
NO2
NH2
ClCl
Cl
I. meta chlorotoluene II. bromomethyltoluene III. para bromophenol
IV. ortho nitroanisole V. 2,4,6-trichloroaniline
a) I, II, IV b) I, III, IV c) I, IV, V d) II, III, V
3. How many Kekule structures are possible for naphthalene? (Sec. 9.2, 9.3)
a) 3 b) 4 c) 5 d) 6
4. How many S-orbital electrons are in the following molecule? (Sec. 9.3)
a) 4 b) 6 c) 8 d) 10
N
N
H
Chapter 9 Benzene and Its Derivatives
102
5. Which structures are aromatic? (Sec. 9.3)
a) II, III b) III, IV c) I, III d) II, IV
6. Arrange the compounds in order of increasing acidity (least first). (Sec. 9.9)
a) I, II, III, IV b) III, II, IV, I c) I, IV, III, II d) II, III, IV, I
7. Arrange the compounds in order of increasing acidity (least first). (Sec. 9.9)
OH OHO OH
OCH3
I II III IV
a) I, II, III, IV b) III, I, II, IV c) IV, II, I, III d) IV, II, III, I
OCH2
N O
O
I II III IV
IVIIIIII
OH
NO2
NO2
OH
NO2
OH
Cl
OH
Chapter 9 Benzene and Its Derivatives
103
8. Arrange the compounds in order of increasing acidity (least first). (Sec. 9.9, 2.4)
a) I, II, III, IV b) III, IV, II, I c) I, II, IV, III d) II, I, III, IV
9. How can phenol be distinguished from cyclohexanol? (Sec. 9.9, 8.3)
a) solubility in water b) solubility in hydrochloric acid solution c) solubility in sodium bicarbonate solution d) solubility in sodium hydroxide solution
10. How many mono-bromoanthracenes are possible? (Sec. 9.2, 9.3)
a) 1 b) 2 c) 3 d) 4
11. Which contributing resonance structure is the most important for the bromination of anisole? (Sec. 9.8)
12. Which is the electrophile in the nitration of benzene? (Sec. 9.7)
OCH3
H Br
OCH3
BrH
OCH3
BrH
OCH3
BrH
a) b) c) d)
HNO3 NO2 NO3 NOa) b) c) d)
IVIIIIII
CH3COH
OH2CO3
OHOH
Chapter 9 Benzene and Its Derivatives
104
13. Which compound reacts most readily in the nitration reaction? (Sec. 9.7)
14. Arrange the compounds in order of increasing reactivity toward electrophilic aromatic substitution (lowest first). (Sec. 9.7)
a) II, I, IV, III b) I, III, IV, II c) III, I, IV, II d) IV, III, II, I
15. Arrange the compounds in order of increasing reactivity toward electrophilic aromatic substitution (lowest first). (Sec. 9.7)
CH3 Cl OHO
I II III IV
a) III, II, I, IV b) IV, II, I, III c) III, I, II, IV d) I, II, III, IV
CH3
HNCCH3
O
CH3
OCH3
CH3
COH
O
CH3
SO3H
a) b) c) d)
CNHCH3
O
NH2 NO2 HNCCH3
O
I II III IV
Chapter 9 Benzene and Its Derivatives
105
16. Which is the major product of the following reaction? (Sec. 9.6)
17. Which is the major product of the following reaction? (Sec. 9.6, 9.8)
OCH3
NO2 H3CCCl
O
AlCl3
OCH2CCH3
O
NO2
OCH3
NO2
H3CCO
OCH3
NO2
CCH3O
OCH3
NO2
CCH3
O
a) b) c) d)
d)c)
b)a)
CH2
HCO
Br
CH2
HCO
Br
CH2
HCO
Br
CH2
HCO
Br
FeBr3
Br2CH2
HCO
Chapter 9 Benzene and Its Derivatives
106
18. Which is the major product of the following series of reactions? (Sec. 9.5, 9.8)
19. Which is the best reaction sequence for preparing the following compound from benzene? (Sec. 9.6, 9.8)
CH3
AlCl3
H3CCCl
O
K2Cr2O7
H2SO4
COH
O
COH
O
CCH3
O
COH
O
CCH3
O
CCH3
O
OCH3
COH
O
a) b) c) d)
COH
O
NO2
AlCl3CH3Cl
K2Cr2O7H2SO4
HNO3H2SO4
HNO3H2SO4
K2Cr2O7H2SO4
AlCl3CH3Cl
AlCl3CH3Cl
HNO3H2SO4
K2Cr2O7H2SO4
AlCl3H3CCl
O
HNO3H2SO4
a)
b)
c)
d)
Chapter 9 Benzene and Its Derivatives
107
20. Which is the major product of the following reaction? (Sec. 9.6, 9.8)
21. Which is the electrophile in the final reaction step for the following reaction? (Sec. 9.7)
22. Which is the major product of the following reaction? (Sec. 9.6, 9.8)
a) 1-chloro-4-nitrobenzene b) 1-chloro-3-nitrobenzene c) 1-chloro-2-nitrobenzene d) a mixture of 1-chloro-4-nitrobenzene and 1-chloro-2-nitrobenzene
CCH2CH2CCl
O O
AlCl3
O
O O
O
a) b)
c) d)
OH H3CCCH3
OC
CH3
CH3
HO OHH3PO4
+
HO CCH3
CH3
C
CH3
HO OH
HO C
O
H3CCCH3
OH
a) b)
c) d)
HNO3H2SO4
Cl2FeCl3
Chapter 9 Benzene and Its Derivatives
108
23. Which is the major product of the following reactions? (Sec. 9.6, 9.8)
24. Which is the major product of the following reactions? (Sec. 9.5, 9.6, 9.8)
a) para chlorobenzoic acid b) meta chlorobenzoic acid c) a mixture of para and meta chlorobenzoic acid d) a mixture of ortho and para chlorobenzoic acid
25. Which is the electrophile in the following reaction? (Sec. 9.7)
CH2HNO3H2SO4
Br2FeBr3
CH2
Br NO2
CH2
Br
NO2
CH2Br NO2 CH2Br
NO2
a) b)
c) d)
Cl2FeCl3
CH3ClFeCl3
K2Cr2O7H2SO4
+ H3PO4
HPO3a) b) c) d)
Chapter 9 Benzene and Its Derivatives
109
Fill in the Blank 1. The major product of the following reaction is,
OH
H3PO4
(Sec. 9.6, 9.8) 2. The major product of the following reaction is,
K2Cr2O7
H2SO4
(Sec. 9.5) 3. The major product of the following reaction is,
Br O
Cl
AlCl3 (Sec. 9.6, 9.8)
4. The major products of the following reaction are,
OH OH
NaOH
H2O+
(Sec. 9.9)
Chapter 9 Benzene and Its Derivatives
110
5. The major products of the following reaction are, O OH
OH
+NaHCO3
H2O (Sec. 9.9)
6. The reagent that completes the following reaction is,
CH3 CH3
NO2 (Sec. 9.6, 9.8) 7. The reagents that complete the following reactions are,
SO3H (Sec. 9.6, 9.8) 8. The starting material and reagent that complete the following reaction are,
SO3H
Cl (Sec. 9.6, 9.8)
Chapter 9 Benzene and Its Derivatives
111
9. The reagents and mid-reaction product that complete the following scheme are,
Cl
O (Sec. 9.6, 9.8) 10. The reaction arrows (curved arrows) required to complete the following reaction mechanisms are,
Br+
C+ BrH
HBr
(Sec. 9.7) True-False 1. The name of the following structure is 2,4-diethylnitrobenzene. (Sec. 9.4)
NO2
2. The name of the following structure is 3,5-dibromobenzoic acid. (Sec. 9.4)
O OH
BrBr 3. The product of the reaction of toluene with concentrated nitric and sulfuric acid is m-nitrotoluene. (Sec. 9.6, 9.8) 4. The product of the reaction of isopropylbenzene with chromic acid is methylphenyl ketone. (Sec. 9.5) 5. The product of the reaction of benzoic acid and chlorine/AlCl3 is m-chlorobenzoic acid. (Sec. 9.6, 9.8)
Chapter 9 Benzene and Its Derivatives
112
6. The following compound is aromatic. (Sec. 9.3)
7. The following reaction scheme will synthesize the product shown. (Sec. 9.5, 9.6, 9.8)
Br
O OH
CH3CH2Cl
AlCl3
K2Cr2O7
H2SO4
Br2
FeBr3
8. The following reaction scheme will synthesize the product shown. (Sec. 9.6, 9.8)
SO3H
CH3CH2Cl
AlCl3H2SO4
SO3
9. The following compounds are listed in decreasing order of reactivity toward electrophilic aromatic substitution. (Sec. 9.7)
OH CH3 SO3H
> > >
10. The following compounds are listed in decreasing order of reactivity toward electrophilic aromatic substitution. (Sec. 9.7)
Cl NO2O
> > >
Chapter 9 Benzene and Its Derivatives
113
Answers Multiple Choice 1. c 2. c 3. a 4. b 5. c 6. a 7. c 8. a 9. d 10. c 11. d 12. b 13. b 14. c 15. b 16. b 17. c 18. b 19. d 20. d 21. a 22. b 23. c 24. d 25. b Fill in the Blank 1.
2.
OHO
Chapter 9 Benzene and Its Derivatives
114
3.
Br
O 4.
O OH
+
5.
OOOH
+
6. HNO3, H2SO4 7.
ClAlCl3
SO3, H2SO4
8.
Cl
SO3 , H2SO4
Chapter 9 Benzene and Its Derivatives
115
9.
Cl
O
O
AlCl3 Cl2 , FeCl3
10.
Br+
C+ BrH
HBr
True-False 1. T 2. T 3. F 4. F 5. T 6. F 7. F 8. T 9. T 10. F
Chapter 10 Amines
116
Multiple Choice 1. Which is the correct structure for diphenylamine? (Sec. 10.3)
2. Which is the IUPAC name for the following structure? (Sec. 10.3)
a) N-methyl-tert-butylamine b) N-methyl-1,1-dimethylethylamine c) N-methyl-2-methyl-2-propanamine d) tert-butyl methyl amine
3. Which is the structure for N,N-dimethyl-3-hexanamine? (Sec. 10.3)
NH2
N
H
NH2
CH2
NH2
a) b)
c) d)
N
H
C CH3
CH3
CH3
H3C
d)c)
b)a)
CH3CH2CHCH2CH2CH3
N
CH3
CH3
CH3CH2CCH2CH2CH2NH2
CH3
CH3
CH3CH2CH2CCH2CH3
NHCH3
NHCH3
CH3NCH2CH2CH2CH3
CH3
Chapter 10 Amines
117
4. Which pairs of names and structures match correctly? (Sec. 10.3)
a) I and D, II and B b) III and A, IV and E c) V and C, III and B d) III and D, IV and E
5. Which structures are secondary amines? (Sec. 10.2)
a) I, II b) II, III c) III, IV d) II, IV
NH
NH
NH2
NH
N
I. piperidine A.
II. pyrrolidine B.
III. pyrrole C.
IV. pyridine D.
V. cyclohexylamine E.
CH3CHCH2NH2
CH3NCH3
H
NH2 NH
I II
III IV
Chapter 10 Amines
118
6. Which is the classification of the following amine? (Sec. 10.2)
a) 1° b) 2° c) 3° d) 4°
7. Which is the name for the following compound? (Sec. 10.3)
a) phenylammonium chloride b) phenyltrihydrogenammonium chloride c) aniline chloride d) benzylammonium chloride
8. Which is the name for the following compound? (Sec. 10.3)
a) 4-carboxy aniline b) 1-amino-4-carboxybenzene c) benzylamine carboxylic acid d) 4-aminobenzoic acid
9. Which compound is the strongest base? (Sec. 10.5)
N
CH3
CH3H3CCH2CH2CH2 Cl
NH3 Cl
H2N COH
O
d)c)b)a) CH3NH3 OHCH3NCH3
CH3
CH3NH
CH3
CH3NH2
Chapter 10 Amines
119
10. Which compound is the strongest base? (Sec. 10.5)
11. Which reactions will proceed predominately to products as written? (Sec. 10.6)
a) I, II b) III, IV c) II, IV d) I, III
12. When the following compounds are dissolved in water at the same concentrations, which one will have the lowest pH (i.e., most acidic)? (Sec. 10.5)
NH2 NH2
Br
NH2
NO2
NH2
CH3
a) b) c) d)
b)
d)c)
a)
CH2NCH3 Cl
CH3
CH3
CH2NCH3 Cl
CH3
H
CH2NCH3 OH
CH3
CH3
CH2NCH3
CH3
CH3NH2 H2O CH3NH3 OH
CH3COH
OCH3CO
O
CH3NCH3
CH3
CH3NCH3
CH3
H
NH3 NH2
CH3NH2
CH3NH2
CH3NH2
CH3NH3
CH3NH3
CH3NH
+
+
+
+
+
+
+
+
I.
II.
III.
IV.
Chapter 10 Amines
120
13. Arrange the amines in order of increasing basicity (weakest first). (Sec. 10.5)
a) IV, II, III, I b) II, I, III, IV c) I, II, III, IV d) II, I, IV, III
14. At pH 5.0, the ratio of morpholine and morpholinium ion is 1:1622. Which is the pKb of morpholine? (Sec. 10.5)
a) 3.21 b) 5.79 c) 8.21 d) 9.25
15. Guanidine has a pKb value of 0.4. Which is the ratio of guanidine to its conjugate acid at blood pH of 7.4? (Sec. 10.5)
a) 10-6.2:1 b) 10+6.2:1 c) 1:1 d) 2.5:1
16. Which are the correct positions for the site of protonation of the bases, guanidine and imidazole? (Sec. 10.6)
a) I, III b) II, IV c) I, IV d) II, III
NH2 NH2
CH3
NH2
N
H
I II III IV
C
NH
NH2H2NN
N
H
I
II
III
IV
Chapter 10 Amines
121
17. Arrange the amines in order of increasing boiling point (lowest first). (Sec. 10.4)
a) II, III, I, IV b) III, I, IV, II c) IV, II, III, I d) IV, III, I, II
18. Arrange the amines in order of increasing boiling point (lowest first). (Sec. 10.4) methylamine ethylamine propylamine cyclohexylamine I II III IV
a) IV, III, II, I b) I, II, III, IV c) III, II, I, IV d) II, I, IV, III
19. Arrange the amines in order of increasing solubility in water (least first). (Sec. 10.4)
a) II, III, I, IV b) IV, II, III, I c) IV, III, II, I d) I, III, II, IV
20. Arrange the amines in order of increasing solubility in water (least first). (Sec. 10.4) ethylamine methylamine propylamine cyclohexylamine I II III IV
a) II, I, III, IV b) IV, II, III, I c) IV, III, I, II d) I, III, II, IV
IVIIIIII
N
CH2CH3
CH2CH3CH3CH2 CH3CH2NH2 CH3CH2NH
CH2CH3
CH3CH2NH3 Cl
IVIIIIII
N
CH2CH3
CH2CH3CH3CH2 CH3CH2NH2 CH3CH2NH
CH2CH3
CH3CH2NH3 Cl
Chapter 10 Amines
122
21. Arrange the following in order of increasing strength of the hydrogen bonds (weakest first). (Sec. 10.4)
a) I, II, III, IV b) II, I, IV, III c) II, IV, I, III d) I, IV, II, III
22. Which is the product of the following reaction? (Sec. 10.7)
NO2
CH3CH3
Fe, HCl
ethanol/water
CH3CH3
NH3Cl
CH3CH3
NO2
COOHHOOC
NO2
CH3CH3
ClCl
a) b)
c) d)
H2NH OH2 H3N HNH2
H2O HOH H3N HOH
I. II.
III. IV.
Chapter 10 Amines
123
23. Which is the product of the following reaction? (Sec. 10.8)
NH2
CH3
NaNO2
HCl, 0° C
CH3
NH2
CH3
NO2O2N
CH3
N+
N
NH2
CH3
NO2O2N
Cl-
a) b) c) d)
24. Which is the product of the following reaction? (Sec. 10.8)
NH2
CH3
NaNO2
HCl, 0° C
H3PO2
NH3Cl
CH3
NH2
CH3
PO2O2P
CH3
NH2
a) b) c) d)
Chapter 10 Amines
124
25. The following mixture was extracted with 1 M HCl, followed by 1 M NaOH, followed by ether. Which compound is recovered from the acid solution? (Sec. 10.6)
a) I b) II c) III d) None of the above
Fill in the Blank 1. The name of the following compound is _______________________________. (Sec. 10.3)
CH3
NH
CH3
2. The name of the following compound is ______________________________. (Sec. 10.3)
NH
Br
3. The name of the following compound is _________________________________. (Sec. 10.3)
N+
N
CH3
Cl-
NH3C CH3
OH CHH3C CH3
I II III
Chapter 10 Amines
125
4. The starting material needed to complete the following reaction is,
NH2
BrBr
Fe, HCl
(Sec. 10.7 5. The starting material needed to complete the following reaction is,
CH3
CH3
CH3H3PO2
(Sec. 10.8) 6. The reactants needed to complete the following reaction are,
NH2 OH
(Sec. 10.8) 7. The major product of the following reaction is,
NH2
O
OH
1) NaNO2, HCl, H2O, 0° C
2) warm solution
(Sec. 10.8)
Chapter 10 Amines
126
8. The order of decreasing basicity of the following amines is (1 is the most basic),
O2N NH2 N N
CH3
CH3 CH3
NH2CH3
(Sec. 10.5) 9. The order of increasing basicity of the following compounds is (1 is the least basic),
CH3 OH NH2O OH
(Sec. 10.5) 10. The order of increasing boiling point of the following compounds is (1 is lowest boiling),
CH3 OH NH2O OH
(Sec. 10.5) True-False 1. The name of the following compound is N-cyclopentylethanamine. (Sec. 10.3)
NCH2CH3H
Chapter 10 Amines
127
2. The name of the following compound is 3,5-dimethylpiperidine. (Sec. 10.3)
N
CH3CH3
H
3. The strongest base in the following group is aniline. (Sec. 10.5)
NH2 NH2
N
4. The strongest base in the following group is methylthiocyclohexane. (Sec. 10.5)
NHCH3 O
CH3S
CH3
5. Cyclohexanamine is a 2º amine. (Sec. 10.2) 6. tert-butyl methyl amine is a 3º amine. (Sec. 10.2) 7. The pKa for ethyl ammonium ion is 10.8 (ethyl amine pKb is 3.2). (Sec. 10.5) 8. Tertiary amines are generally stronger bases than secondary amines. (Sec. 10.5) 9. The equilibrium for the reaction of p-nitroaniline and acetic acid lies to the right. (Sec. 10.6) 10. The reaction of aniline with nitrous acid after warming yields phenol. (Sec. 10.8)
Chapter 10 Amines
128
Answers Multiple Choice 1. b 2. c 3. d 4. d 5. d 6. d 7. a 8. d 9. b 10. d 11. c 12. c 13. c 14. b 15. a 16. c 17. a 18. b 19. d 20. c 21. b 22. b 23. c 24. c 25. a Fill in the Blank 1. N-methyl 2-methylcyclohexanamine 2. 3-bromopiperidine 3. 3-methylbenzene diazonium chloride 4.
