88657832 organic chemistry brown 3e test bank copy

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.

To order books or for customer service call 1-800-CALL-WILEY (225-5945). Copyright � 2005 by John Wiley & Sons, Inc. Excerpts from this work may be reproduced by instructors for distribution on a not-for-profit basis for testing or instructional purposes only to students enrolled in courses for which the textbook has been adopted. Any other reproduction or translation of this work beyond that permitted by Sections 107 or 108 of the 1976 United States Copyright Act without the permission of the copyright owner is unlawful. Requests for permission or further information should be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030. ISBN 0-471-68692-1 Printed in the United States of America 1 0 9 8 7 6 5 4 3 2 1 Printed and bound by Malloy Lithographing, Inc.

CONTENTS

CHAPTER 1. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1

CHAPTER 2. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 12

CHAPTER 3. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 24

CHAPTER 4. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 36

CHAPTER 5. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 48

CHAPTER 6. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 61

CHAPTER 7. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 75

CHAPTER 8. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 88

CHAPTER 9. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 100

CHAPTER 10. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 116

CHAPTER 11. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 130

CHAPTER 12. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 138

CHAPTER 13. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 148

CHAPTER 14. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 161

CHAPTER 15. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 176

CHAPTER 16. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 191

CHAPTER 17. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 207

CHAPTER 18. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 221

CHAPTER 19. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 235

CHAPTER 20. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 247

CHAPTER 21. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 258

CHAPTER 22. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 271

Chapter 1 Covalent Bonding and Shapes of Molecules

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


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


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


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


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


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


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


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)


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)


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


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


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.


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


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


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


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)


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+


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


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


+ H2O NH3 + H3O+ + Cl-


21


+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


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


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


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


a) 1,3-dimethylcyclohexene b) 2,4-dimethylcyclohexene c) 3,5-dimethylcyclohexene d) 2,4-dimethyl-1-cyclohexene


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


38


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


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


a) IV, III, II, I b) I, II, III, IV c) III, IV, I, II d) III, I, IV, II


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


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


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


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)


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)


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)


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)


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


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


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


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


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


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)


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


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


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


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

+


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)


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-


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


59

5. Br2

CH2Cl2 6.

H+

H2O 7.

Cl2

CH2Cl2 8.

or

9.

+ 10.

Br +

11.

H Cl C+

HClCl

+


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


3. Which compounds contain stereocenters? (Sec. 6.3)


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)


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


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


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


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)


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


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


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


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


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


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


83

Fill in the Blank

1. The major product of the following reaction is,

Cl H

KSCH3

DMSO (Sec. 7.6)


Br H

KOH

H2O (Sec. 7.6)


H I

NH3

(Sec. 7.6)


INaOCH2CH3

CH3CH2OH (Sec. 7.9)


H Br

H2O

(Sec. 7.6)

6. The reagent needed to complete the following reaction is,

Cl (Sec. 7.9)


84


BrH OHH

(racemic)

(Sec. 7.6)


HBrHH3CO H OCH3

+

(Sec. 7.6)

9. The starting material needed to complete the following reaction is,

IKI

CH3CH2OH (Sec. 7.6)


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 > > >


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)


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


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


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


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


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


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.


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


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


94



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


95


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)


OH

H2CrO4

acetoneH2O (Sec. 8.3)


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


96


OH Cl (Sec. 8.3)


O

(Sec. 8.5) 8. The starting material needed to complete the following reaction is,

H3PO4

heat (Sec. 8.3)


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)


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< <


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


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


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


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


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


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


105



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


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)


107


21. Which is the electrophile in the final reaction step for the following reaction? (Sec. 9.7)


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


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)


109


OH

H3PO4

(Sec. 9.6, 9.8) 2. The major product of the following reaction is,

K2Cr2O7

H2SO4


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)


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)


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)


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

> > >


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


114

3.

Br

O 4.

O OH

+

5.

OOOH

+

6. HNO3, H2SO4 7.

ClAlCl3

SO3, H2SO4

8.

