b. organic chemistry brown 3e test bank

7/26/2019 B. Organic Chemistry Brown 3e Test Bank

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Test Bank

Jeffrey ElbertUniversity of Northern Iowa

INTRODUCTION TO

ORGANIC CHEMISTRY

Third Edition

William BrownBeloit College

Thomas PoonClaremont McKenna, Pitzer, and Scripps Colleges

John Wiley & Sons, Inc.


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CONTENTS

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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


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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, 3s2d) 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) Sec) Cl

d) Br

5. Which atom is described by the Lewis structureA

? (Sec. 1.2)

a) C

b) Pc) Se

d) I

6. Which atom is described by the Lewis structureA

? (Sec. 1.2)

a) C

b) P

c) Sed) 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, IVc) I, II, IV

d) II, III


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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, IVc) 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, IVc) III, IV

d) I, III

11. Which molecules are polar? (Sec. 1.5)

a) I, IV

b) I, IIIc) 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


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3

12. Which molecules are polar? (Sec. 1.5)

a) III, IV, V

b) I, IVc) 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, IIId) 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, IVc) 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

H3C


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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) bentd) 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, Vc) 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) N2c) NH4Cl

d) HCN

20. What is the formal charge of oxygen in H3O+? (Sec. 1.3)

a) 1b) 0

c) +1

d) +2

21. What is the formal charge of indicated carbon in,

NaC CH

(Sec. 1.3)a) 2

b) 1c) 0

d) +1

d)c)

b)a)

H2C CH CH2 O CH3CH3 CH2 CH2 CH

O

CH3 C

O

CH2 CH3CH3 CH

OH

CH CH2

NH3 CO2 H2O H3O+ O3

I II III IV V


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5

22. The carbon has the correct orbital hybridization in which structures? (Sec. 1.7)

a) II, IV, Vb) II, III, IV

c) I, II, IIId) 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 IIIb) 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, IVd) II, III, ,IV

CH3

CH4

CH3

A. I. sp

B. II. sp2

C. III. sp3

sp sp2 sp

2 sp sp

I II III IV V

O C OHC NH2C CH22C 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


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6

25. Carbon has how many valence electrons? (Sec. 1.2)

a) 2

b) 4

c) 6d) 8

26. Oxygen has how many valence electrons? (Sec. 1.2)

a) 4

b) 5c) 6

d) 7

27. Nitrogen has how many valence electrons? (Sec. 1.2)

a) 4

b) 5

c) 6d) 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, Vd) I, III, IV

alcohol aldehyde ketone amine carboxylic acid I II III IV V

C

O

OHH3CN CH3

CH3

HC

O

CH3H3CCH3 OHC

O

H3C


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7

31. Which of the following compounds contains a tertiary (3) alcohol? (Sec. 1.8)

OH

H3C

H3C

CH3

C C

CH3

H3

C

H3

C

CH2

OH

OH

H3C

H3C

HC

OHH3

C

HC

H3

C

CH

CH3

I II III IV

a) I

b) IIc) III

d) IV


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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 calledthe ______ ______. (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)


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9

5. Carbon reacts by gaining 4 electrons to achieve a noble gas configuration. (Sec. 1.3)

6. An atom that gains electrons is called an anion. (Sec. 1.3)

7. Ionic bonds are characterized by the unequal sharing of electrons. (Sec. 1.3)

8. The following molecule is an example of a secondary amine. (Sec. 1.8)

NH2

H3C

H3C

HC

9.CH

3CH

2CH

2CH

2CH

2OH

is a polar molecule. (Sec. 1.5)

10.CH

3ONa

contains only polar covalent bonds. (Sec. 1.3)


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10

Answers

Multiple Choice

1. b2. c

3. d

4. c5. c

6. a

7. d8. c

9. d

10. c

11. b

12. c13. d

14. d

15. d16. b

17. a18. c

19. a20. c

21. b

22. a

23. c

24. c25. b

26. c

27. b28. c

29. c

30. a31. b

Fill in the Blank

1. paired

2. valence3. 6

4. 7

5. octet rule6. C-F

7. polar covalent

8. ketone, alcohol

9. 1 amine, carboxylic acid

10. reactions11. Functional groups

True-False

1. F2. F

3. F4. T

5. F

6. T


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7. F

8. F

9. T

10. F


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Chapter 2 Acids and Bases

12

Multiple Choice

1. Identify the Brnsted-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

VIIVIIVIV

IVIIIIII

+

+

+

+

H2C2H5ONaNaHC2H5OH

ClCH3OH2HClCH3OH

VIV

IVIII

III

++

CH3OH HCl CH3OH2 Cl+ +

C2H5OH NaHC2H5ONa

H2+ +

CH3CO2CH3NH3H3CCO2HCH3NH2


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13

3. Identify the conjugate acids in the following reactions. (Sec. 2.3)

a) I, IV, VI

b) I, III, VIc) II, IV, V

d) I, III, V

4. Which are acid-base reactions according to Brnsted-Lowry theory? (Sec. 2.3)

a) I, IIIb) I, II, II, IV

c) I, II, III

d) I, III, IV

VIV

IVIII

III

++

CH3OH HCl CH3OH2 Cl+ +

C2H5OH NaHC2H5ONa

H2+ +

CH3CO2CH3NH3CH3CO2HCH3NH2

CH3C

O

OH3CNH3

CH3C

O

OHCH3NH2

AlCl3 ClAlCl4

CH3NH2 HClCH3NH3Cl

CH3Li H2O CH4 LiOH

+

+

+

+ +

+I.