NO2
BrBr
Chapter 10 Amines
129
5.
N+
N
Cl-
6.
1) NaNO2, H2O, HCl, O°
2) warm 7.
OH
OH
O 8. 4, 3, 2, 1 9. 1, 3, 4, 2 10. 1, 3, 2, 4 True-False 1. F 2. T 3. F 4. F 5. F 6. F 7. T 8. F 9. F 10. T
Chapter 11 Infrared Spectroscopy
130
Multiple Choice 1. Which is the approximate energy range for absorptions in the infrared region of the electromagnetic spectrum? (Sec. 11.4)
a) 50 to 100 kcal/mol b) 10 to 50 kcal/mol c) 1 to 10 kcal/mol d) 0.01 to 0.1 kcal/mol
2. Which is the wave number for an infrared band at 5 microns (Pm)? (Sec. 11.2)
a) 500 cm-1 b) 2000 cm-1 c) 5000 cm-1 d) 10,000 cm-1
3. Which is the wavelength (Pm) of an infrared absorption band at 500 cm-1? (Sec. 11.2)
a) 0.2 b) 2.0 c) 20 d) 25
4. Which is the order of increasing bond stretching frequency (lowest first)? (Sec. 11.4)
I) C=N II) C=O III) C=C IV) C=S
a) II, I, IV, III b) I, II, IV, III c) III, I, II, IV d) IV, III, I, II
5. Which is the order of increasing bond stretching frequency (lowest first)? (Sec. 11.4)
I) C-H II) N-H III) O-H IV) F-H
a) I, II, III, IV b) I, III, II, IV c) IV, III, II, I d) III, II, I, IV
6. The broadening of the stretching vibration peak for alcohols is mainly due to which of the following? (Sec. 11.5)
a) water contamination b) a strong dipole moment c) hydrogen bonding d) coupling peaks
Chapter 11 Infrared Spectroscopy
131
7. A compound has the molecular formula C5H10O, and strong absorptions at 1100 and 3350 cm-1. Which is the most likely structure for the compound? (Sec. 11.5)
8. Which compound has a sharp IR absorption at 1710 cm-1 and a broad band at 3300 cm-1? (Sec. 11.5)
9. Which compound has an IR absorption at 3300 cm-1 but no band at 1710 cm-1? (Sec. 11.5)
10. Which is the most likely structure for a compound with molecular formula C5H8O, and an IR spectrum with a peak at 1710 cm-1 but no peak at 1650 cm-1? (Sec. 11.5)
O
CH3CH2CCH2CH3
O
OH C C
H
H3C H
CH2OCH3
a) b)
c) d)
CH3COH
O
CH3CH2OH CH3CCH3
O
CH3OCH3a) b) c) d)
CH3COH
O
CH3CH2OH CH3CCH3
O
CH3OCH3a) b) c) d)
O OH
OC C
H3C
H
H
CH2CH
O
a) b)
c) d)
Chapter 11 Infrared Spectroscopy
132
11. Which compound has characteristic IR peaks at 3100 cm-1, 1600 cm-1, and 1480 cm-1? (Sec. 11.5)
12. Which compound has characteristic IR peaks at 3100 cm-1 and 1650 cm-1, but not 1480 cm-1? (Sec. 11.5)
13. Which compound has a characteristic IR peak at 2900 cm-1? (Sec. 11.5)
a) I, II, III b) I, II, III, IV c) III, IV d) I, III, IV
d)c)
b)a)
CCH2CH3
CH3
CH3
H3CCH3CH2CH2OCH2CH3
C C
H3C
H
H
CH CH3
CH3
CH3
d)c)
b)a)
CCH2CH3
CH3
CH3
H3CCH3CH2CH2OCH2CH3
C C
H3C
H
H
CH CH3
CH3
CH3
IV.III.
II.I.
CCH2CH3
CH3
CH3
H3CCH3CH2CH2OCH2CH3
C C
H3C
H
H
CH CH3
CH3
CH3
Chapter 11 Infrared Spectroscopy
133
14. Which compounds will have a particularly weak characteristic IR stretching frequency? (Sec. 11.5)
a) I, II b) III, IV c) I, III d) II, IV
15. A compound has a molecular formula, C5H10O and no peaks in the IR spectrum at 3300 cm-1or 1680-1750 cm-1. Which could be this compound? (Sec. 11.5)
a) I, II b) III, IV c) II, III d) II, IV
16. A compound has a molecular formula C7H14O2 and a broad signal in the region of 2850-3000 cm-1 and a signal in the region of 1710-1780 cm-1 in the IR spectrum. Which could be the compound? (Sec. 11.5)
OH CH3CHC
OCH3
CH2
H
CH3CCH2CH2CH3
O
O
I II III IV
CH3CH2CH2COCH
OCH3
CH3 O OCH2CH3
CH3CH2CH2CH2CH2CH2COH
O
COH
O
a) b)
c) d)
IVIII
III
CH3CH2C CH2H2C CCH3
CH3
H3CC CCH3C CCH3
CH3
H3C
H3C
Chapter 11 Infrared Spectroscopy
134
17. A compound has a molecular formula of C5H9N and the IR spectrum has no peaks in the region of 3000-3500 cm-1. Which could be the compound? (Sec. 11.5)
18. Which region in the IR spectrum could be used to distinguish between butanoic acid and 2-butanone? (Sec. 11.5)
a) 3200-3600 cm-1 b) 1600 cm-1 c) 1680-1750 cm-1 d) 2500-3300 cm-1
19. Which region in the IR spectrum could be used to distinguish between benzyl amine and benzamide? (Sec. 11.5)
a) 1475 cm-1 and 1600 cm-1 b) 3030 cm-1 c) 3100-3500 cm-1 d) 1630-1690 cm-1
20. Which region in the IR spectrum could be used to distinguish between benzene and cyclohexane? (Sec. 11.5)
a) 3000 cm-1 b) 1600 cm-1 c) 1680-1750 cm-1 d) 3200-3600 cm-1
21. Very prominate peaks in the IR spectrum are sufficient to distinguish between which compounds? (Sec. 11.5)
I) butane and cyclobutane II) toluene and methylcyclohexane III) 2-pentanone and 3-pentanone IV) pentanal and 1-pentene
a) I, III b) II, III c) II, IV d) III, IV
CH3CCH2NH2
CH3
CH3
H2C CN
H
CH3
CH3
NH3C
CH2CH3
CH2CH3
NH
a) b)
c) d)
Chapter 11 Infrared Spectroscopy
135
22. Very prominate peaks in the IR spectrum are sufficient to distinguish between which compounds? (Sec. 11.5)
I) diethyl ether and diethylamine II) cyclohexanone and cyclopentanone III) pentanal and pentanol IV) 2-hexene and 3-hexene
a) I, III b) II, III c) II, IV d) III, IV
23. Very prominate peaks in the IR spectrum are sufficient to distinguish between which compounds? (Sec. 11.5)
I) butanoic acid and methyl butanoate II) dimethylamine and N,N-dimethylformamide III) triethylamine and dimethylpropanamine IV) 2-pentanol and 3-pentanol
a) I, II b) II, III c) I, IV d) III, IV
24. Which is the index of hydrogen deficiency for a compound having molecular formula C7H5Cl2NO? (Sec. 11.5)
a) 4 b) 5 c) 6 d) 7
25. Which is the index of hydrogen deficiency for a compound having molecular formula C12H13Br2NO2? (Sec. 11.5)
a) 5 b) 6 c) 7 d) 8
Fill in the Blank 1. The energy in kcal/mol of 606.06 Pm light is ___________________. (Sec. 11.2) 2. The energy in kcal/mol of 3350 cm-1 light is ___________________. (Sec. 11.2) 3. The _______________ cm-1 region would best distinguish between the following structures. (Sec. 11.5)
O
OH
O
Chapter 11 Infrared Spectroscopy
136
4. The ______________ cm-1 region would best distinguish between the following structures. (Sec. 11.5)
O
5. The ___________________functional group has a characteristic absorption in the 3200-3500 cm-1. (Sec. 11.5) 6. The ___________________functional group has a characteristic absorption in the 1630-1800 cm-1. (Sec. 11.5) 7. The index of hydrogen deficiency for the compound of formula C11H15NO is ______________. (Sec. 11.5) 8. The index of hydrogen deficiency for the compound of formula C8H10Br2O2 is ______________. (Sec. 11.5) 9. The _______________ cm-1 region is characteristic of the alkane stretch. (Sec. 11.5) 10. The _______________ cm-1 region is characteristic of the alkene stretch. (Sec. 11.5) True-False 1. The following molecule is not IR active. (Sec. 11.5)
H
2. The following molecule is not IR active. (Sec. 11.5)
3. 3-Hexanone has an IR absorption in the 3200-3500 cm-1 region. (Sec. 11.5) 4. 2-Pentenal has an IR absorption in the 1630-1800 and 1600-1680 cm-1 region. (Sec. 11.5) 5. The 3200-3500 cm-1 region can be used to distinguish between alcohols and amines by frequency alone. (Sec. 11.5) 6. The 1630-1800 cm-1 region can be used to distinguish between alcohols and carboxylic acids. (Sec. 11.5) 7. The strength of absorption signal in the 3200-3500 cm-1 region is greater for alcohols than amines. (Sec. 11.5) 8. The strength of absorption signal in the 1630-1680 cm-1 region is greater for carbonyl groups than alkene groups. (Sec. 11.5) 9. The index of hydrogen deficiency for C7H6Br4O2 is 3. (Sec. 11.5) 10. The index of hydrogen deficiency for C9H12N2O is 4. (Sec. 11.5)
Chapter 11 Infrared Spectroscopy
137
Answers Multiple Choice 1. c 2. b 3. c 4. d 5. a 6. c 7. c 8. a 9. b 10. a 11. b 12. a 13. b 14. a 15. d 16. a 17. d 18. d 19. d 20. b 21. c 22. a 23. a 24. b 25. b Fill in the Blank 1. 4.722 kcal/mol 2. 9.572 kcal/mol 3. 2400-3300 cm-1 4. 1630-1800 cm-1 5. alcohol 6. carbonyl 7. 5 8. 3 9. 2800-3000 cm-1 10. 1600-1680 cm-1 True-False 1. F 2. T 3. F 4. T 5. F 6. T 7. T 8. T 9. T 10. F
Chapter 12 Nuclear Magnetic Resonance Spectroscopy
138
Multiple Choice 1. How many sets of equivalent hydrogen atoms are there for 2-propanol? (Sec. 12.6)
a) 2 b) 3 c) 4 d) 8
2. How many sets of equivalent hydrogen atoms are there for the following compound? (Sec. 12.6)
a) 3 b) 4 c) 5 d) 6
3. How many sets of signals are there in the 1H-NMR spectrum for 1,1-dichlorocyclohexane? (Sec. 12.6)
a) 2 b) 3 c) 4 d) 6
4. How many sets of signals are there in the 1H-NMR spectrum for diisopropyl ether? (Sec. 12.6)
a) 1 b) 2 c) 3 d) 6
5. How many sets of equivalent carbon atoms are there for the following compound? (Sec. 12.10)
a) 3 b) 4 c) 5 d) 6
6. How many sets of equivalent carbon atoms are there for 1-bromo-3-chlorocyclohexane? (Sec. 12.10)
a) 3 b) 4 c) 5 d) 6
CH3
CH3
OH
Chapter 12 Nuclear Magnetic Resonance Spectroscopy
139
7. A compound gave two sets of signals in the 1H-NMR spectrum with an integration ratio of 60 to 10. Which is the most likely structure for the compound? (Sec. 12.6, 12.7)
8. Which are the relative areas of integration in the 1H-NMR spectrum for 2-chloro-3-methylbutane? (Sec. 12.7)
a) 9:1:1 b) 3:3:3:1:1 c) 6:3:2 d) 6:3:1:1
9. Which is the order of increasing G values downfield from TMS for the methyl groups shown (lowest first)? (Sec. 12.8)
a) I, III, IV, II b) II, I, III, IV c) IV, II, III, I d) III, IV, II, I
10. Which is the order in increasing chemical shift values in the 1H-NMR spectrum for the indicated hydrogen atoms (lowest first)? (Sec. 12.8)
a) IV, II, III, I b) I, III, II, IV c) III, I, IV, II d) II, IV, I, III
CH3CH2CH2CCH2CH2CH3
O
H3C OH
O
CH3
CH3
CHCCH
O CH3
CH3
H3C
H3C
a) b)
c) d)
CH3 CH CH CH2 COH
O
I II III IV
CH3 Br CH3 I CH3 OH CH3 F
I II III IV
Chapter 12 Nuclear Magnetic Resonance Spectroscopy
140
11. Which is the splitting pattern for the indicated hydrogen atom? (Sec. 12.9)
a) septet b) quartet c) doublet d) singlet
12. Which is the splitting pattern for the hydrogen atoms in 2,2-dibromopropane? (Sec. 12.9)
a) septet b) quartet c) doublet d) singlet
13. The splitting pattern for a compound with molecular formula C3H5OCl gave a quartet and a triplet. Which is the most likely structure for this compound? (Sec. 12.9)
14. Which compounds show signal splitting in the 1H-NMR spectrum? (Sec. 12.9)
a) I, II b) III, IV c) I, III d) II, IV
15. Which compound has a singlet in the 1H-NMR at approximately 2.0 ppm and integrates to 3 hydrogens? (Sec. 12.8, 12.9)
CH3CCH2Cl
O
CH3CH2CCl
O
ClCH2CH2CH
OO Cla) b)
c) d)
CH3COC
O CH3
CH3
CH3 C COCH2CH3
OCH3
CH3
CH3 C
CH3
CH3
CH3
CH3O OCH3
I II III IV
CH3CHOCH
O
CH3
CH3COCH2CH3
O
CH3CH2CH2OCH
O
CH3OCCH2CH3
O
a) b)
c) d)
CH3COCH
O CH3
CH3
Chapter 12 Nuclear Magnetic Resonance Spectroscopy
141
16. Which compound has four sets of signals in the 1H-NMR spectrum? (Sec. 12.6)
17. Which compounds have 3 signals in the 13C NMR spectrum? (Sec. 12.10)
OH OH OH OH
OH
OH
OHI II III IV
a) I, II b) I, II, III c) I, III d) I, II, III, IV
18. Which is the order of increasing G values in the 13C NMR spectra for the following carbon atoms? (Sec. 12.8)
CH4 CH3F CH3Br CH3OH CH3Cl I II III IV V
a) III, V, II, IV, I b) I, IV, II, V, III c) V, IV, II, III, I d) I, III, V, IV, II
19. A compound has a single signal in the 13C NMR spectrum and a single signal in the 1H-NMR spectrum. Which is most likely the compound? (Sec. 12.6, 12.10)
a) dimethyl ether b) diethyl ether c) 2,2-dimethylpropane d) methyl ethanoate
20. A compound has two signals in the 13C NMR spectrum and a single signal in the 1H-NMR spectrum. Which is most likely the compound? (Sec. 12.6, 12.10)
a) dimethyl ether b) diethyl ether c) 2,2-dimethylpropane d) methyl ethanoate
CH3CHOCH
O
CH3
CH3COCH2CH3
O
CH3CH2CH2OCH
O
CH3OCCH2CH3
O
a) b)
c) d)
Chapter 12 Nuclear Magnetic Resonance Spectroscopy
142
21. A compound has three signals in the 13C NMR spectrum and two signals in the 1H-NMR spectrum. Which is most likely the compound? (Sec. 12.6, 12.10) a) bromobenzene b) para dibromobenzene c) ortho dibromobenzene d) meta dibromobenzene 22. Which are the characteristic shift ranges for the indicated hydrogen atoms? (Sec. 12.8)
a) I = 0.8-1.0, II = 6.5-8.5, III = 2.2-2.5, IV = 2.1-2.3 b) I = 0.8-1.0, II = 2.2-2.5, III = 6.5-8.5, IV = 2.1-2.3 c) I = 2.2-2.5, II = 6.5-8.5, III = 0.8-1.0, IV = 2.1-2.3 d) I = 2.2-2.5, II = 6.5-8.5, III = 2.1-2.3, IV = 0.8-1.0
23. The compounds shown below can be distinguished by which 1H-NMR characteristics? (Sec. 12.11)
O
O
I) number of signals II) splitting III) integration IV) chemical shift a) I, II, IV b) I, IV c) II d) IV
H3C CCH2CH2CH3
O
HI
II
III IV
Chapter 12 Nuclear Magnetic Resonance Spectroscopy
143
24. The compounds shown below can be distinguished by which 1H-NMR characteristics? (Sec. 12.11)
Cl
Cl
ClCl
I) number of signals II) splitting III) integration IV) chemical shift a) I, II b) I, IV c) I, II d) IV 25. The compounds shown below can be distinguished by which 1H-NMR characteristics? (Sec. 12.11)
O
O O
I) number of signals II) splitting III) integration IV) chemical shift a) I, II, III b) I, III, IV c) I, II d) IV Fill in the Blank 1. The number of 1H signals for the following molecule is _____________. (Sec. 12.6)
O
O
Chapter 12 Nuclear Magnetic Resonance Spectroscopy
144
2. The number of 1H signals for the following molecule is _____________. (Sec. 12.6)
CH3
CH3 3. The number of 1H signals for isopropyl ethyl ether is _____________. (Sec. 12.6) 4. The splitting of the three 1H signals of methyl propanoate are (left to right as drawn) _____, ______, ______. (Sec. 12.9)
O
O 5. The splitting of the three 1H signals of tetrahydropyran are (top to bottom as drawn) _____, ______, ______. (Sec. 12.9)
O