Cl

SO3 , H2SO4


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)


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


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


NH2

CH3

NaNO2

HCl, 0° C

CH3

NH2

CH3

NO2O2N

CH3

N+

N

NH2

CH3

NO2O2N

Cl-

a) b) c) d)


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


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


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


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)


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


133

14. Which compounds will have a particularly weak characteristic IR stretching frequency? (Sec. 11.5)


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


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)


135


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


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


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)


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


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


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)


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


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)


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


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


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


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


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)


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


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


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


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)


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)


151



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


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


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


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)


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


155


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


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


NH2

NH3

H2, Ni (Sec. 13.8)

8. The reagents that complete the following reaction are,

H

O

OH

O

(Sec. 13.10)


157


O

1) LiAlH4, ether

2) H2O


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)


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)


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


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


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)


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


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


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


164


a) II, I, III, IV

b) I, II, III, IV

c) III, I, II, IV

d) IV, I, II, III


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


165


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


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


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


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.


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


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


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


O

OH

1) LiAlH4, ether

2)H2O

(Sec. 14.6)

NH2 COH

O

C

O

CH3

I II III


171


OH

O O

OH

OH O

(Sec. 14.6)


O

OHOH

H+

(Sec. 14.7)


OH

O

Cl

O

(Sec. 14.8)


OH

O Oheat

(Sec. 14.9)


OH

O

O

O

(Sec. 14.7)


172


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)


OH

O

ClOH

O

Cl

ClOH

O

Cl

Cl

Cl

OH

O

> > >

(Sec. 14.5)


173


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)


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

+


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


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


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


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)


180

13. Which compounds will yield benzoic acid when hydrolyzed? (Sec. 15.4)

I) benzyl ethanoate II) benzamide III) phenyl ethanoate IV) methyl benzoate


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


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


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)


183

21. Partial hydrolysis of phenobarbitol gives which compound? (Sec. 15.4)


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)


184


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)


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


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)


186

4. The starting material that completes the following reaction is,

NH

N

O


O

Cl

O

O

(Sec. 15.5) 6. The major product that completes the following reaction is,

O

O MgBr

2) H+, H2O

1)


N

O

N


O

OHNH

O

(Sec. 15.4)


187


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


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-

+


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


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)


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


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


194


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


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


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)


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


197

18. Which compounds will undergo decarboxylation upon heating? (Sec. 16.4)


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


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)


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


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


200



O NaOH, H2O

2


H

O

H

O

+NaOH, H2O


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


201


O

O O NaOH, H2O+


OO

O

O

NaOH, H2O


O

O

O

O

+NaOH, H2O


O O

O O

O O

O O

OH

+NaOH, H2O


O

O+ CH3NH2

(Sec. 16.6)


202


O

O O

O+1) NaOCH2CH3, ethanol

2) NaOH, H2O3) HCl, H2O4) heat


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)


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)


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


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


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


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


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


210

10. 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



211


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


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)


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


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


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)


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


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)


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


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)


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


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)


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


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


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)


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


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


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


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


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


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.


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


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


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)


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)


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)


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


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)


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


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


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


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)


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)


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)


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)


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)


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

+ +

+ +


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

+


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)


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


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


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


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


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


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’


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


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.


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


254

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


255

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


256

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)


257

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

258

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


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.


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

Chapter 21 Lipids

259

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

Chapter 21 Lipids

260

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

Chapter 21 Lipids

261

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

262

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

263

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


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

264

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)

Chapter 21 Lipids

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)

Chapter 21 Lipids

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)

Chapter 21 Lipids

268

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

_

Chapter 21 Lipids

269

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

270

5. T 6. F 7. F 8. T 9. F 10. T

Chapter 22 The Organic Chemistry of Metabolism

271

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


2. Which are agents for energy storage and transport? (Sec. 22.2)

I) ATP II) ADP III) NAD+ / NADH IV) FAD / FADH2


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


272

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


273

7. The following are key steps in fatty acid metabolism. What is the best description for the first step (B)? (Sec. 22.6)


8. The following are key steps in fatty acid metabolism. What is the best description for the first step (C)? (Sec. 22.6)


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


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


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


276

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


277

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


278

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


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-


279


CH2OPO3

O

HOH

H OH

H OHCH2OPO3

2-

2-

H3N-Enzyme-Base:+ -


CH3 C

O

COO-

+ NADH + H3O+lactate

dehydrogenase + NAD+ + H3O+


R C

O

CH2 C

O

SCoA R C

OS-Enzyme+ thiolase-S- +


OOC CH2 C

O

COO CH3 C

O

SCoA+ + H2Ocitrate

synthase + CoA-SH- -


CH2 COO

CH COO

CO

COO

---

+ H+ + CO2


280

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


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)


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


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-

-


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

88657832 organic chemistry brown 3e test bank copy

Documents