6. The integration of the 1H signal at 2.2 ppm for 3-pentanone is _________. (Sec. 12.7)
O 7. The integration of the 1H signal at 3.8 ppm for dipropyl ether is _________. (Sec. 12.7, 12.8) 8. The number of 13C signals for meta dimethoxybenzene is ________. (Sec. 12.10) 9. The expected chemical shift range (in ppm) for the indicated carbon of ethyl benzoate is ___________. (Sec. 12.10)
O
O
Chapter 12 Nuclear Magnetic Resonance Spectroscopy
145
10. The expected chemical shift range (in ppm) for the indicated protons of E-2-pentene is ___________. (Sec. 12.8)
H
H
True-False 1. The number of 1H-NMR signals for propyl propanoate is 3. (Sec. 12.6)
O
O
2. The number of 1H-NMR signals for para methoxytoluene is 4. (Sec. 12.6) 3. The splitting of the signal for the indicated protons of 3-methylcyclohexanone is a quartet. (Sec. 12.9)
O
CH3
H
4. The splitting of the signal for the indicated protons of isopropyl formate is a septet. (Sec. 12.9)
O
O CH3
CH3H H
5. The integration of the signal that includes the indicated protons of isopropyl formate is 3. (Sec. 12.7)
O
O CH3
CH3H H
Chapter 12 Nuclear Magnetic Resonance Spectroscopy
146
6. The integration of the signal that includes the indicated protons of meta hydroxybenzene is 2. (Sec. 12.7) OH
OHH
7. Ethyl 3-oxopentanoate has 5 proton signals and 5 carbon signals in the NMR spectra. (Sec. 12.6, 12.10)
O
O O
8. 1,4-Cyclohexanedione has 2 proton signals and 4 carbon signals in the NMR spectra. (Sec. 12.6, 12.10)
O
O 9. A 1H-NMR shows a single signal and a 13C-NMR shows two signals. A possible structure for this compound is,
O
(Sec. 12.6, 12.10) 10. A 1H-NMR shows a single signal and a 13C-NMR shows two signals. A possible structure for this compound is,
O (Sec. 12.6, 12.10)
Chapter 12 Nuclear Magnetic Resonance Spectroscopy
147
Answers Multiple Choice 1. b 2. d 3. b 4. b 5. c 6. d 7. d 8. d 9. b 10. b 11. a 12. d 13. c 14. d 15. b 16. c 17. d 18. d 19. a 20. c 21. c 22. d 23. d 24. b 25. b Fill in the Blank 1. 4 2. 4 3. 4 4. t, q, s 5. t, q(5), q(5) 6. 4 7. 4 8. 5 9. 165-200 ppm 10. 5-5.7 ppm True-False 1. F 2. T 3. F 4. T 5. F 6. T 7. F 8. F 9. T 10. T
Chapter 13 Aldehydes and Ketones
148
Multiple Choice 1. Which compounds are named correctly? (Sec. 13.3)
a) I, II, III b) IV, V, VI c) II, IV, V d) III, IV, VI
2. Which is the correct structure for 2-hydroxybenzophenone? (Sec. 13.3)
3. How many chiral ketones are there that have the molecular formula C6H12O? (Sec. 13.2)
a) 1 b) 2 c) 3 d) 4
cinnamaldehydeVI
benzophenoneV
1,3-butanedioneIV
2-hydroxypropanoic acidIII
2-methylbenzaldehydeII
o-hydroxybenzaldehydeI
C C
H H
C O
CH3
CH3CCH2CH
O O
CH3CHCOH
HO O
CCH3
O
CH3
CH
OOH
CH
O
d)c)
b)a)
OH
CH
O
C CH3
OH
O
C
O
OH
CH3CH
OH
CH
O
Chapter 13 Aldehydes and Ketones
149
4. Which compounds are acetals? (Sec. 13.7)
a) I, II, III b) IV, V, VI c) III, IV, VI d) II, IV, V
5. Which is the product of the following reaction? (Sec. 13.7)
6. Which compound reacts with aqueous acid to give an aldehyde? (Sec. 13.7)
O CH3 O OH
O
O
CH3
CH3O
O
O
O CH3
CH3
O OCH3
I II III
IV V VI
O O H3OH2O
O
OH3C
O
HOCH3
O
OCH3
OCH3
CH3a) b) c) d)
d)c)
b)a)
+
++
CH3OHHCCH2CH
O O
CH3CCH2CH2CH2CH
O O
HCH
O
HOCH2CH2CH2OHCH3OHCH3CH2CH
O
Chapter 13 Aldehydes and Ketones
150
7. A Grignard reagent is prepared by reacting cyclopentanol with first thionyl chloride and then magnesium in ether. The Grignard reagent is then reacted with acetaldehyde (ethanal) and the reaction mixture acidified. What is the major final product of this series of reactions? (Sec. 13.6)
8. Which is the major product of the reaction of ethyl Grignard and propiophenone (ethyl phenyl ketone)? (Sec. 13.6)
9. Which is the major product of the following reaction? (Sec. 13.11)
10. Which reaction does not lead to 3-methyl-3-hexanol? (Sec. 13.6)
a) 2-butanone + propylmagnesium bromide b) 3-hexanone + methyl magnesium bromide c) 2-pentanone + ethylmagnesium bromide d) 3-pentanone + ethylmagnesium bromide
a) b) c) d)CHCH3
OH OH
CH2CH3
CH2CH2OH CH2OCH3
CCH2CH3
CH2CH3
OH
CCH3
CH2CH3
OH
CCH2CH3
CH3
OH
CCH3
CH3
OH
a) b)
c) d)
ONaBH4
H2OHCl Mg
ether
O
OH OH
OH HO
a) b)
c) d)
Chapter 13 Aldehydes and Ketones
151
11. Which is the major product of the following reaction? (Sec. 13.6)
12. Which is the major product of the following reaction? (Sec. 13.6)
13. Which is the major product of the reaction of cyclopentylamine and benzaldehyde followed by nickel and hydrogen? (Sec. 13.8)
D H ND2 NDCH2CH3a) b) c) d)
CCH3
O
CH3MgBr+ ether H3O
CCH3
CH3
OH
CH2CHCH3
OH
CHCH2OH
CH3
CHCH2CH3
OH
a) b)
c) d)
CH2NH NH
NHCH2 CH2NHCH2
a) b)
c) d)
ether+ CH3CH2ND2MgBr
Chapter 13 Aldehydes and Ketones
152
14. The following product can be made from the reductive amination of which combination of compounds? (Sec. 13.8)
a) benzaldehyde and benzylamine b) benzaldehyde and aniline c) benzophenone and ammonia d) acetophenone and ammonia
15. Which is the major product of the following reaction? (Sec. 13.11)
16. 1-Hexene was treated with dilute sulfuric acid. The product of that reaction was reacted with potassium dichromate in sulfuric acid. This product was then treated with methanol in hydrochloric acid. What is the major product of this series of reactions? (Sec. 13.7, 13.10)
CH
NH2
CH
ONaBH4
H2O
COH
O
CH2OH
CH
O
CH2OH
a) b)
c) d)
d)c)
b)a)
CH3CH2CH2CH2CH2CCH3
O
CH3CH2CH2CH2CH2COCH3
O
CH3CH2CH2CH2CCH3
OCH3
OCH3
CH3CH2CH2CH2CH2CH
OCH3
OCH3
Chapter 13 Aldehydes and Ketones
153
17. Which oxidation conditions are used in the industrial transformation of cyclohexanone to adipic acid? (Sec. 13.10)
18. Which is the best procedure for the following preparation? (Sec. 13.6, 13.10, 13.11)
19. Which is the best procedure for the following preparation? (Sec. 13.8)
a) K2Cr2O7 / H2SO4
b) KMnO4
c) HNO3
d) AgNO3 / NH3
CH
O
CH2CH
O
CH3MgBrH2SO4
K2Cr2O7
H2SO4
Ag(NH3)2
NH3/H2ONaBH4
H2O
HCl Mgether
H2CO PCC
LiAlH4
H2OHBr CO2
H3O+
CH3MgBrH2SO4
NaBH4
H2O
Mgether
a)
b)
c)
d)
O N
NaBH4
H2O
Ni / H2
HN HNNaBH4
H2O
HN
Ni / H2
HN
a) b)
c) d)
Chapter 13 Aldehydes and Ketones
154
20. Which compound is a Schiff base? (Sec. 13.8)
21. Arrange the compounds in order of increasing solubility in water (least first). (Sec. 13.4)
a) I, II, III, IV b) IV, I, II, III c) IV, III, II, I d) II, II, I, IV
22. Arrange the compounds in order of increasing solubility in water (least first). (Sec. 13.4)
a) II, I, IV, III b) I, II, IV, III c) III, IV, I, II d) II, I, IV, III
23. Arrange the compounds in order of increasing boiling point (lowest first). (Sec. 13.4)
a) II, I, IV, III b) I, II, IV, III c) III, IV, I, II d) II, I, IV, III
IVIIIIII
CHCH2CH2CH2CH2CCH3
H3C
H3C
OCH
O
O CH3CH2CH
O
IVIIIIII
CH3CH2
OCH2CH3CH3CH2CH2CH2CH3CH3CH2CH2CH2
OH
CH3CH2CH2CH
O
NH2 NHNH2N CH3CH2NH3 CH3a) b) c) d)
IVIIIIII
CH3CH2
OCH2CH3CH3CH2CH2CH2CH3CH3CH2CH2CH2
OH
CH3CH2CH2CH
O
Chapter 13 Aldehydes and Ketones
155
24. Arrange the compounds in order of increasing boiling point (lowest first). (Sec. 13.4)
a) III, II, I, IV b) IV, I, II, III c) IV, III, II, I d) II, II, I, IV
25. Which structure is the major tautomer of 2-pentanone in aqueous acid? (Sec. 13.9)
Fill in the Blank 1. The IUPAC name of the following structure is ___________________________. (Sec. 13.3)
OO
Br 2. The IUPAC name of the following structure is ___________________________. (Sec. 13.3)
O O
3. The major product that completes the following reaction is,
O
H
MgBr1)
2) H+, H2O
, ether
(Sec. 13.6)
OH OH OH OH
a) b) c) d)
IVIIIIII
CHCH2CH2CH2CH2CCH3
H3C
H3C
OCH
O
O CH3CH2CH
O
Chapter 13 Aldehydes and Ketones
156
4. The starting material that completes the following reaction is,
MgBr OH1) , ether
2) H+, H2O
(Sec. 13.6) 5. The starting material that completes the following reaction is,
O
OOH OH
H+
(Sec. 13.7) 6. The reagents that complete the following reaction are,
O N
(Sec. 13.8) 7. The starting material that completes the following reaction is,
NH2
NH3
H2, Ni (Sec. 13.8)
8. The reagents that complete the following reaction are,
H
O
OH
O
(Sec. 13.10)
Chapter 13 Aldehydes and Ketones
157
9. The major product that completes the following reaction is,
O
1) LiAlH4, ether
2) H2O
(Sec. 13.11) 10. The reagents that complete the following reaction are,
H
O OH
(Sec. 13.11) True-False 1. The name of the following molecule is 1,5-cyclohexanecarbaldehyde. (Sec. 13.3)
H
O
2. The name of the following compound is 3-cyclohexenone. (Sec. 13.3)
O
3. The order of boiling points for the following functional groups, of similar molecular weights, is, ether > aldehyde > alcohol > carboxylic acid (Sec. 13.4) 4. The enol form of cyclohexanone is,
OH
(Sec. 13.9)
Chapter 13 Aldehydes and Ketones
158
5. The product of the reaction of acetone (propanone) with bromine and acetic acid is 1-bromo-2-propanone. (Sec. 13.9) 6. The product of the reaction of 2-hydroxybutanal with phenyl magnesium bromide is 1-phenyl-1,2-butanediol. (Sec. 13.6) 7. The product of the reaction of benzaldehyde with silver ammonium nitrate (Tollen’s reagent) is benzoic acid. (Sec. 13.10) 8. The product of the reaction of 3-pentanone with ammonia, hydrogen, and nickel is 3-pentanamine. (Sec. 13.8) 9. The mechanism for the formation of the enol form of propanal under basic conditions (NaOH) is,
O
H
H
O
H
H-OH
Na+
+ H2O
(Sec. 13.9) 10. Two ways to drive the acetal reaction to completion are to use excess alcohol and remove water produced. (Sec. 13.7)
Chapter 13 Aldehydes and Ketones
159
Answers Multiple Choice 1. a 2. b 3. b 4. c 5. b 6. c 7. a 8. a 9. a 10. d 11. a 12. a 13. c 14. c 15. b 16. b 17. c 18. c 19. c 20. d 21. b 22. c 23. c 24. a 25. c Fill in the Blank 1. R – 4-bromo-5-oxohexanal 2. E – 4-nonene-2,8-dione 3.
OH
H
4.
O
Chapter 13 Aldehydes and Ketones
160
5.
H
O
6.
NH2
Ni, H2 7.
H
O
8. H2CrO4 or Ag+ conditions 9.
OH 10. 1) NaBH4, ethanol 2) H2O True-False 1. F 2. T 3. F 4. F 5. T 6. F 7. T 8. T 9. F 10. T
Chapter 14 Carboxylic Acids
161
Multiple Choice
1. Which is the IUPAC name for the following compound? (Sec. 14.3)
a) 2-oxohexanoic acid
b) 5-oxohexanoic acid
c) methyl butyroxo ketone
d) 4-ketopentanoic acid
2. Which is the correct structure for Z-3-hexenedioic acid? (Sec. 14.3)
3. Which is the IUPAC name for the following compound? (Sec. 14.3)
a) E-3-phenylpropenoic acid
b) Z-3-carboxy-1-phenylethene
c) E-1-phenylpropenoic acid
d) Z-benzylacrylic acid
H3CC
O
CH2 CH2 CH2 C
O
OH
CH2COH
O
C
CH2COH
O
H H
C
CH
CH2COH
O
HOCH2C
O
H
C
C
H
H
CH2COH
O
CH2COH
O
H
COH
O
COH
O
H
a)b)
c) d)
C C
COHH
O
H
Chapter 14 Carboxylic Acids
162
4. Which is the structure for potassium hydrogen oxalate? (Sec. 14.3)
5. Which structures are correctly named (common name)? (Sec. 14.3)
a) I, II
b) II, III
c) III, IV
d) II, IV
CH2
CO K
O
COH
O
CH2 4
CO K
O
COH
O
CO K
COH
O
O
CO K
O
COH
O
a) b) c) d)
CH3COH
O
H2C CHCOH
O
COH
CH2
COH
O
O
COH
COH
O
O
formic acid acrylic acid
malonic acid succinic acid
I II
III IV
Chapter 14 Carboxylic Acids
163
6. Arrange the compounds in order of increasing solubility in water (least soluble first). (Sec. 14.4)
a) II, III, I, IV
b) IV, I, III, II
c) I, IV, II, III
d) II, III, I, IV
7. Arrange the compounds in order of increasing order of solubility in water (least soluble first).
(Sec. 14.4)
a) IV, III, I, II
b) I, III, II, IV
c) IV, II, III, I
d) I, II, III, IV
8. Which compounds are soluble in water? (Sec. 14.4)
a) I, II, IV
b) I, III, IV
c) I, II, III
d) II, III, IV
HOC
O
CH2 CH2 CH3 K OC
O
CH2 CH2 CH3
HOC
O
CH3 HOC
O
I II
IIIIV
COH
O
CO K
O
CO K
O
CO K
O
COH
O
COH
O
C
CO
O
O
I II III IV
IVIIIIII
CH3CH2CH3H3C
C
O
CH3HOCH2CH2CH3HOC
O
CH2 CH3
Chapter 14 Carboxylic Acids
164
9. Arrange the compounds in order of increasing boiling point (lowest first). (Sec. 14.4)
a) II, I, III, IV
b) I, II, III, IV
c) III, I, II, IV
d) IV, I, II, III
10. Arrange the compounds in order of increasing boiling point (lowest first). (Sec. 14.4)
a) I, II, III, IV
b) IV, II, II, I
c) II, III, I, IV
d) I, II, IV, III
11. Arrange the compounds in order of increasing acidity (lowest first). (Sec. 14.5)
a) IV, I, II, III
b) III, II, IV, I
c) IV, II, I, III
d) II, I, III, IV
C
CH3
H
OH COH
O
CO Na
OC
O
CH3
I II III IV
HOCCH2CH2COH
O O
HOCCH2CH2CH3
O
HOCCH2CH2CH2CH2CH3
O
HOCCH2CH2CH2CH2COH
O O
I II III IV
IVIIIIII
CH3CH2COH
O
C
Cl
Cl
CH3 COH
O
C
Cl
CH3
H
COH
O
CH2CH2COH
O
Cl
Chapter 14 Carboxylic Acids
165
12. Arrange the compounds in order of increasing acidity (lowest first). (Sec. 14.5)
C
O
OH Cl CH2
COH
O
CH3CH
2COH
O
CH3
CH
COH
OOH
I II III IV
a) III, II, I, IV
b) I, II, IV, III
c) II, III, I, IV
d) II, I, III, IV
13. Arrange the compounds in order of increasing acidity (lowest first). (Sec. 14.5)
a) IV, I, III, II
b) III, II, I, IV
c) II, III, I, IV
d) III, II, IV, I
COH
O
Cl
COH
O
COH
O
CH3
COH
O
NO2
I II III IV
Chapter 14 Carboxylic Acids
166
14. Which reactions proceed nearly to completion as written? (Sec. 14.5)
a) I, II
b) III, IV
c) I, III
d) II, IV
15. Which mixtures can be separated by treatment with aqueous NaOH? (Sec. 14.5)
a) I, II
b) III, IV
c) II, IV
d) I, III
OH CH2OH COH
O
CH2COH
O
COH
O
CH2OH COH
O
OH
and and
and and
III
III IV
+
+
+
+
+
+
+
+
IV.
III.
II.
I.
COH
O
CH3CO Na
O
CO Na
O
CH3COH
O
H2SO4CH3CO Na
O
NaHSO4CH3COH
O
H2CO3CH3CO Na
O
Na2CO3CH3COH
O
H2OCH3CO Na
O
NaOHCH3COH
O
Chapter 14 Carboxylic Acids
167
16. Which reactions yield the same carboxylic acid? (Sec. 13.10)
a) I, II
b) III, IV
c) II, IV
d) I, III
17. Which compounds undergo thermal decarboxylation? (Sec. 14.9)
a) I, II
b) II, III
c) III, IV
d) II, IV
CH2CH
O
CH2CH2Br
CH2CH3
CH2OH
K2Cr2O7
H2SO4
+ Mgether CO2 H3O
KMnO4
OH
H3O
H2SO4
K2Cr2O7
I.
II.
III.
IV.
COH
O
COH
O
COH
O
COH
O
C
O
C
COH
O
CH3
CH3
O
CH2COH
O
I. II.
III. IV.
Chapter 14 Carboxylic Acids
168
18. Which conditions are best for the transformation? (Sec. 14.6)
a) LiAlH4
b) NaBH4
c) Ag(NH3)2OH / NH4OH
d) Pyridine . Cr3O4
19. Which conditions are best for making the following compound? (Sec. 14.7)
20. The following compound is prepared by Fischer esterification of which combination of reagents?
(Sec. 14.7)
a) 1,2-dihydroxybenzene and methanol
b) salicylic acid and methanol
c) phthalic acid and methanol
d) benzoic acid and methanol
O COH
O
HO COH
O
COCH3
O
COCH3
O
CH3
C
O
OCH2CH2CH3
d)
c)
b)
a)
+
++
+ +
++
CH3CH2CH2O Na
HClCH3CH2CH2OH
HCl
HClCH3OH CH3CH2COH
O
CH3COH
O
CH3CH2COH
O
CH3COH
O
CH3COH
O
Chapter 14 Carboxylic Acids
169
21. Which compound is prepared by reaction of benzoic acid with ammonia and water? (Sec. 14.5)
22. Which conditions will convert pentanoic acid to pentanoyl chloride? (Sec. 14.8)
a) HCl
b) NaCl
c) SOCl2
d) LiAlH4 followed by HCl
23. Acetophenone (methyl phenyl ketone) is the product from thermal degradation of which compound?
(Sec. 14.7)
24. A mixture of the following compounds was extracted in the order 1) 1 M HCl, 2) 1 M NaOH, 3) ether.
Which compound is extracted into the basic layer? (Sec. 14.5)
a) I
b) II
c) III
d) All of the above
C
O
NH2
C
O
O NH4
CO
O
NH3
CH2NH2
a) b) c) d)
CH2 C
COH
O
H
COH
O
CCH2COH
O O
C
COH
O
H
CCH3
O
CH2CCH2COH
O O
a) b) c) d)
NH2 COH
O
C
O
CH3
I II III
Chapter 14 Carboxylic Acids
170
25. A mixture of the following compounds was extracted in the order 1) 1 M HCl, 2) 1 M NaOH, 3) ether.
Which compound is extracted into the ether layer? (Sec. 14.5)
a) I
b) II
c) III
d) All of the above
Fill in the Blank
The IUPAC name of the following structure is ___________________________. (Sec. 14.3)
OH
O
2. The IUPAC name of the following structure is ___________________________. (Sec. 14.3)
OH
O O
3. The major product that completes the following reaction is,
O
OH
1) LiAlH4, ether
2)H2O
(Sec. 14.6)
NH2 COH
O
C
O
CH3
I II III
Chapter 14 Carboxylic Acids
171
4. The reagents that complete the following reaction are,
OH
O O
OH
OH O
(Sec. 14.6)
5. The major product that completes the following reaction is,
O
OHOH
H+
(Sec. 14.7)
6. The reagents that complete the following reaction are,
OH
O
Cl
O
(Sec. 14.8)
7. The major product that completes the following reaction is,
OH
O Oheat
(Sec. 14.9)
8. The reagents that complete the following reaction are,
OH
O
O
O
(Sec. 14.7)
Chapter 14 Carboxylic Acids
172
9. The reagents that complete the following reaction are,
OH
O O
OH
(Sec. 14.6)
10. Complete the following reaction mechanism for the Fisher esterification of acetic acid. (Sec. 14.7)
OH
O
OH
OH
OH
OH
OCH3H
OH2
OH
OCH3
OH
OCH3OCH3
O
H+ +
HOCH3
H+
++
+
True-False
1. The order of acidity of the following carboxylic acids is,
OH
O
ClOH
OCl
OH
OCl
OH
O
> >>
(Sec. 14.5)
2. The order of acidity of the following carboxylic acids is,
OH
O
ClOH
O
Cl
ClOH
O
Cl
Cl
Cl
OH
O
> > >
(Sec. 14.5)
Chapter 14 Carboxylic Acids
173
3. The order of acidity of the following carboxylic acids is,
OH
O
ClOH
O
F OH
O
BrOH
O
> > >
(Sec. 14.5)
4. The name of the following compound is 2,2-dibromopropanedioic acid. (Sec. 14.3)
OH OH
O O
Br Br
5. The order of boiling points for the following compounds is,
OH
O
OOHO> > >
(Sec. 14.4)
6. The structure of Z-2-butendioic acid is,
OHOH
O
O (Sec. 14.3)
7. The product of heating 4-oxopentanoic acid is butanone and carbon dioxide. (Sec. 14.9)
8. The product of the reaction of hexanoic acid and chromic acid is hexanol. (Sec. 13.10)
9. The product of the reaction of benzoic acid and sodium hydroxide is sodium benzoate. (Sec. 14.5)
10. The product of the reaction of acetic acid and thionyl chloride is acetyl chloride. (Sec. 14.8)
Chapter 14 Carboxylic Acids
174
Answers
Multiple Choice
1. b
2. c
3. a
4. c
5. b
6. b
7. a
8. c
9. d
10. c
11. c
12. c
13. b
14. a
15. d
16. b
17. b
18. b
19. c
20. c
21. b
22. c
23. b
24. b
25. c
Fill in the Blank
1. 2,4-cyclopentadiene carboxylic acid
2. 2,2-dimethyl-3-oxobutanoic acid
3.
OH
4. 1) NaBH4, ethanol, 2) H2O
5.
O
O
6. SOCl2
7.
CH3
O
8. phenol, H
+
Chapter 14 Carboxylic Acids
175
9. Pt, H2
10.
OH
O
OH
OH
OH
OH
OCH3H
OH2
OH
OCH3
OH
OCH3OCH3
O
H+ +
HOCH3
H+
++
+
True-False
1. F
2. T
3. F
4. T
5. F
6. F
7. F
8. F
9. F
10. T
Chapter 15 Functional Derivatives of Carboxylic Acids
176
Multiple Choice 1. Which is the correct structure for phenyl benzoate? (Sec. 15.2)
2. Which compounds are named correctly? (Sec. 15.2)
a) I, II, III b) II, III, IV c) I, IV, V d) III, IV, V
3. Which is the common name for the following compound? (Sec. 15.2)
a) aspirin b) cyclosporin c) succinamide d) salicylamide
CO
O
CH2OC
O
OCCH2
O
CH2OCCH2
O
a) b)
c) d)
OH
CNH2
O
N,N-dimethylformamideV
J-butyrolactoneIV
ethyl acetateIII
cyclohexyl anhydrideII
succinic anhydrideI
HCN
OCH3
CH3
CH3CH2COCH3
OO O
OO
OO O
Chapter 15 Functional Derivatives of Carboxylic Acids
177
4. Which functional groups are correctly named? (Sec. 15.2)
a) II, III, IV b) III, IV, V c) II, III, V d) I, II, IV
5. What is the order of decreasing reactivity toward nucleophilic acyl substitution for these carboxylic acid derivatives (most reactive first)? (Sec. 15.3)
a) II, IV, I, III b) III, IV, I, II c) IV, I, II, III d) I, II, III, IV
6. Carboxylic acids and amides have in general higher boiling points than esters and anhydrides because of which property? (Sec. 15.2, 14.4)
a) dispersion forces b) resonance stabilization c) conjugated functional groups d) hydrogen bonding
O O
CH3CH2COCH3
OHCN
OCH3
CH3
CH3CH2COCCH2CH3
O O
CH3CCl
O
lactoneIV
anhydrideI
amideII
esterIII
acyl chlorideV
CH3COCH3
O
CH3CCl
O
CH3CNH2
O
CH3COCCH3
O O
I II III IV
Chapter 15 Functional Derivatives of Carboxylic Acids
178
7. Which is the order of increasing boiling point of the following compounds (lowest first)? (Sec. 15.2, 14.4)
a) IV, I, III, II b) I, III, IV, II c) II, I, III, IV d) IV, III, II, I
8. Which is the order of increasing solubility in water of the following compounds (least first)? (Sec. 15.2, 14.4)
a) I, III, II, IV b) III, I, IV, II c) I, IV, II, III d) II, I, III, IV
9. Which reactions proceed at room temperature as written? (Sec. 15.4, 15.6, 15.7)
a) I, II b) I, III c) II, III d) II, IV
CH3CH2CCl
O
CH3CH2CNH2
O
CH3COCCH3
O O
HCOCH2CH3
O
H2O
H2O
NH3
NH3
+
+
+2
+
CH3CH2COH
O
CH3CH2COH
O
CH3CNH2
O
CH3CO
O
HCNH2
O
CH3CH2OH
HCl
NH3
NH4
+
+
+
+
I
II
III
IV
CH3COH
O
IVIIIIII
CH3CNH2
O
CH3CCl
O
CH3COCH3
O
CH3CH2COH
O
CH3CH2CNH2
O
CH3CH2CCl
O
IVIII
III
CH3CH2COCH3
O
Chapter 15 Functional Derivatives of Carboxylic Acids
179
10. The following reaction is fastest when Z is which group? (Sec. 15.3)
11. Which is the major product when 1,2-diaminoethane is heated with dimethyl oxalate? (Sec. 15.6)
12. Which are the best conditions for the following preparation? (Sec. 15.6)
C
O
Z + OH CO
O
HZ+
O CH3 CH3O CH3CO
O
a) b) c) d)
CH3CN
O
H
CH2CH2 NCCH3
H
O
O O
O O
HN NH
O O
CH3CN C NCCH3
O O
CH3
H
H H
a) b)
c) d)
COH
O
CH3CH3
CN
O CH3
CH3
SOCl2 (CH3)2NH
NaOH
NH3 CH3CH2Br
room temp
(CH3)2NH
(CH3)2NH
a)
b)
c)
d)
Chapter 15 Functional Derivatives of Carboxylic Acids
180
13. Which compounds will yield benzoic acid when hydrolyzed? (Sec. 15.4)
I) benzyl ethanoate II) benzamide III) phenyl ethanoate IV) methyl benzoate
a) I, II b) III, IV c) I, III d) II, IV
14. Which is the product from the following reaction? (Sec. 15.6, 15.9)
O
ONH3 1) LiAlH4
2) H2O
15. Which of the following compounds does not yield nicotinamide when reacted with ammonia at room temperature? (Sec. 15.6)
N
Cl
O
N
OH
O
N
O
O O
CH3
N
O
OCH3
I II III IV
a) I, II b) II, IV c) II, III d) III, IV
N
H
N
H
OH
NH2
CH2CH2OH
a) b) c) d)
OH
CH2CH2NH2
Chapter 15 Functional Derivatives of Carboxylic Acids
181
16. Which is the product of the reaction of 4-aminophenol with 1 equivalent of acetic anhydride? (Sec. 15.5)
17. Which is the product of the reaction of phthalic anhydride with 1 equivalent of methanol? (Sec. 15.5)
18. Which reactions can be used to prepare an ester? (Sec. 15.5)
a) II, IV b) I, III c) I, II d) III, IV
NH2
OCCH3
O
OH
HNCCH3
O
CCH3
ONH2
OH OCCH3
O
HNCCH3
O
a) b) c) d)
COH
COCH3
O
O
COCH3
COCH3
O
O
CCH3
COH
O
O
COCCH3
COH
O
O
O
a) b) c) d)
COH
O
CO Na
O
COH
O
CNH2
O
SOCl2
H3O
OH
+OH
+OH
OH+
heat
I
II
III
IV
Chapter 15 Functional Derivatives of Carboxylic Acids
182
19. Which is the final product of a series of reactions starting with ethyl benzoate and reacting with 1) aqueous sulfuric acid and heat, 2) thionyl chloride, and 3) ethylamine? (Sec. 15.4, 15.6)
20. Which is the product from the reaction of sodium benzoate and acetyl chloride? (Sec. 15.5, 15.6)
NCH2CH3
H
CNCH2CH3
O
H
NCCH3
O
H
CHNCH2CH3
OH
H
a) b)
c) d)
COCH3
O
OCCH3
O
CCH3
O
COCCH3
O O
a) b)
c) d)
Chapter 15 Functional Derivatives of Carboxylic Acids
183
21. Partial hydrolysis of phenobarbitol gives which compound? (Sec. 15.4)
a) I, II b) II, III c) III, IV d) I, III
22. Which is the product of the reaction of ethyl benzoate with 2 equivalents of methyl grignard followed by aqueous acid? (Sec. 15.8)
NH
NH
O
O
O
C6H5
CH3CH2
H2NCNH2
O
C
COH
O
COH
O
CH2CH3
H2NCCOH
OO
CNH2
COH
O
CH2CH3
I II
III IV
COH
CH3
CH3
CCH3
O
COCH3
O
CH2CH2CH3
a) b) c) d)
Chapter 15 Functional Derivatives of Carboxylic Acids
184
23. Which is the major product of the following reaction? (Sec. 15.8)
24. Which are the best conditions for the following reaction? (Sec. 15.9)
O
O
1) CH3CH2MgBr
2) H3O+
OHHO
CH3CH2 CH2CH3
OHO
CH2CH3
HO
CH3CH2 CH2CH3
OHCH3
CH3CH2 CH2CH3
a) b)
c) d)
CH3CH2CH2COCH2CH3
O
CH3CH2CH2CH2OH
1) NaBH4 / ether
2) H2O
1) LiAlH4 / ether
2) H2O
1) CH3CH2MgBr / ether
2) H3O+
1) NH3
2) H3O+
a)
b)
c)
d)
Chapter 15 Functional Derivatives of Carboxylic Acids
185
25. Which are the best conditions for the following reaction? (Sec. 15.9)
Fill in the Blank 1. The IUPAC name of the following compound is ______________________________. (Sec. 15.2)
O
O
2. The IUPAC name of the following compound is ______________________________. (Sec. 15.2)
N
O
3. The reagents that complete the following reaction are,
O
O
OH
O
(Sec. 15.4)
CH3CCH2COCH2CH3
OO
CH3CHCH2COCH2CH3
OOH
1) NaBH4 / ether
2) H2O
1) LiAlH4 / ether
2) H2O
1) CH3CH2MgBr / ether
2) H3O+
1) NH3
2) H3O+
a)
b)
c)
d)
Chapter 15 Functional Derivatives of Carboxylic Acids
186
4. The starting material that completes the following reaction is,
NH
N
O
(Sec. 15.6) 5. The reagents that complete the following reaction are,
O
Cl
O
O
(Sec. 15.5) 6. The major product that completes the following reaction is,
O
O MgBr
2) H+, H2O
1)
(Sec. 15.8) 7. The reagents that complete the following reaction are,
N
O
N
(Sec. 15.9) 8. The reagents that complete the following reaction are,
O
OHNH
O
(Sec. 15.4)
Chapter 15 Functional Derivatives of Carboxylic Acids
187
9. The major product that completes the following reaction is,
Cl
O
OH
(Sec. 15.5) 10. The major product that completes the following reaction is,
O
O O
H2O
(Sec. 15.4) True-False 1. The order of reactivity of the carboxylic acid derivatives with water is,
Cl
O
O
O O
OCH2CH3
O
NH2
O> > >
(Sec. 15.3) 2. The order of reactivity of the carboxylic acid derivatives with ammonia is,
Cl
O
O
O O
OCH2CH3
O
NH2
O> > >
(Sec. 15.3) 3. The name of the following compound is 3-methylbutanoyl 2-methylbutanoate. (Sec. 15.2)
O
O O
Chapter 15 Functional Derivatives of Carboxylic Acids
188
4. The structure for cyclohexanecarboxylic 2,2-dimethylpropanoic anhydride is,
O
O O
(Sec. 15.2) 5. The product of the reaction of 5-pentanolactam with aqueous acid and heat is 5-aminopentanoic acid. (Sec. 15.4) 6. The product of the reaction of 4-butanolactone with ethanol and acid is butanoic acid and diethylether. (Sec. 15.5) 7. The product of the reaction of propanamide with ethanol is ethyl propanoate. (Sec. 15.5) 8. Sodium borohydride reduces propanamide to propanamine. (Sec. 15.9) 9. Lithium aluminum hydride reduces 3-oxobutanoic acid to 4-hydroxy-2-butanone. (Sec. 15.9) 10. The proper mechanism for the reaction of acetyl chloride and water is shown below. (Sec. 15.3)
Cl
O
Cl
O
OH H
Cl
O
OH OH
O
H2O
+ Cl-
+
Chapter 15 Functional Derivatives of Carboxylic Acids
189
Answers Multiple Choice 1. a 2. c 3. d 4. c 5. a 6. d 7. c 8. d 9. b 10. d 11. c 12. a 13. d 14. d 15. b 16. b 17. a 18. b 19. b 20. d 21. a 22. b 23. a 24. b 25. a Fill in the Blank 1. E – 1-methylethyl 2-pentenoate or E – isopropyl 2-pentenoate 2. N,N-dimethyl cyclohexane carboxamide 3. H2O, H+ 4. As written,
Cl
O
O
O O
or
if heat is assumed,
OR
O
may also be correct
Chapter 15 Functional Derivatives of Carboxylic Acids
190
5.
OH
6.
OH
7. 1) LiAlH4, ether 2) H2O 8. H2O, H+, heat 9.
O
O
10.
OH
O
2
True-False 1. T 2. F 3. F 4. T 5. T 6. F 7. F 8. F 9. F 10. T
Chapter 16 Enolate Anions
191
Multiple Choice 1. What is the order of increasing acidity for these compounds (least acidic first)? (Sec. 16.2)
a) IV, III, II, I b) IV, II, III, I c) II, III, I, IV d) III, II, I, IV
2. What is the order of decreasing acidity for the indicated protons (most acidic first)? (Sec. 16.2)
a) I, II, III, IV b) III, IV, II, I c) II, I, III, IV d) IV, III, II, I
3. Which compound undergoes the fastest exchange of hydrogen for deuterium when treated with D2O and a trace of OD-? (Sec. 16.2)
CH3CH2OH CH3CCH3
O
CH3COCH3
O
CH3COH
O
I II III IV
CH3COCH2CH3
O
CH3CCH3
O
CH3CCH2COCH2CH3
O O
CH3CH2OH
I II III IV
O OH3C CH3
O
O
O
O
O O
a) b) c) d)
Chapter 16 Enolate Anions
192
4. Which are contributing resonance structures of the enolate formed by the treatment of butanone with base? (Sec. 16.2)
a) II, IV, V b) I, III, V c) II, IV, V d) I, III, IV
5. Which are the most important contributing structures for the enolate formed by the treatment of 2,4-pentanedione with base? (Sec. 16.2)
a) I, II b) II, III c) III, IV d) I, IV
O O OO O OOO
I II III IV
H2CC
O
CH2CH3 H3CC
O
CH2CH3 H3CC
O
C
H
CH3
H3CC
O
CH2CH2 H2CC
O
CH2CH3
I II III
IV V
Chapter 16 Enolate Anions
193
6. Which are the reactants for the aldol product shown? (Sec. 16.3)
7. Which is the product of the series of reactions? (Sec. 16.3)
O
CHCHCH2CH3
OH
CH3
OCH3CH2CHCH
CH3
O
CH3CHCH2CH
O
CH3
O
CH
O
CH3CH2CCH3
O
CH3CH2CH2CH
O
O
CH3
a) b)
c) d)
+
+
+
+
CH3CH2CH
OOH H3O
heatRhH2
CH3CH2CH2CHCH
CH3
O
CH3CH2CHCCH3
O
CH3
CH3CH2CH2CHCH2OH
CH3
a) b)
c) d)
C CCH
O
CH3H
CH3CH2
Chapter 16 Enolate Anions
194
8. Which is the major product of the following reaction? (Sec. 16.3)
9. Which of the following compounds can be used in an aldol self reaction to make a product with 5 or more carbon atoms? (Sec. 16.3)
I) ethanal II) propanone (acetone) III) benzaldehyde IV) acetophenone
a) I, II b) III, IV c) I, III d) II, IV
10. Which is the major product from the reaction of 1,6-cyclodecanedione with hot aqueous NaOH? (Sec. 16.3)
11. How many possible compounds are formed when acetone and ethanal are mixed in the presence of base? (Sec. 16.3)
a) 1 b) 2 c) 3 d) 4
HCCH2CH2CH2CH2CCH3
O O
Na OCH2CH3+
OH
OH Oa) b) c) d)
d)c)b)a)
O
CH3
O
CH
OCH3
CCH3
O
Chapter 16 Enolate Anions
195
12. How would you characterize this reaction forming fructose 1,6-bisphosphate? (Sec. 16.5)
a) aldol reaction b) substitution c) Claisen condensation d) Dieckmann Condensation
13. How many possible compounds are formed when ethyl propanoate and ethyl methanoate are mixed with sodium ethoxide? (Sec. 16.4)
a) 1 b) 2 c) 3 d) 4
14. Which pair of esters is most likely to provide a useful Claisen synthesis (Sec. 16.4)
a) ethyl propanoate and ethyl ethanoate b) ethyl benzoate and ethyl methanoate c) ethyl ethanoate and ethyl oxalate d) ethyl nicotinate and diethyl phthalate
15. Which is the major product formed in the following reaction? (Sec. 16.4)
CH2OPO32-
C O
CH2OH
CH2OPO32-
HC OH
HC O
CH2OPO32-
C O
CHO H
C OHH
C OHH
CH2OPO32-
+
CH3CH2OCCH2CH2CH2CH2CH2COCH2CH3
O ONaOCH2CH3 H3O
O
COCH2CH3
O
O
COCH2CH3
O
OOO
CCH3
O
a) b)
c) d)
Chapter 16 Enolate Anions
196
16. What is the major product of the following reaction? (Sec. 16.4)
17. What is the major product of the following reaction? (Sec. 16.4)
C C
H
COCH2CH3
O
CCH2
O
CCH
O
COCH2CH3
O
CCH2C
O O
a) b)
c) d)
CH2COCH2CH3
O
CH2COCH2CH3
O
NaOCH2CH3 H3O
O
CCH3
O
O
COCH2CH3
O
O
O
O
COCH2CH3
O
a) b)
c) d)
+1) NaOCH2CH3
2) H3O+CH2COCH2CH3
O
COCH2CH3
O
Chapter 16 Enolate Anions
197
18. Which compounds will undergo decarboxylation upon heating? (Sec. 16.4)
a) I, II b) II, III c) III, IV d) II, IV
19. Which is the major product of the following series of reactions? (Sec. 16.6)
O
O O O
+CH3CH2ONa
CH3CH2OH
NaOH, H2O HCl, H2O heat
O O O O O
O
O O
O
O O
O
a) b)
c) d)
CH3CH2OCCH2COCH2CH3
O O
CH3CH2CCH2COCH2CH3
O O
CH3CH2OCCH2COH
O O
HOCCH2COH
O O
I II
III IV
Chapter 16 Enolate Anions
198
20. Which is the product of the following series of reactions? (Sec. 16.4)
+heat
2) H3O
1) NaOH, heat
2) H3O
1) NaOCH2CH3
CH3CH2OC COCH2CH3
O O
CH3CH2COCH2CH3
O
+
21. Which ester is likely to undergo a Claisen condensation to give this product? (Sec. 16.4)
CH3CH2CH2CCHCOCH2CH3
O O
CH2CH3
a) ethyl 2-methylpropanoate b) ethyl butanoate c) butyl ethanoate d) 2-methylpropyl ethanoate
CH3CH2CCH2COH
O O
CH3CH2C COH
O O
CH3CH2CCH3
O
CH3CHCH
O
COH
O
a) b)
c) d)
Chapter 16 Enolate Anions
199
22. Which is the product of the reaction of ethyl 3-phenylpropanoate with 1) sodium ethoxide, 2) aqueous sodium hydroxide, 3) aqueous hydrochloric acid, and 4) heat? (Sec. 16.4)
23. The following synthesis will proceed by which reaction? (Sec. 16.5)
a) Claisen condensation b) Dieckmann condensation c) Aldol addition d) Aldol condensation reaction
24. Which is the major product of the following series of reactions? (Sec. 16.4)
CH3COH
OSOCl2 CH3CH2OH NaOCH2CH3
ethanolNaOH, heat heat1)
2) H3O+
CH2CCH2CH2
O
CH2CH2CCH
O
CH3
CH2CCH2
O
CH2CH2CCH2CH2
O
d)
c)
b)
a)
CH3CCH2COCH2CH3
O O O
O
CH3CCH3
O
CH3CH2OCCH2COCH2CH3
O Oa) b) c) d)
enzymecatalysis ++ CoASHCH3CCH2CSCoA
O O
CH3CSCoA
O
CH3CSCoA
O
Chapter 16 Enolate Anions
200
25. Which is the major product of the following series of reactions? (Sec. 16.4)
Fill in the Blank 1. The major product of the following reaction is,
O NaOH, H2O
2
(Sec. 16.3) 2. The starting material that completes the following reaction is,
H
O
H
O
+NaOH, H2O
(Sec. 16.3) 3. The starting material that completes the following reaction is,
H
O
NaOH, H2O
(Sec. 16.3)
SOCl2 CH3CH2OH NaOCH2CH3
ethanol, heatHOCCH2CH2CH2CH2CH2CCH3
O OH3O
d)c)b)a)
OH
CO
CH3
C
O
O
CH3
CH3
COCH2CH3
O
OH
CH3
COCH2CH3
O
Chapter 16 Enolate Anions
201
4. The major product of the following reaction is,
O
O O NaOH, H2O+
(Sec. 16.4) 5. The major product of the following reaction is,
OO
O
O
NaOH, H2O
(Sec. 16.4) 6. The major product of the following reaction is,
O
O
O
O
+NaOH, H2O
(Sec. 16.4) 7. The starting material that completes the following reaction is,
O O
O O
O O
O O
OH
+NaOH, H2O
(Sec. 16.6) 8. The major product of the following reaction is,
O
O+ CH3NH2
(Sec. 16.6)
Chapter 16 Enolate Anions
202
9. The major product of the following reaction is,
O
O O
O+1) NaOCH2CH3, ethanol
2) NaOH, H2O3) HCl, H2O4) heat
(Sec. 16.4) 10. The starting material that completes the following reaction is,
O
O OO
OO
+
1) NaOCH2CH3, ethanol
2) NaOH, H2O3) HCl, H2O4) heat
(Sec. 16.4, 16.6) True-False 1. The major enolate form of 2-pentanone is,
O
(Sec. 16.2) 2. The major enolate form of ethyl 3-oxobutanoate is,
O
O O
(Sec. 16.2) 3. The position of the most acidic hydrogen of the following compound is indicated by the arrow.
O
O O
(Sec. 16.2)
Chapter 16 Enolate Anions
203
4. The position of the most acidic hydrogen of the following compound is indicated by the arrow.
OH
O O
(Sec. 16.2) 5. The major product of the reaction of two moles of ethyl benzoate with sodium ethoxide is,
O
O O
(Sec. 16.4) 6. The major product of the reaction of 2,4-pentanedione and 3-buten-2-one with ethoxide followed by hydroxide, acid, and heat sequentially, is,
O O
(Sec. 16.3) 7. 1-Cyclohexenecarbaldehyde can be produced from the following starting material and base.
HH
O
O
(Sec. 16.3) 8. The Michael addition of dimethylamine and 3-buten-2-one produces the following product,
O
N
(Sec. 16.6) 9. The condensation of acetoacetyl-CoA with acetyl-CoA is an Aldol reaction. (Sec. 16.5) 10. The self condensation of Acetyl-CoA to Acetoacetyl-CoA is a Claisen reaction. (Sec. 16.5)
Chapter 16 Enolate Anions
204
Answers Multiple Choice 1. d 2. b 3. d 4. b 5. b 6. a 7. c 8. b 9. d 10. d 11. d 12. a 13. b 14. c 15. a 16. c 17. b 18. c 19. a 20. b 21. b 22. d 23. a 24. c 25. c Fill in the Blank 1.
O
OH
O
or
2.
H
O
3.
H H
O O
Chapter 16 Enolate Anions
205
4. O O
5.
O
O O
6.
O
OO
7.
O
H
8.
O
O
N
H 9.
O
10.
O
O
True-False 1. F 2. F
Chapter 16 Enolate Anions
206
3. T 4. F 5. F 6. F 7. F 8. T 9. T 10. T
Chapter 17 Organic Polymer Chemistry
207
Multiple Choice
1. Which of the following are polymer architectures? (Sec. 17.2)
I) linear
II) tetrahedral
III) star
IV) ladder
V) forked
a) II, III, IV
b) III, IV, V
c) I, III, IV
d) I, II, IV
2. Which terms are correctly matched to their definitions? (Sec. 17.2)
I) Plastic – a long chain molecule synthesized by linking together many single parts.
II) Polymer – can be molded when hot and retains its shape when cooled.
III) Thermoplastic - can be molded when hot and retains its shape when cooled.
IV) Thermosetting plastic – can be molded when first prepared, but hardens irreversibly when
cooled.
a) III, IV
b) II, III
c) I, II
d) I, IV
3. Determine the repeat unit for the following polymer. (Sec. 17.1, 17.5, 17.6)
CH2CH O
CH3
CH2CH O
CH3
CH2CH O
CH3
CH2CH
CH3
O CH2CH
CH3
O CH2CH O
CH3
CH
CH3
O CH2CH
CH3
a) b)
c) d)
n n
n n
Chapter 17 Organic Polymer Chemistry
208
4. Determine the repeat unit for the following polymer. (Sec. 17.1, 17.5, 17.6)
5. Which characteristics are found in polymers with high degrees of crystallinity? (Sec. 17.4)
I) regular, compact structures
II) high Tm
III) weak intermolecular forces
IV) elasticity
a) I, III
b) I, II
c) III, IV
d) II, IV
6. Which characteristics are found in polymers with low degrees of crystallinity? (Sec. 17.4)
I) large molecular side groups
II) high Tm
III) strong intermolecular forces
IV) elasticity
a) I, III
b) II, III
c) III, IV
d) I, IV
7. Which terms are matched correctly with their definitions? (Sec. 17.4)
I) Crystalline domain – order regions in the solid state of a polymer.
II) Amorphous domain – disordered regions in the solid state of a polymer.
III) Melt transition temperature – temperature at which a polymer undergoes the transition from
hard to rubbery state.
IV) Glass transition temperature – temperature at which glass polymers melt.
a) II, III
b) III, IV
c) I, IV
d) I, II
O CH2CH2 O O CH2CH2 OOCH2CH2 O CH2CH2
d)c)
b)a)
nn
nn
CH2CH2 O O CH2CH2O O CH2CH2 O O
O CH2CH2 OO CH2CH2 O
Chapter 17 Organic Polymer Chemistry
209
8. Which polymers are correctly classified? (Sec. 17.5)
a) II, III
b) III, IV
c) I, IV
d) I, II
9. Which polymers are correctly classified? (Sec. 17.5)
I
polycarbonyl
polyurethane
n
CH3
NCOCH2CH2CH2OCN
O O
H H
polyether
polycarbonate
IVIII
IIInn
C
O
OO CH2
CCH2CH2CH2CH2COCH2CH2O
O O
NCH2CH2CH2CH2CH2C
H
O
I
a) I, III
b) II, III
c) III, IV
d) II, IV
polyester
polyurethanepolycarbonate
polyamide
IV
IIIII
I
n
nn
n
C
O
OO C
CH3
CH3
C COCH2CH2O
O O
NCH2CH2CH2CH2CH2C
H
O
CCH2CH2CH2CH2CNCH2CH2CH2CH2CH2CH2N
O O
H H
Chapter 17 Organic Polymer Chemistry
210
10. Which pair of compounds would react to form the polymer shown? (Sec. 17.5)
11. Which pair of compounds would react to form the polymer shown? (Sec. 17.5)
C
O
OO C
CH3
CH3
CCH2CH2CH2CH2CNCH2CH2CH2CH2CH2CH2N
O O
H H
C
O
OHC
O
HO HOCH2CH2OH
C
CH3
CH3
Na O O Na C
O
ClCl
HOCCH2CH2CH2CH2COH
O O
H2NCH2CH2CH2CH2CH2CH2NH2
C
CH3
CH3
Na O O Na H2C C
O
CH2Cl
H
H2NCH2CH2NH2
+
+
+
++
d)
c)
b)
a)
a)
b)
c)
d) ++
+
+
+
H2NCH2CH2NH2H2C C
O
CH2Cl
HC
CH3
CH3
Na O O Na
H2NCH2CH2CH2CH2CH2CH2NH2HOCCH2CH2CH2CH2COH
O O
C
O
ClCl
HOCH2CH2OHHOCCH2CH2CH2CH2COH
O O
H2NCH2CH2CH2CH2CH2CH2NH2
Chapter 17 Organic Polymer Chemistry
211
12. Which pair of compounds would react to form the polymer shown? (Sec. 17.5)
13. Which compound would react to form the polymer shown? (Sec. 17.6)
14. Which is not a step in the mechanism of a chain growth polymerization? (Sec. 17.6)
a) initiation
b) propagation
c) proliferation
d) termination
15. Which classification best describes the mechanism of step growth polymerization? (Sec. 17.5)
a) nucleophilic acyl addition
b) nucleophilic acyl substitution
c) electrophilic addition
d) radical substitution
C
O
OHC
O
HO HOCH2CH2OH
C
CH3
CH3
Na O O Na C
O
ClCl
HOCCH2CH2CH2CH2COH
O O
H2NCH2CH2CH2CH2CH2CH2NH2
C
CH3
CH3
Na O O Na H2C C
O
CH2Cl
H
H2NCH2CH2NH2
+
+
+
++
d)
c)
b)
a)
C
CH3
CH3
O O
OH OH
N
H
N
Hn
n
OHClO
a) b) c) d)
Chapter 17 Organic Polymer Chemistry
212
16. Which statements are true describing the Ziegler-Natta process? (Sec. 17.6)
I) the process yields low density polyethylene
II) the process involves radicals
III) the process uses an alkytitanium catalyst
IV) the process yields polyethylene 3 to 10 times stronger than other methods
a) I, II
b) II, IV
c) II, III
d) III, IV
17. Which polymers will be brittle at 0° C? (Sec. 17.4)
I) PVC, Tg = 83° C
II) PVA, Tg = 200° C
III) teflon, Tg = -80° C
IV) polypropylene, Tg = -100° C
a) III, IV
b) II, III
c) I, II
d) II, IV
18. Which polymers will be elastic at 0° C? (Sec. 17.4)
I) PVC, Tg = 83° C
II) PVA, Tg = 200° C
III) teflon, Tg = -80° C
IV) polypropylene, Tg = -100° C
a) III, IV
b) II, III
c) I, II
d) II, IV
19. Which polymers will be strongest? (Sec. 17.4)
a) PET 0% crystallinity
b) PET 20% crystallinity
c) PET 35% crystallinity
d) PET 55% crystallinity
20. Which polymers will be the most elastic? (Sec. 17.4)
a) PET 0% crystallinity
b) PET 20% crystallinity
c) PET 35% crystallinity
d) PET 55% crystallinity
Chapter 17 Organic Polymer Chemistry
213
21. Which polymers are step-growth polymers? (Sec. 17.5)
I) nylon
II) HDPE
III) Teflon
IV) PET
a) I, II
b) II, III
c) I, IV
d) III, IV
22. Which polymers are chain-growth polymers? (Sec. 17.6)
I) nylon
II) HDPE
III) Teflon
IV) PET
a) I, II
b) II, III
c) I, IV
d) III, IV
23. Which polymers are step-growth polymers? (Sec. 17.5)
I) Kevlar
II) Mylar
III) PVC
IV) Lucite
a) I, II
b) II, III
c) I, IV
d) III, IV
24. Which polymers are chain-growth polymers? (Sec. 17.6)
I) Kevlar
II) Mylar
III) PVC
IV) Lucite
a) I, II
b) II, III
c) I, IV
d) III, IV
Chapter 17 Organic Polymer Chemistry
214
25. Which polymers are correctly matched to their primary use? (Sec. 17.5, 17.6)
I) Kevlar and containers
II) Polymethylmethacrylate and Plexiglas
III) Polytetrafluoroethylene and nonstick coatings
IV) PET and bulletproof vests
a) I, III
b) II, III
c) II, IV
d) III, IV
Fill in the Blank
1. The repeat unit of polyacrylonitrile is,
CH2
CH
CH2
CN
CH
CN
CH2
CH
CN
CH2
CH
CN
n
(Sec. 17.6)
2. The repeat unit of polymethylacrylate is,
CH2
CH
CH2
CH
CH2
CH
CH2
CH
n
O
OCH3
O O
OCH3
O
OCH3
OCH3
(Sec. 17.6)
Chapter 17 Organic Polymer Chemistry
215
3. The polymer (Nylon 612) synthesized from the following monomers is,
CH2
CH2
CH2
CH2
CH2
CH2
NH2
NH2
and
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
C
C
O
OH
O
OH
(Sec. 17.5)
4. The polymer (PEN) synthesized from the following monomer is
C
O
CH3O
C
O
OCH3
and OH CH
2CH
2OH
(Sec. 17.5)
5. The monomers used to synthesize Nomex are,
O O
NH
NH n
(Sec. 17.5)
and
Chapter 17 Organic Polymer Chemistry
216
6. The monomers used to synthesize the following polyurethane are,
CH2
NH
O
NH
O
O CH2
CH2
On
(Sec. 17.5)
and
7. Complete the mechanism for radical chain propagation begun below. (Sec. 17.6)
Cl Cl
Cl
InIn Cl
..
8. The label of the following step of radical chain polymerization is __________________________.
Cl
Cl
Cl
ClR
Cl
Cl
Cl R
Cl
. .
(Sec. 17.6)
9. A carbonate, which forms the backbone of polycarbonates, has the following structure,
(Sec. 17.5)
Chapter 17 Organic Polymer Chemistry
217
10. A diepoxide, which forms the backbone of epoxy resins, has the following structure,
(Sec. 17.5)
True-False
1. The glass transition temperature (Tg) must be low for an elastomer to maintain its properties. (Sec. 17.4)
2. The opaquety of a crystalline polymer correlates to the Tm. (Sec. 17.4)
3. The polymer synthesized from the following monomer is,
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
n
(Sec. 17.6)
4. A polymer synthesized from the following monomers could have the form,
CH2
CH2
CH2
CH
CH2
CH2
CH CH3
CH3
and
(Sec. 17.6)
n
Chapter 17 Organic Polymer Chemistry
218
5. A polymer synthesized from the following monomers could have the form,
CH2
C
CN
H
CH2
O
CH3
CH3
O
and
(Sec. 17.6)
CH2
CH
CH2CH
CH2
CH
CH2
CH
n
O O
OCH3
OCH3
CN CN
6. Radical chain growth polymers tend to form head to head bonds between carbon one of one monomer and
carbon one of another monomer. (Sec. 17.6)
7. Branching of polyethylene, due to a chain transfer reaction, produces low density polyethylene (LDPE).
(Sec. 17.6)
8. The Zeigler-Natta process yields low density polyethylene (LDPE). (Sec. 17.6)
9. A polymer with a melt transition temperature (Tm) of 200° C is stronger than a polymer with a Tm of 150° C.
(Sec. 17.4)
10. An elastomer with a glass transition temperature (Tg) of 25° C will lose its elasticity below 25° C. (Sec. 17.4)
Chapter 17 Organic Polymer Chemistry
219
Answers
Multiple Choice
1. c
2. a
3. a
4. b
5. b
6. d
7. d
8. c
9. c
10. c
11. b
12. d
13. a
14. c
15. b
16. d
17. c
18. a
19. d
20. a
21. c
22. b
23. a
24. d
25. b
Fill in the Blank
1.
CN
2.
OCH3O
3.
*
O
O
NH
NH
*n
4.
O
* OO
O *n
Chapter 17 Organic Polymer Chemistry
220
5.
O
OH OH
ONH2 NH2
and
6.
CH2NCO N C O OH OHand
7.
Cl Cl
Cl
InIn Cl
.
8. Termination
9.
O
RO OR
10.
OOR
True-False
1. T
2. T
3. F
4. T
5. F
6. F
7. T
8. F
9. T
10. T
Chapter 18 Carbohydrates
221
Multiple Choice 1. Which sugars and classifications are correctly matched? (Sec. 18.2)
a) III, V b) II, III, IV c) I, III d) III, IV, V
2. Which sugars and classifications are correctly matched? (Sec. 18.2)
I) D-Glucose and aldohexose II) D-Galactose and aldopentose III) D-Ribose and ketopentose IV) D-Fructose and ketohexose V) D-Mannose and ketohexose
a) I, III, V b) I, IV c) III, IV, V d) II, III
3. Which is the correct structure for D-glyceraldehyde? (Sec. 18.2)
CH2OH
OHH
OHH
H OH
CHO
CH2OH
HO H
OHH
HHO
H OH
CHO
CH2OH
HHO
OHH
CHO
CH2OH
HO H
OHH
HHO
O
CH2OH
CH2OH
OHH
OHH
O
CH2OH
aldohexoseI
aldotetroseII
aldohexoseIII
ketotetroseIV
ketopentoseV
C
CHO
CH2OH
HH C
CHO
CH2OH
HHO C
CH2OH
CH2OH
OHH C
CHO
CH2OH
OHH
a) b) c) d)
Chapter 18 Carbohydrates
222
4. Which monosaccharides have the D configuration? (Sec. 18.2)
a) I, IV, V b) II, III, VI c) IV, V d) IV, VI
5. What is the relationship between the following compounds? (Sec. 18.2)
a) enantiomers b) anomers c) meso compounds d) diastereomers
6. What is the relationship between the following compounds? (Sec. 18.2)
a) anomers b) diastereomers c) enantiomers d) identical structures
CHO
OHH
HHO
H OH
CH2OH
CH2OH
HHO
OHH
HO H
CHO
CH2OH
HHO
OHH
H OH
CHO
CH2OH
OHH
OHH
H OH
CHO
CH2OH
OHH
OHH
HO H
CHO
CHO
HHO
OHH
H OH
CH2OH
I II III IV V VI
CH2OH
HHO
OHH
H OH
CHO
CH2OH
OHH
OHH
H OH
CHO
CH2OH
HHO
HHO
CHO
CH2OH
OHH
OHH
CHO
Chapter 18 Carbohydrates
223
7. What is the relationship between the following compounds? (Sec. 18.2, 18.3)
a) anomers b) meso compounds c) enantiomers d) identical structures
8. The Fischer projection for L-idose corresponds to which Haworth projection? (Sec. 18.3)
OH
H
H
OHOH
HOH
H
H
CH2OHO OH
H
H
OHOH
HOH
H
CH2OH
HO
H
OH
OH
HH
OHH
OH
CH2OH
HO OH
H
H
OHH
OHOH
H
H
CH2OHO
a) b)
c) d)
H
OH
H
OHH
OHH
OH
CH2OH
HOH
OH
OH
HH
OHH
OHH
OCH2OH
CH2OH
HO H
OHH
HHO
H OH
CHO
Chapter 18 Carbohydrates
224
9. Which is the correct structure for D-D-glucopyranose? (Sec. 18.2, 18.3)
10. How many stereocenters are there in a 2-ketohexose? (Sec. 18.2)
a) 2 b) 3 c) 8 d) 16
11. Which of the labeled bonds is a glycosidic bond? (Sec. 18.4)
12. Which of the labeled atoms is the anomeric carbon? (Sec. 18.3)
O
OHOHHO
HOCH2OH
CH2OH
H OH
OHH
HHO
H OH
CHO
OH OHOH
OH
CH2OHO
C
C3H7O3
CH2OH
OHH
a) b) c) d)
OH
OCH3
OH
OH
CH2OHO
a)
b) c)
d)
OH
OCH3
OH
OH
CH2OHO
a)
b)c)
d)
Chapter 18 Carbohydrates
225
13. Which reagents could be used to convert galactose to galactitol? (Sec. 18.4)
I) NaBH4 / H2O II) Tollen’s solution III) Benedict’s solution IV) Ni / H2
a) I, II b) II, III c) III, IV d) I, IV
14. Which reagents could be used to convert galactose to galacturonic acid? (Sec. 18.4)
I) NaBH4 / H2O II) Tollen’s solution III) Benedict’s solution IV) Ni / H2
a) I, II b) II, III c) III, IV d) I, IV
15. Which compounds and functional types are correctly matched? (Sec. 18.4)
a) I, IV b) I, II c) III, IV d) II, III
O
OCH3OHHO
HOCH2OH
CH2OH
H OH
OHH
HHO
H
COH
OH
O
OH
OH
NH2
OH
CH2OHO
CH2OH
H OH
OHH
HHO
H
CH2OH
OH
alditolI
aldonic acidII
amino sugarIII
glycosideIV
Chapter 18 Carbohydrates
226
16. Which are reducing sugars? (Sec. 18.4)
I) lactose II) sucrose III) glucose IV) fructose V) galactose
a) I, II, III b) I, III, IV, V c) II, III, IV, V d) III, IV, V
17. Which are disaccharides? (Sec. 18.7)
I) sucrose II) glucose III) maltose IV) lactose V) galactose
a) II, IV, V b) I, II, III c) III, IV, V d) I, III, IV
18. Which will reduction of D-fructose with NaBH4 yield? (Sec. 18.4)
a) a single chiral alditol b) a pair of enantiomeric alditols c) a meso compound d) two diastereomers
CH2OH
H OH
OHH
HHO
O
CH2OH
Chapter 18 Carbohydrates
227
19. Two sugars give identical products when treated with NaBH4. Which of the following are possible structures for the sugars? (Sec. 18.4)
a) I, II b) I, III c) III, IV d) II, IV
20. Which sugars are monosaccharides? (Sec. 18.2)
I) mannose II) maltose III) ribose IV) lactose V) glucose
a) I, II, III b) II, III, IV c) II, IV, V d) I, III, V
21. Cellulose, starch, and glycogen are polysaccharides that contain which sugar? (Sec. 18.8)
a) sucrose b) glucose c) fructose d) lactose
22. Which sugars are reducing sugars? (Sec. 18.4)
I) sucrose II) maltose III) lactose IV) fructose
a) I, II, III b) II, III, IV c) I, III, IV d) I, II, IV
CH2OH
OHH
OHH
CHO
CH2OH
HHO
HHO
CHO
CH2OH
OHH
HHO
CHO
CH2OH
HHO
OHH
CHO
I II III IV
Chapter 18 Carbohydrates
228
23. Which of the statements about sucrose is false? (Sec. 18.7)
a) The linkage between anomeric carbon atoms is 1,4’. b) It is the most abundant disaccharide. c) It cannot reduce Tollens’ reagent. d) It is a disaccharide composed of glucose and fructose.
24. Which statements about the following sugar are true? (Sec. 18.7)
I) It is a reducing sugar. II) It will undergo mutarotation. III) The linkage is 1,1’. IV) It is composed of two units of D-glucose.
a) I, II b) II, III c) III, IV d) I, IV
25. Which statements about L-ascorbic acid are true? (Sec. 18.6)
I) L-ascorbic acid is synthesized from D-glucose. II) Humans enzymatically synthesize L-ascorbic acid. III) L-ascorbic acid is easily oxidized to the diketone, L-dehydroascorbic acid. IV) L-dehydroascorbic acid is not physiologically active.
a) I, II b) II, IV c) I, III d) III, IV
O
O OOHHO
HOCH2OH
CH2OHOH
OHHO
Chapter 18 Carbohydrates
229
Fill in the Blank 1. Complete the following reaction by providing the product of the reaction. (Sec. 18.4)
CHO
H OH
OH HHOH
CH2OH
OHH
enzyme catalyzedoxidation
2. Complete the following reaction by providing the product of the reaction. (Sec. 18.4)
CHO
OH H
OH HOHH
CH2OH
OHH
Tollen's Reagent
3. Complete the following reaction by providing the reagent needed. (Sec. 18.4)
CHO
H OH
OH HOHH
CH2OHOHH
CH2OH
H OH
OH HOHH
CH2OHOHH
4. Complete the following reaction by providing the reagent needed. (Sec. 18.4)
OCH2OH
OH
OHOH
OHH
H
H
HO
CH2OHOCH3
OHOH
OHH
H
H
H
Chapter 18 Carbohydrates
230
5. Complete the following reaction by providing the product of the reaction. (Sec. 18.4)
O
OHOHH
CH2OH OH
H
H H
N
NH
O
NH2
6. The E-pyranose form of D-Galactose is,
CHO
H OH
OH HHOH
CH2OHOHH
(Sec. 18.3) 7. The D-furanose form of D-Fructose is,
CH2OH
O
OH H
OHH
CH2OH
OHH
(Sec. 18.3) 8. Complete the following reaction by providing the products of the reaction. (Sec. 18.3)
O OHOH
OH
OH
OH aqueoussolution
+
9. The structure of cellulose is a(n) _________________ polymer of glucose. (Sec. 18.8) 10. The structure of amylopectin is a(n) __________________ polymer of glucose. (Sec. 18.8)
Chapter 18 Carbohydrates
231
True-False 1. The structure of D-D-Mannose is,
OCH2OH
HH
OHH
OH
H
OHH
OH
(Sec. 18.3) 2. The structure of E-D-Galacuronic acid is,
OH
OH
HH
OH
OH
HH
OHCOOH
(Sec. 18.4) 3. The structure of D-Gluconic acid is,
H OH
OH HOHH
CH2OHOHH
COOH
(Sec. 18.4) 4. The structure of D-Mannitol is,
OH H
OH HOHH
OHH
COOH
COOH (Sec. 18.4) 5. D-Glucosamine, D-Mannosamine, and D-Galactosamine are C-2 stereoisomers of each other. (Sec. 18.4) 6. Glycogen is a branched component of starch. (Sec. 18.8) 7. Amylose and amylopectin are unbranched components of starch. (Sec. 18.8)
Chapter 18 Carbohydrates
232
8. Glucose, Galactose, and Fructose are aldohexoses. (Sec. 18.2) 9. D-D-glucopyranose is a hemi-acetal. (Sec. 18.3) 10. Sucrose is an acetal. (Sec. 18.7)
Chapter 18 Carbohydrates
233
Answers Multiple Choice 1. a 2. b 3. d 4. c 5. d 6. c 7. a 8. c 9. c 10. c 11. d 12. c 13. d 14. b 15. d 16. b 17. d 18. d 19. a 20. d 21. b 22. b 23. a 24. c 25. c Fill in the Blank 1.
CHO
H OH
OH H
HOH
OHHCOOH
2.
OH H
OH HOHH
CH2OHOHH
COOH
3. NaBH4/H2O or H2 and metal catalyst
Chapter 18 Carbohydrates
234
4. CH3OH / H+ 5.
N
N
O
OHOHH
CH2OH
H
H H
NH2
O
6.
OOH
OH
OHOHCH2OH
7.
OCH2OH
OH
OH
OH
CH2OH
8.
O OHOH
OH
OH
OHO
OH
OH
OH
OHOH
+
9. linear 10. branched True-False 1. F 2. T 3. T 4. F 5. F 6. F 7. F 8. F 9. T 10. T
Chapter 19 Amino Acids and Proteins
235
Multiple Choice 1. Which amino acid has a nonpolar side chain? (Sec. 19.2)
2. Which amino acid has an acidic side chain? (Sec. 19.2)
H2NCCH2CH2CHCO
O O
NH3
CH3SCH2CH2CHCO
O
NH3
N
N
H
CH2CHCO
O
NH3
OH
CH2CHCO
O
NH3
a) b)
c) d)
H2NCCH2CH2CHCO
O O
NH3
CH3SCH2CH2CHCO
O
NH3
N
N
H
CH2CHCO
O
NH3
OH
CH2CHCO
O
NH3
a) b)
c) d)
Chapter 19 Amino Acids and Proteins
236
3. Which amino acid has a basic side chain? (Sec. 19.2)
4. Which molecules are zwitterions? (Sec. 19.2)
a) I, III b) II, III c) III, IV d) I, IV
5. Which describes the isoelectric point of an amino acid? (Sec. 19.3)
a) The degree of ionization of the amino acid at pH 7. b) The pH at which there is no net charge for the amino acid. c) The pH at which the ionized form predominates. d) The pH at which the amino acid is present as the dipolar ion.
H2NCCH2CH2CHCO
O O
NH3
CH3SCH2CH2CHCO
O
NH3
a) b)
c) d)
HSCH2CHCO
O
NH3
H2NCNHCH2CH2CH2CHCO
O
NH3
NH2
H2NCCH2CH2CHCO
O O
NH3
HSCH2CHCOH
O
NH3
H2NCNHCH2CH2CH2CHCO
O
NH3
NH2
NHH
CO
O
I II
III IV
Chapter 19 Amino Acids and Proteins
237
6. Which is the order of increasing acidity for the indicated carboxyl groups (least first)? (Sec. 19.3)
a) I, II, III b) II, III, I c) III, II, I d) I, III, II
7. Which is the order of increasing basicity for the indicated amino groups (least first)? (Sec. 19.3)
a) I, II, III b) II, III, I c) III, II, I d) I, III, II
8. Tyrosine has an isoelectric point of 5.63. What charge does tyrosine have at pH 7 and which electrode does it migrate to during electrophoresis? (Sec. 19.3)
a) negative, anode b) positive, cathode c) negative, cathode d) positive, anode
9. Lysine has an isoelectric point of 9.74. What charge does tyrosine have at pH 7 and which electrode does it migrate to during electrophoresis? (Sec. 19.3)
a) negative, anode b) positive, cathode c) negative, cathode d) positive, anode
CH3CH2NH2
HN CNH2
NHCH2CH2CH2CHCOH
NH2
O
I
II
III
IIIIII
CH3CNCH2COH
O
H
O
H3NCH2COH
O
CH3COH
O
Chapter 19 Amino Acids and Proteins
238
10. Aspartic acid has an isoelectric point of 2.98. At which pH would the predominate form of aspartic acid in solution migrate toward the negative electrode during electrophoresis? (Sec. 19.3)
a) 1 b) 2.98 c) 4 d) 7
11. Arginine has an isoelectric point of 10.76. At which pH would the predominate form of arginine in solution migrate toward the positive terminal during electrophoresis? (Sec. 19.3)
a) 5 b) 7 c) 10.76 d) 12
12. Isoleucine has pka values of 2.32 (-COOH) and 9.76 (-NH3
+). Which is isoleucine’s isoelectric point? (Sec. 19.3)
a) 3.08 b) 7.64 c) 6.04 d) 9.74
13. Glutamic acid has an isoelectric point of 3.08. At which pH is the cationic form in greatest concentration? (Sec. 19.3)
a) 2 b) 3.2 c) 5.6 d) 9.7
14. Which is the order of increasing mobility of the molecule toward the cathode (least first)? (Sec. 19.3)
a) III, I, II, IV b) I, III, II, IV c) IV, II, I, III d) III, IV, I, II
IVIII
III
H2NCCH2CH2CHCO
O O
NH2
H2NCNHCH2CH2CH2CHCOH
O
NH3
NH2
H2NCCH2CH2CHCO
O O
NH3
H2NCNHCH2CH2CH2CHCO
O
NH3
NH2
Chapter 19 Amino Acids and Proteins
239
15. Which is the predominate form of lysine in blood plasma at pH 7.4? (Sec. 19.3)
16. Which is the charge on lysine at pH 11? (Sec. 19.3)
a) 0 b) +1 c) –1 d) +2
17. Which is the charge of lysine at pH 2? (Sec. 19.3)
a) 0 b) +1 c) –1 d) +2
18. Which is the structure of the pentapeptide that gave lys-leu-phe on reaction with cyanogen bromide, and gave fragments met-lys, leu-phe, and arg on reaction with trypsin. (Sec. 19.5)
a) arg-met-phen-leu-lys b) lys-leu-phe-arg-met c) arg-met-lys-leu-phe d) met-arg-lys-leu-phe
19. A polypeptide gave the following proportions of amino acids upon hydrolysis: ala (1), gly (1), ile (2), phe (2), ser (1), tyr (2). Edman degradation yields tyrosine phenylthiohydantoin. Partial hydrolysis of the peptide gave a mixture of smaller peptides including: ala-gly, gly-tyr, ile-ile, phe-ile, ser-phe, tyr-ser, tyr-phe, ile-ala. Which is the C-terminal amino acid in the original peptide? (Sec. 19.5)
a) tyr b) ser c) phe d) ile
H3NCH2CH2CH2CH2CHCOH
O
NH3
H2NCH2CH2CH2CH2CHCO
O
NH2
H3NCH2CH2CH2CH2CHCO
O
NH2
H3NCH2CH2CH2CH2CHCO
O
NH3
a) b)
c) d)
Chapter 19 Amino Acids and Proteins
240
20. A penta-peptide has the following proportions of amino acids: gly (1), leu (1), val (1), phe (2). Treatment of the pentapeptide with chymotrypsin gave the following fragments: gly-val, leu, phe. Which is the structure of the penta-peptide? (Sec. 19.5)
a) phe-phe-gly-val-leu b) gly-val-phe-leu-phe c) leu-gly-val-phe-phe d) phe-leu-gly-val-phe
21. Which is the chemical structure of the tripeptide glutathione (glu-cys-gly)? (Sec. 19.5)
22. Which characteristics are correct for a peptide bond in a polypeptide? (Sec. 19.4)
I) planar II) cis III) trans IV) tetrahedral
a) I, II b) I, III c) II, IV d) III, IV
23. Which are true describing the secondary structure of a protein that is an D-helix? (Sec. 19.6)
I) The helix is coiled counterclockwise. II) The N-H bond and the C=O bond point outward. III) Hydrogen bonding is between groups 4 amino acid units apart. IV) The coil has 3.6 amino acids per turn.
a) I, II b) I, III c) II, IV d) III, IV
OCCH2CH2CHCNHCHCNHCH2CO
O O
NH3
O
CH2SH
OH3NCHCH2CH2CNHCHCNHCH2CO
OO
CO
O
O
CH2SH
H3NCH2CNHCHCNHCHCH2CH2CO
OOO
CH2SH CO
O
H3NCHCNHCHCNHCH2CO
O
CH2SH
O
CH2CH2CO
O
O
a) b)
c) d)
Chapter 19 Amino Acids and Proteins
241
24. The secondary structure of proteins depends primarily on which property of amino acids? (Sec. 19.6)
a) disulfide bonds b) hydrogen bonds c) amide bonds d) polar side chains
25. The tertiary structure of proteins depends primarily on which property of amino acids? (Sec. 19.6)
I) disulfide bonds II) hydrogen bonds III) amide bonds VI) polar side chains
a) III, IV b) I, VI c) II, III d) I, II Fill in the Blank 1. The isoelectric point of proline is ______________. (Sec. 19.3) pKa (COOH) = 2.00, pKa (NH3
+) = 10.60 2. The isoelectric point of cysteine is ______________. (Sec. 19.3) pKa (COOH) = 2.05, pKa (NH3
+) = 10.25, pKa (SH) = 8.00 3. The structure of a common amino acid with a polar side chain is
(Sec. 19.2) 4. The structure of a common amino acid with an acidic side chain is
(Sec. 19.2)
Chapter 19 Amino Acids and Proteins
242
5. The structure of a common amino acid with a basic side chain is
(Sec. 19.2) 6. The structure of the tripeptide Met-Ile-Pro is
(Sec. 19.5) 7. The structure of the tripeptide Glu-Gly-Phe is
(Sec. 19.5) 8. The result of the reaction of Asp-Val-Met-Leu-His with cyanogens bromide is _______________________. (Sec. 19.5) 9. The result of the reaction of the hydrolysis of Ala-Phe-Leu-Tyr-Leu-Pro with chymotrypsin is __________________________. (Sec. 19.5) 10. The result of the reaction of the hydrolysis of Leu-Ile-Lys-Cys-Val-Asn-Gln-Tyr with trypsin is __________________________. (Sec. 19.5) True-False 1. The isoelectric point of Glycine is 6.06 (pKa (COOH) = 2.35, pKa (NH3
+) = 9.78). (Sec. 19.3) 2. At pH 7.05 lysine (pI = 9.74) will migrate toward the positive electrode during electrophoresis. (Sec. 19.3) 3. Asparagine is an amino acid with an acidic side chain. (Sec. 19.2) 4. Arginine is an amino acid with a basic side chain. (Sec. 19.2)
Chapter 19 Amino Acids and Proteins
243
5. The sequence of an octa-peptide can be deduced from the following experimental results as Cys-Asn-Met-Tyr-Val-Phe-Lys-Pro. (Sec. 19.5) Edman degradation Cys Hydrolysis catalyzed by Trypsin Cys, Asn, Met, Tyr, Val, Phe, Lys Pro Hydrolysis catalyzed by Chymotrypsin Cys, Asn, Met, Tyr Val, Phe Lys, Pro Treatment with Cyanogen Bromide Cys, Asn, Met Tyr, Val, Phe, Lys, Pro 6. The sequence of a hepta-peptide can be deduced from the following experimental results as Thr-Tyr-Cys-Gln-Arg-Trp-His (Sec. 19.5) Edman degradation Thr Hydrolysis catalyzed by Trypsin Thr, Tyr, Cys, Gln, Arg Trp, His Hydrolysis catalyzed by Chymotrypsin Thr, Tyr Cys, Gln, Arg, Trp His 7. The sequence of a deca-peptide can be deduced from the following experimental results as Leu-Met-Ser-Thr-Trp-His-Phe-Asp-Lys-Glu. (Sec. 19.5) Edman degradation Leu Hydrolysis catalyzed by Trypsin Leu, Met, Ser, Thr, Trp, His, Phe, Asp, Lys Glu Hydrolysis catalyzed by Chymotrypsin Leu, Met, Ser, Thr, Trp His, Phe Asp, Lys, Glu Treatment with Cyanogen Bromide Leu, Met Ser, Thr, Trp, His, Phe, Asp, Lys, Glu 8. D-Helix and E-sheet are examples of protein secondary structure. (Sec. 19.6) 9. A major stabilizing factor of protein tertiary structure is disulfide linkages. (Sec. 19.6) 10. The major stabilizing factor of the quaternary protein structure is hydrogen bonding. (Sec. 19.6)
Chapter 19 Amino Acids and Proteins
244
Answers Multiple Choice 1. b 2. a 3. d 4. c 5. b 6. d 7. b 8. a 9. b 10. a 11. d 12. c 13. a 14. c 15. d 16. c 17. d 18. c 19. c 20. b 21. a 22. b 23. d 24. b 25. d Fill in the Blank 1. 6.30 2. 5.02 3.
O
ONH3
OH O
ONH3
OH
O
ONH3
O
NH2
O
ONH3
O
NH2
+ +
+ +
Chapter 19 Amino Acids and Proteins
245
4. O
ONH3
SH
O
ONH3
O
O
O
ONH3
O
O
O
ONH3
OH+ +
+ + 5.
O
ONH3
H3N
NNH
O
ONH3
O
ONH3
NH
NH2
NH2
+
+
+
+
+
6.
N
O
NHNH3
O
O
O
SCH3
+
Chapter 19 Amino Acids and Proteins
246
7.
NH
O
NHNH3
O
O
O
OO
HH
+
8. Asp-Val-Met, Leu-His 9. Ala-Phe, Leu-Tyr, Leu-Pro 10. Leu-Ile-Lys, Cys-Val-Asn-Glu-Tyr True-False 1. T 2. F 3. F 4. T 5. T 6. F 7. F 8. T 9. T 10. F
Chapter 20 Nucleic Acids
247
Multiple Choice 1. Which structures are named correctly? (Sec. 20.2)
a) I, II b) II, III c) III, IV d) I, III
2. Which structure is a nucleoside? (Sec. 20.2)
HN
N
H
O
O
N
N N
N
NH2
H
HN
N N
N
NH2
O
H
HN
N
H
O
O
CH3
guanineI
thymineII
adenineIII
uracilIV
d)c)
b)a)
OHOH2C
O
PO
O
O
OH
OHON
HN
HOH2C
OH
O
CH3
O
OH
ON
HN
HOH2C
O
CH3
ON
N N
N
NH2
HO
PO
O
O
Chapter 20 Nucleic Acids
248
3. Which structures are named correctly? (Sec. 20.2)
a) I, II b) II, III c) I, IV d) II, IV
cytidine 3'-diphosphateII
thymidine 5'-monophosphateI
ON
N
HOH2C
O
PO
O
O
NH2
CH3
O
P OO
O
OH
ON
HN
HOH2C
O
PO
O
O
O
CH3
O
OH
adenosine 5'-diphosphateIV
adenosine 5'-monophosphateIII
ON
N
OH2C
OH
NH2
N
N
HP
O
O
O
OH
P
O
O
OO
N
HN
OH2C
OH
O
N
N
H2NH
P
O
O
O
OH
Chapter 20 Nucleic Acids
249
4. Which nucleotides are named correctly? (Sec. 20.2)
a) I, III b) II, III c) III, IV d) II, IV
ON
HN
OH2C
OH
O
CH3
O
OH
P
O
O
O
ON
HN
OH2C
OH
O
N
N
H2NH
P
O
O
O
OH
5'-TMPI
3'-GMPII
ON
HN
HOH2C
O
PO
O
O
O
CH3
O
P OO
O
OH
3'-TDPIII
ON
N
OH2C
OH
NH2
N
N
HP
O
O
O
OH
P
O
O
O
5'-GDPIV
Chapter 20 Nucleic Acids
250
5. What is the correct name for this structure? (Sec. 20.2)
a) 5’-dAMP b) 5’-TMP c) 3’-AMP d) 3’-dTMP
6. How do DNA and RNA differ? (Sec. 20.3, 20.4)
I) the position of attachment of phosphate groups II) the position of attachment of base groups III) the sugar structure at C-2’ IV) structure of bases
a) I, II b) II, III c) III, IV d) II, IV
7. Which are the correct pairings of bases in the structure of DNA? (Sec. 20.3)
I) A-C II) G-T III) A-G IV) G-C V) A-T VI) C-T
a) I, II b) III, V c) III, IV d) IV, V
ON
HN
HOH2C
O
O
CH3
O
P O
O
O
Chapter 20 Nucleic Acids
251
8. In both RNA and DNA structures, the phosphate groups are attached to the sugar structure at which positions? (Sec. 20.3, 20.4)
a) 5’, 5’ b) 3’, 3’ c) 3’, 5’ d) 5’, 3’
9. What is the charge on adenosine phosphate at blood serum pH of 7.4? (Sec. 20.3)
a) 0 b) –1 c) –2 d) –3
10. Which is the complementary tetranucleotide for 5’-AGCT-3’? (Sec. 20.3)
a) 5’-TCGA-3’ b) 5’-CTAG-3’ c) 5’-AGCT-3’ d) 5’-GATC-3’
11. How many nucleotides direct a specific amino acid into a polypeptide sequence? (Sec. 20.5)
a) 1 b) 2 c) 3 d) 4
12. Which is the DNA complement for 5’-ACCGTTAAT-3’? (Sec. 20.3)
a) 5’-ATTAACGGT-3’ b) 5’-GTTACCGGC-3’ c) 5’-TGGCAATTA-3’ d) 5’-CAATGGCCG-3’
Chapter 20 Nucleic Acids
252
13. Hydrogen bonding is strongest between which two bases? (Sec. 20.3)
a) I, II b) I, IV c) II, III d) II, IV
14. Where does protein synthesis occur? (Sec. 20.4)
a) chromatin b) ribosome c) codon d) histones
15. Which is the complementary sequence in RNA for the DNA sequence 5’-AATCAGTT-3’? (Sec. 20.4)
a) 5’-AAUCAGUU-3’ b) 5’-AACUGAUU-3’ c) 5’-UUAGUCAA-3’ d) 5’-CCAUCGAA-3’
16. A complete turn of the DNA helix occurs at which distance? (Sec. 20.3)
a) 34 Å b) 10 Å c) 20 Å d) 4 Å
17. Which statement about the base mole-percent composition of DNA is true? (Sec. 20.3)
a) A=G=C=T b) (A+G)=(C+T) c) (A+T)=(G+C) d) There is no relationship
18. The backbone of DNA is best described as: (Sec. 20.3)
a) pairs of complementary bases b) poly(1,3-diol-phosphate esters) c) pyrophosphates d) sugar glycosides
HN
N
H
O
O
CH3HN
N N
N
NH2
O
H
N
N N
N
NH2
H
N
N
H
NH2
O
I II III IV
Chapter 20 Nucleic Acids
253
19. Which statements about differences between DNA and RNA are true? (Sec. 20.3, 20.4)
I) The sugar unit is E-D-ribose in RNA and E-2-deoxyribose in DNA. II) The pyrimidine bases are uracil and thymine in RNA and cytosine and thymine in DNA. III) RNA is single stranded, DNA double stranded. IV) The phosphodiester groups join the 3’ to 5’ ends of sugars in RNA, and join the 5’ to 3’ ends in DNA.
a) I, II b) I, III c) II, III d) III, IV
20. Which are types of RNA? (Sec. 20.4)
I) ribosomal II) histonal III) helix IV) transfer
a) I, II b) I, III c) II, IV d) I, IV
21. Which is the order of increasing percentage in cells of messenger RNA, transfer RNA, ribosomal RNA (least first)? (Sec. 20.4)
a) mRNA, tRNA, rRNA b) tRNA, rRNA, mRNA c) rRNA, tRNA, mRNA d) mRNA, rRNA, tRNA
22. Which statements about mRNA codons are correct? (Sec. 20.4)
I) Each amino acid is coded by only one codon. II) Codons code for several amino acids. III) UAA, UAG, UGA are stop codons. IV) Several amino acids are coded by more than one codon.
a) I, II b) III, IV c) I, III d) II, IV
23. Which is the key to the chain termination method of DNA sequencing? (Sec. 20.6)
a) polyacrylamide gels b) restriction endonucleases c) primer d) 2’,3’-dideoxynucleoside triphosphate
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24. Which is the key to in vitro DNA replication? (Sec. 20.6)
a) polyacrylamide gels b) restriction endonucleases c) primer d) 2’,3’-dideoxynucleoside triphosphate
25. Which statements about restriction endonucleases are true? (Sec. 20.6)
I) Each cleave DNA at the same site, but leave different fragment lengths. II) Each recognizes 4 to 8 nucleotides, and cleaves at all sites containing the sequence. III) Approximately 1000 restriction endonucleases have been isolated and characterized. IV) Each cleaves the DNA strand by reducing the base off at the sugar 1’ position.
a) I, IV b) II, IV c) II, III d) III, IV
Fill in the Blank 1. The name of the following base is ____________________________. (Sec. 20.2)
NH
NH
O
O
2. The name of the following nucleoside is _____________________________________. (Sec. 20.2)
N
NNH
NNH2
O
O
OHOH
CH2OH
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3. The name of the following nucleotide is _____________________________________. (Sec. 20.2)
N
NO
NH2
O
OHOH
CH2OP
O
O
O
4. The complementary DNA single strand of 5’-AGTGTTCCAGT-3’ is 5’-____________________________-3’. (Sec. 20.3) 5. The complementary RNA strand to the DNA single strand 5’-GGACTTGACTA-3’ is 5’-____________________________-3’. (Sec. 20.4) 6. The first four amino acids of the protein coded for by AUUAUCCAUAAUGGUGGAAAACGA are __________________________________________________________. (Sec. 20.5) 7. The first four amino acids of the protein coded for by GCUGCCGAUGACGGACGGUGGUGU are __________________________________________________________. (Sec. 20.5) 8. An mRNA strand that codes for the pentapeptide Ile-Thr-Pro-Lys-Arg could have __________ codons in the first position. (Sec. 20.5) 9. An mRNA strand that codes for the pentapeptide Met-Ser-Tyr-Met-Cys could have __________ codons in the first position. (Sec. 20.5) 10. The original DNA strand that results in the following fragments after the Dideoxy method is 5’-_____________________________-3’. (Sec. 20.6) Primer = AGCT Fragments AAGCT, GAAGCT, AGAAGCT, AAGAAGCT, CAAGAAGCT, TCAAGAAGCT True-False 1. The following nucleoside is named Cytidine. (Sec. 20.2)
N
NO
NH2
O
OHOH
CH2OP
O
O
O
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2. The following nucleotide is named 5’-Guanisine diphosphate. (Sec. 20.2)
N
NNH
NNH2
O
O
OHOH
CH2
OPO
O
O
PO
O
O
3. The mole % of purine bases must be equal in human DNA. (Sec. 20.3) 4. The tertiary structure of DNA involves supercoiling. (Sec. 20.3) 5. t-RNA is the lowest molecular weight and most abundant of the RNAs. (Sec. 20.4) 6. mRNA is the shortest lived of the RNAs and the least abundant. (Sec. 20.4) 7. The complementary strand of mRNA to the DNA sequence TAGAAGTAG is ATCTTCATC. (Sec. 20.4) 8. tRNA with the codon UGA codes for Cys. (Sec. 20.5) 9. If the smallest fragment produced during the Dideoxy method and separated by PAGE includes the primer and the base T, the original DNA template begins with T after the primer sequence. (Sec. 20.6) 10. The Chain Termination method uses dideoxy nucleosides to stop DNA synthesis. (Sec. 20.6)
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Answers Multiple Choice 1. b 2. c 3. d 4. a 5. d 6. c 7. d 8. c 9. c 10. c 11. c 12. a 13. b 14. b 15. b 16. a 17. b 18. b 19. b 20. d 21. a 22. b 23. d 24. c 25. c Fill in the Blank 1. Thymine 2. Guanisine 3. 5’-cytidine monophosphate 4. 5’-ACTGGAACACT-3’ 5. 5’-UAGUCAAGUCC-3’ 6. Ile-Ile-His-Asn 7. Ala-Ala-Asp-Asp 8. 3 9. 1 10. 5’-AGTTCT-3’ True-False 1. F 2. T 3. F 4. T 5. F 6. T 7. F 8. F 9. F 10. T
Chapter 21 Lipids
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Multiple Choice 1. Which saturated fatty acids have the correct name? (Sec. 21.2)
I) CH3(CH2)10COOH – stearic acid II) CH3(CH2)14COOH – palmitic acid III) CH3(CH2)16COOH – lauric acid IV) CH3(CH2)18COOH – arachidic acid
a) I, II b) III, IV c) I, III d) II, IV
2. Which properties are characteristic of the most abundant fatty acids found in plants and animals? (Sec. 21.2)
I) They contain an even number of carbon atoms, in the range 10-20. II) The cis isomer predominates. III) The unsaturated fatty acids have higher melting points than the corresponding saturated acids. IV) The most abundant fatty acids are lauric, myristic and linolenic.
a) I, II b) III, IV c) I, III d) II, IV
3. Which physical property of triacylglycerols rich in saturated fatty acids is responsible for the higher melting point than the corresponding unsaturated compounds? (Sec. 21.2)
a) Dispersion forces b) Hydrophilic interactions c) Cis-carbon-carbon double bond steric interactions d) Hydrogen bonding
4. Which physical property of triacylglycerols rich in unsaturated fatty acids is responsible for the lower melting point than the corresponding saturated compounds? (Sec. 21.2)
a) Van der Waals attractions b) Hydrophilic interactions c) Cis-carbon-carbon double bond steric interactions d) Hydrogen bonding
5. Deposits and films are a problem with soaps but not detergents because of which property? (Sec. 21.3)
a) Soaps form soluble calcium salts. b) Detergents form more stable micelles. c) Detergents do not form insoluble calcium salts. d) Soap micelles are unstable in acid.
6. How many triglycerides, including stereoisomers, are possible if two fatty acids are present in the triglyceride? (Sec. 21.2)
a) 3 b) 4 c) 5 d) 6
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7. Which natural products have structures derived from cholesterol? (Sec. 21.5, 21.7)
I) vitamin A II) vitamin D III) cholic acid IV) cortisone V) squalene
a) I, II, III b) II, III, IV c) III, IV, V d) I, III, V
8. Which is not a characteristic group in phospholipids? (Sec. 21.4)
a) phosphate esters b) fatty acid esters c) glycerides d) polyamides
9. Which property of phospholipids accounts for their ability to form micelles? (Sec. 21.4)
a) nonpolarity b) unsaturation c) hydrophilicity and lipophilicity d) lipophilicity
10. Which property of phospholipids accounts for their ability to form fluid membranes? (Sec. 21.4)
a) nonpolarity b) unsaturation c) hydrophilicity and lipophilicity d) lipophilicity
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11. Which is the structure of a phosphatidyl choline? (Sec. 21.4)
CH2
CH
CH2
O
O
(CH2)16CH3
O
O
(CH2)14CH3
OP
O
O
O(CH3)3NCH2CH2
CH2
CH
CH2
O
O
(CH2)16CH3
O
O(CH2)14CH3
OP
O
O
OH2NCH2CH2CH2
CH
CH2
O
O
(CH2)16CH3
O
O(CH2)14CH3
OP
O
O
OCH2CH
COO
NH3
CH2
CH
CH2
O
O
(CH2)16CH3
O
O
(CH2)14CH3
OP
O
O
OOHOH
OHOH
OH
a)
b)
c)
d)
+
+-
12. The fluid-mosaic model of the lipid bilayer states; (Sec. 21.4)
a) lipids coexist side by side as discreet units and proteins float in the bilayer, able to move along the plane of the membrane. b) the lipids form new covalent bonds between chains and lock the proteins into position, much like a mosaic tile.
c) the lipids form a fluid-like membrane that metabolic components (the mosaic) can freely cross. d) the lipid bilayer forms a rigid structure with channels that allow fluid to pass. 13. Which are the most common fatty acids found in phospholipids? (Sec. 21.4) a) palmioleic, stearic, lauric b) lauric, myristic, palmitic c) palmitic, stearic, oleic d) stearic arachidic, oleic
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14. Which is the number of stereocenters in methandrostenolone? (Sec. 21.5)
O
CH3
CH3OH
H H
CH3
a) 4 b) 6 c) 8 d) 10 15. Which reagents could be used to harden an oil to a fat? (Sec. 21.3)
a) NaBH4 / H2O b) Ni / H2 c) Ag(NH3)2
+ / H2O d) Cu2+ / buffer
16. Which common structural feature of vitamin E and vitamin K1 best accounts for the greater solubility of these molecules in organic solvent than water? (Sec. 21.7)
a) aromatic rings b) oxygen atoms c) 4 isoprene units d) a quinone / hydroquinone units
O
O
CH3
O CH3CH3
H3C
HO
CH3 vitamin K1
vitamin E
Chapter 21 Lipids
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17. Which is a prostaglandin? (Sec. 21.6)
18. Which structure is vitamin A? (Sec. 21.7)
CH3
CH3
CH3
CH3 CH3
CH2OHCOOH
HO HHO
HO
O
H H
OHCCH2OHCH3
H
HO
CH3
O
HO
a) b)
c) d)
CH3
CH3
CH3
CH3 CH3
CH2OHCOOH
HO HHO
HO
O
H H
OHCCH2OHCH3
H
HO
CH3
O
HO
a) b)
c) d)
Chapter 21 Lipids
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19. Which structure is a cortisone? (Sec. 21.5)
20. Fats, oils, phospholipids, prostaglandins and steroids have which properties in common? (Sec. 21.1)
I) oxygen functionality II) nonpolar groups III) rings IV) unsaturation
a) I, II b) III, IV c) I, III d) II, IV
CH3
CH3
CH3
CH3 CH3
CH2OHCOOH
HO HHO
HO
O
H H
OHCCH2OHCH3
H
HO
CH3
O
HO
a) b)
c) d)
Chapter 21 Lipids
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21. Which is the best description of the first step (A) of the biosynthesis of prostaglandin? (Sec. 21.6)
a) hydration b) reduction c) oxidation d) Claisen condensation
22. Which is the best description of the second step (B) of the biosynthesis of prostaglandins? (Sec. 21.6)
a) hydration b) reduction c) oxidation d) Claisen condensation
COOH
COOHO
O
OOH
A
COOHO
O
OOH
COOHO
O
OH
B
Chapter 21 Lipids
265
23. Which statements about steroids are false? (Sec. 21.5)
I) The fusion of all rings is cis. II) Sex hormones, adrenocorticoid hormones, bile acids and vitamin D are derived from cholesterol. III) The biosynthesis of cholesterol produces several isomers. IV) Steroids are tetracyclic ring systems
a) I, III b) II, IV c) I, II d) III, IV
24. Which statements about vitamins are true? (Sec. 21.7)
I) Vitamins A, D, E and K are fat soluble. II) Vitamins A, D, E and K are derived from cholesterol. III) Vitamins A, D, E and K each contain 4 isoprene units. IV) Vitamins A, D, E and K have distinct physiological activities.
a) II, III b) III, IV c) I, III d) I, IV
25. The key step in the preparation of soap, saponification, is best described by which mechanism? (Sec. 21.3)
a) base catalyzed acyl addition b) electrophilic addition c) acid catalyzed acyl substitution d) base catalyzed acyl substitution
Fill in the Blank 1. The melting point order of the following fatty acids is (lowest to highest), lauric (12:0) palmitic (16:0) palmitoleic (16:1) oleic (18:1) _______ _______ _______ ______ (Sec. 21.2) 2. The lower melting point of unsaturated fatty acids compared to saturated fatty acids is due to ______________________________ differences. (Sec. 21.2)
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266
3. Complete the reaction below by providing the missing products. (Sec. 21.3)
CH2
CH
CH2
O
O
O
O
(CH2)14CH3O
(CH2)7 CH
CH
(CH2)7CH3
O
(CH2)16CH3
CH2
CH
CH2
OH
OH
OH
3NaOH, H2O+
4. Complete the structure of the alkylbenzene sulfonate detergent below. (Sec. 21.3)
CH3(CH2)12CH2
5. Complete the structure of the phospholipid below. (Sec. 21.4)
CH2
CH
CH2
O
O
(CH2)16CH3
O
O
(CH2)14CH3
OP
O
O 6. The forces which drive bilayer formation by phospholipids are __________________ and ________________. (Sec. 21.4) 7. Androsterone has ________ stereocenters and ____________ possible stereoisomers. (Sec. 21.5)
OH
CH3 H
CH3O
H H
8. Vitamin A precursor E-carotene belongs to the _____________ class of compounds and contains ________ isoprene units. (Sec. 21.7) 9. Prostaglandin is a member of the _________________ class of compounds, which are synthesized from ____________________. (Sec. 21.6) 10. Vitamins A, D, E, and K are included in the lipid class because they are _______ soluble. (Sec. 21.7)
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267
True-False 1. Stearic acid is an unsaturated fatty acid. (Sec. 21.2) 2. Human fat has more unsaturated fatty acids than plant fats. (Sec. 21.2) 3. Soaps and detergents form micelles when added to water. (Sec. 21.3) 4. Soap micelles form in water by aggregating the negatively charged carboxylate groups toward the inside and the lipophilic carbon chains toward the outside of the micelle. (Sec. 21.3) 5. The forces that drive micelle and lipid bilayer formation are the same. (Sec. 21.4) 6. There are several stereoisomers of cholesterol found in living systems. (Sec. 21.5) 7. Aldosterone is an androgen. (Sec. 21.5) 8. Vitamin D precursors have the cholesterol ring system. (Sec. 21.7) 9. Vitamin E is required for blood clotting. (Sec. 21.7) 10. Prostaglandins are involved with the inflammatory response. (Sec. 21.6)
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Answers Multiple Choice 1. d 2. a 3. a 4. c 5. c 6. d 7. b 8. d 9. c 10. c 11. b 12. a 13. c 14. b 15. b 16. c 17. b 18. a 19. c 20. a 21. c 22. b 23. a 24. d 25. d Fill in the Blank 1. 3, 4, 1, 2 2. Conformational 3.
-O
O
(CH2)16CH3
-OO
(CH2)14CH3
-OO
(CH2)7 CH
CH
(CH2)7CH3
4.
CH3(CH2)12CH2 SO3
_
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5.
CH2
CH
CH2
O
O(CH2)16CH3
O
O(CH2)14CH3
OP
O
O
H2NCH2CH2O
CH2
CH
CH2
O
O
(CH2)16CH3
O
O(CH2)14CH3
OP
O
O
(CH3)3NCH2CH2O
CH2
CH
CH2
O
O
(CH2)16CH3
O
O(CH2)14CH3
OP
O
O
OCH2
CHNH3
OOC
CH2
CH
CH2
O
O(CH2)16CH3
O
O(CH2)14CH3
OP
O
O
OOH
OH
OHOH OH
_
+
or
or
or
6. hydrophobic and electrostatic 7. 7, 128 8. terpene, 8 9. eicosanoid, arachidonic acid 10. fat or low polarity organic True-False 1. F 2. F 3. T 4. F
Chapter 21 Lipids
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5. T 6. F 7. F 8. T 9. F 10. T
Chapter 22 The Organic Chemistry of Metabolism
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Multiple Choice 1. Which are oxidation / reduction reagents in the metabolism of fatty acids? (Sec. 22.2, 22.6)
I) ATP II) ADP III) NAD+ / NADH IV) FAD / FADH2
a) I, II b) III, IV c) I, III d) II, IV
2. Which are agents for energy storage and transport? (Sec. 22.2)
I) ATP II) ADP III) NAD+ / NADH IV) FAD / FADH2
a) I, II b) III, IV c) I, III d) II, IV
3. Which is the oxidizing agent for the following reaction? (Sec. 22.6)
a) FAD b) FADH2 c) NAD+ d) NADH
CH2CH2CH2CSCoA
O
C CH3C
H CSCoA
H
O
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4. Which is the oxidizing agent for the following reaction? (Sec. 22.6)
a) FAD b) FADH2 c) NAD+ d) NADH
5. Which is reagent X and product Y in this reaction? (Sec. 22.6)
a) X= acetyl CoA, Y= coenzyme A b) X=coenzyme A, Y= acetyl CoA c) X= FAD, Y= FADH2 d) X= NAD+, Y= NADH
6. The following are key steps in fatty acid metabolism. What is the best description for the first step (A)? (Sec. 22.6)
a) oxidation b) hydration c) reverse-Claisen condensation d) selective reduction
CH3CHCH2CSCoA
OH O
CH3CCH2CSCoA
O O
CH3CH2CCH2CSCoA
O O
CH3CH2CSCoA
OX
+ Y
RCH CHCSCoA
O
RCH CH2CSCoA
OOH
RC CH2CSCoA
OO
RCSCoA
O
CH3CSCoA
O+
A B
C
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7. The following are key steps in fatty acid metabolism. What is the best description for the first step (B)? (Sec. 22.6)
a) oxidation b) hydration c) reverse-Claisen condensation d) selective reduction
8. The following are key steps in fatty acid metabolism. What is the best description for the first step (C)? (Sec. 22.6)
a) oxidation b) hydration c) reverse-Claisen condensation d) selective reduction
9. The biosynthesis of butanoic acid proceeds via a Claisen reaction of Acetyl-CoA. If the starting material is labeled at the methyl carbon atom, which atoms will be labeled in the product? (Sec. 22.6)
a) I, II b) I, III c) II, III d) II, IV
RCH CHCSCoA
O
RCH CH2CSCoA
OOH
RC CH2CSCoA
OO
RCSCoA
O
CH3CSCoA
O+
A B
C
RCH CHCSCoA
O
RCH CH2CSCoA
OOH
RC CH2CSCoA
OO
RCSCoA
O
CH3CSCoA
O+
A B
C
CH3CSCoA
O
CH3CH2CH2COH
O
I II III IV
Chapter 22 The Organic Chemistry of Metabolism
274
10. Which best describes this reaction? (Sec. 22.6)
a) reverse aldol reaction b) aldol reaction c) reverse-Claisen condensation d) Claisen condensation
11. Unsaturated fatty acids require an additional enzyme in the metabolic pathway. Which process involves this enzyme? (Sec. 22.6)
a) oxidation b) reduction c) enol / keto isomerization d) cis / trans isomerization
12. Which agent initially activates fatty acids for further reaction? (Sec. 22.6)
a) NAD+ b) FAD c) Coenzyme A + ATP d) ADP
13. Which statements describing E-oxidation of fatty acid are true? (Sec. 22.6)
I) More energy is released in the oxidation of fatty acids than sugars. II) Only NAD+ / NADH are involved in the reactions. III) The series of four reactions is repeated until the entire fatty acid chain is degraded to acetyl- CoA. IV) The activated fatty acid is a carboxylic-diphosphoric mixed anhydride.
a) II, IV b) I, III c) II, III d) I, IV
14. Which statement is true concerning the balanced half reaction for the oxidation of glucose to pyruvate? (Sec. 22.3, 22.4)
a) The reaction produces two moles of oxygen. b) The reaction is a four-electron oxidation. c) The reaction uses two moles of NAD+. d) The reaction uses two moles of FAD
CH3CH2CCH2CSCoA
O O
CH3CH2CSCoA
OX
+ Y
Chapter 22 The Organic Chemistry of Metabolism
275
15. Which reactions are involved in the conversion of pyruvate to ethanol? (Sec. 22.5)
I) oxidation II) reduction III) decarboxylation IV) keto-enol tautomerization
a) I, III b) II, IV c) II, III d) III, IV
16. If carbon atom 3 of glucose is labeled with 13C, which carbon atom is labeled after oxidation to pyruvate? (Sec. 22.5)
a) carbon atom 1 b) carbon atom 2 c) carbon atom 3 d) carbon atoms 1 and 2
17. Which describes Step 4 of glycolysis, the cleavage of fructose 1,6-bisphosphate to two trioses? (Sec. 22.4)
a) Claisen condensation b) aldol addition reaction c) reverse-Claisen condensation d) reverse-Aldol reaction
18. How many moles of ethanol and CO2 are produced in the glycolysis and fermentation of sucrose? (Sec. 22.5)
a) 2 moles ethanol, 2 moles CO2 b) 2 moles ethanol, 4 moles CO2 c) 4 moles ethanol, 4 moles CO2 d) 4 moles ethanol, 4 moles CO2
19. If carbon 2 of glucose is labeled with 13C, which carbon is labeled in the alcohol fermentation products? (Sec. 22.5)
a) CO2 b) ethanol carbon 1 c) ethanol carbon 2 d) ethanol carbon 1 and carbon 2
20. Which describes the effect of lactate fermentation of glucose on blood pH and CO2 concentration? (Sec. 22.5)
a) pH increases, CO2 concentration increases b) pH decreases, CO2 concentration is unchanged c) pH is unchanged, CO2 concentration decreases d) pH decreases, CO2 concentration decreases
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21. If deuterium is substituted for hydrogen in NADH, where will the deuterium be in the final product of the metabolic reduction of pyruvate to lactate? (Sec. 22.5)
a) I b) II c) III d) II, III
22. If palmitic acid is labeled at carbon 2 with 13C, which carbon will be labeled in acetyl-CoA after E-oxidation? (Sec. 22.6)
a) the methyl carbon b) the carbonyl carbon c) both carbons d) neither carbon
23. Which reagents are necessary in the glycolysis of glucose to pyruvate? (Sec. 22.4)
I) NAD+ II) ADP III) HPO4
2- IV) FAD V) ATP
a) I, II, III, V b) II, III, IV, V c) I, III, V d) III, IV, V
24. How many steps are there in the glycolysis pathway? (Sec. 22.4)
a) 4 b) 6 c) 8 d) 10
25. How many steps are there in the fatty acid E-oxidation pathway? (Sec. 22.6)
a) 4 b) 6 c) 8 d) 10
C
H
OH
CO
O
H3C
I II
III
Chapter 22 The Organic Chemistry of Metabolism
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26. Which is the key intermediate in the enzyme catalyzed reverse-aldol reaction of fructose 1,6-bisphosphate to two trioses? (Sec. 22.6)
a) an amine b) an aldehyde c) an imine d) an amide
27. Which statements about carbohydrate digestion and absorption are true? (Sec. 22.3, 22.4)
I) The main function of carbohydrates is as a carbon source. II) Hydrolysis begins in the mouth with D-amylase in saliva. III) Starch is hydrolyzed directly to glucose. IV) Hydrolysis is completed in the small intestine.
a) I, III b) II, IV c) I, IV d) II, III
Fill in the Blank 1. Complete the structure of Nicotinamide adenine dinucleotide (NAD). (Sec. 22.2)
N
N N
N
NH2
O
OHOH
CH2OPO
O
O
PO
O
O CH2O
OHOH
Chapter 22 The Organic Chemistry of Metabolism
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2. Complete the following reaction mechanism by providing the correct mechanism arrows. (Sec. 22.2)
C
OH
H
N+
H
Ad
O
NH2
C
O
N
H
Ad
O
NH2
H
-:Base-Enzyme H-Base-Enzyme
3. Provide the product of the following reaction. (Sec. 22.2)
H
HH
R
HHOOC
+ FAD + FADH2
4. Provide the product of the following reaction. (Sec. 22.4)
O
OHOHOH
OHHOCH2
+ ATPhexokinase
Mg2++ ADP
5. Provide the products of the following reaction. (Sec. 22.4)
CH2OPO3
O
HOH
H OH
H OHCH2OPO3
aldolase+
2-
2-
Chapter 22 The Organic Chemistry of Metabolism
279
6. Provide the product of the following reaction. (Sec. 22.4)
CH2OPO3
O
HOH
H OH
H OHCH2OPO3
2-
2-
H3N-Enzyme-Base:+ -
7. Provide the product of the following reaction. (Sec. 22.5)
CH3 C
O
COO-
+ NADH + H3O+lactate
dehydrogenase + NAD+ + H3O+
8. Provide the product of the following reaction. (Sec. 22.6)
R C
O
CH2 C
O
SCoA R C
OS-Enzyme+ thiolase-S- +
9. Provide the product of the following reaction. (Sec. 22.6)
OOC CH2 C
O
COO CH3 C
O
SCoA+ + H2Ocitrate
synthase + CoA-SH- -
10. Provide the product of the following reaction. (Sec. 22.7)
CH2 COO
CH COO
CO
COO
---
+ H+ + CO2
Chapter 22 The Organic Chemistry of Metabolism
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True-False 1. The citric acid cycle is the main metabolic pathway under anaerobic conditions. (Sec. 22.7) 2. The following structure is ADP. (Sec. 22.2)
N
NNH
NNH2
O
O
OHOH
CH2
OPO
O
O
PO
O
O
3. The following reaction is a reduction of the alcohol, oxidation of NAD=. (Sec. 22.2)
C
H
OH
C
O+ NAD+ + NADH + H+
4. The following structure is FAD. (Sec. 22.2)
N
NH
N
N
N
NN
NNH2
NH2
O
OHOH
CH2OPO
O
O
PO
O
O
CH2
H OH
H OH
H OH
H H
O
O
Chapter 22 The Organic Chemistry of Metabolism
281
5. FAD is reduced in the following reaction. (Sec. 22.2)
CH2 CH2 CH CH+ FAD + FADH2 6. Acetyl-CoA is derived from the degradation of foodstuffs. (Sec. 22.6) 7. The cleavage of fructose-1,6-bisphosphate to two triose phosphates (reaction 4 of the glycolysis sequence) is an example of an aldol reaction. (Sec. 22.6) 8. Pyruvate is the conjugate base of a E-keto carboxylic acid. (Sec. 22.5)
CH3 CO
COO-
9. Cleavage of the E-ketoacyl-CoA in reaction 4 of the�E-oxidation of fatty acids is an example of a retro-Claisen condensation. (Sec. 22.6) 10. The citric acid cycle oxidizes acetyl-CoA to CO2, producing NADH and FADH2. (Sec. 22.7)
Chapter 22 The Organic Chemistry of Metabolism
282
Answers Multiple Choice 1. b 2. a 3. a 4. c 5. b 6. b 7. a 8. c 9. b 10. c 11. d 12. c 13. b 14. b 15. c 16. a 17. d 18. d 19. c 20. b 21. c 22. a 23. a 24. d 25. a 26. c 27. b Fill in the Blank 1.
N
N
N N
N
NH2
O
OHOH
CH2OPO
O
O
PO
O
O CH2O
OHOH
O
NH2
Chapter 22 The Organic Chemistry of Metabolism
283
2.
C
OH
H
N+
H
Ad
O
NH2
C
O
N
H
Ad
O
NH2
H
-:Base-Enzyme H-Base-Enzyme
3.
R
H
H
HOOC 4.
O
OHOHOH
OHO3POH2C
2-
5.
CH2OPO3
O
CH2OH
H O
H OHCH2OPO3
2-
2-+
6.
CH2OPO3
N-Enzyme-Base:
HOH
H OH
H OHCH2OPO3
2-
2-
-
Chapter 22 The Organic Chemistry of Metabolism
284
7.
CH3 COH
HCOO
-
8.
CH3 CO
SCoA
9.
CH2 COO
COH COO
CH2 COO
---
10.
CH2 COO
CH2
CO
COO
-
-
True-False 1. F 2. F 3. F 4. T 5. T 6. T 7. F 8. F 9. T 10. T
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