II.

III.

IV.


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14

5. Which are acid-base reactions according to the Brnsted-Lowry theory? (Sec. 2.3)

a) Ib) I, III, IV

c) II, III

d) I, IV

6. Which are acid-base reactions according to Lewis theory but not according to the Brnsted-Lowry theory?(Sec. 2.7)

a) I, IIb) III, IV

c) I, III, IV

d) I, II, III, IV

C

O

CH3H3CCH3 C

O

H3C

CH3

CH3

H3C C

O

OH H2O H3C

C

O

OH

3O

NH3 BF3 NH3BF3

OH3C CH3 BF3 O BF3

H3C

H3C

I.

II.

III.

IV.

+

+

+

+

+

++

+

+

+

+

+

IV.

III.

II.

I.

CH3NH3ClHClCH3NH2

CH3NH2BF3BF3CH3NH2

BrFeBr4FeBr3

Br2

HSO4H2O(CH3)3CH2SO4(CH3)3COH


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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, IIIc) 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


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16

11. Which equilibria lie considerably toward the right? (Sec. 2.5)

a) II, IIIb) 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, IVd) I

C

O

OHH3C

NH3 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

OHH3C

C

O

OH3C


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17

13. List the bonds in order of increasing acidity (least to most). (Sec. 2.6)

a) II, III, IV, Ib) 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, Ic) II, III, IV, I

d) I, II, III, IV

15. Which substances are Lewis bases? (Sec. 2.7)

a) I, II

b) I, IIIc) 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

2O AlCl3H3C

CH

CH3

F

I II III IV

HC CH NH2 HC C NH3+ +

a) b) c) d)

HNO3 H2SO4 H2NO3 HSO4+ +

a) b) c) d)


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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 acidb) Lewis base

c) Brnsted acid

d) Brnsted 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 acidb) Lewis base

c) Brnsted acid

d) Brnsted base

22. Which statements about acid-base equilibria are true? (Sec. 2.4)

I. The pKais the negative log10of the acid equilibrium constant.

II. A stronger acid has a pKawith a smaller value than a weaker acid.III. A stronger base has a conjugate acid which has a pKawith a smaller value than a weaker base.

IV. The Ka = K [HA].

a) I, III

b) I, II

c) I, II, IIId) II, III, IV

CH3CH2OCH2CH3 BF3 (CH3CH2)2O BF3+

NH3 H3O H2O NH4+ +

C

O

OH3C

C

O

OH3C

HCNCN+ +

a) b) c) d)

C

CH3

H3C

CH3

CH3OH C

CH3

H3C

CH3

O CH3

H+


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19

23. Which is the order of decreasing acid strength of the following compounds (greatest first)? (Sec. 2.6)

C

O

OHCH

2

ClC

O

OHCH

2

Br C

O

OHCH

2

FC

O

OHCH

2

H

I II III IV

a) II, I, III, IV

b) III, IV, I, IIc) 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

F

OH

OF

OH

O

F

OH

OF

I II III IV

a) I, III, II, IVb) IV, III, II, I

c) II, I, III, IV

d) IV, III, I, II


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20

25. Which is the proper reaction mechanism for the reaction of borontrifluoride and diethyl ether? (Sec. 2.7)

OCH

2CH

3CH

3CH

2 OCH

2CH

3CH

3CH

2

BF3

OCH

2CH

3CH

3CH

2 OCH

2CH

3CH

3CH

2

BF3

OCH

2CH

3CH

3CH

2 O

CH2CH3CH3CH2

BF3

OCH

2CH

3CH

3CH

2 OCH

2CH

3CH

3CH

2

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)

+ H2

OCH3

COH

O

CH3CO-

O

+


NH3 ++NH4Cl CH3CONa

O


+ H2O NH3 + H3O+

+ Cl-


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21


+CH3COH

O

CH3

CONa

O

+ 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. Brnsted-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


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22

7. Water acts as a base in the following reaction. (Sec. 2.3)

+NH3 H2O NH4OH

8. Ammonia acts as a Brnsted-Lowry base in the following reaction. (Sec. 2.3)

+NH4

Cl NaHCO3 NH3 + H2CO3 + NaCl

9. The strongest acid in the following list is sodium bicarbonate. (Sec. 2.4)

NH4

Cl NaHCO3 H2O CH3CH2OH

10. The weakest acid in the following list is acetic acid. (Sec. 2.6)

CH3COH

O

ClCH2

COH

O

FCH2

COH

O

FCH2CH2COH

O


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23

Answers

Multiple Choice

1. d

2. a3. b

4. d

5. d6. b

7. d

8. a9. d

10. d

11. b

12. a

13. c14. b

15. d

16. a17. c

18. b19. b

20. d21. b

22. b

23. c

24. b

25. b

Fill in the Blank1. stronger

2. weaker

3. H3O+

4. CH3COOH + NaCl5. NH4Cl

6. Na2CO3

7. equilibrium arrow pointed to the left

8. equilibrium arrow pointed to the left9. base, acid, c.acid, c. base

10. acid, base, c. base, c. acid

True-False

1. F

2. T

3. F

4. T5. F

6. F

7. F

8. T9. F

10. T


28/288

Chapter 3 Alkanes and Cycloalkanes

Multiple Choice

1. Which of the following are constitutional isomers of 4-isopropyloctane ? (Sec. 3.3)

a) I IV

b) II, III

c I II

I. 3-ethyl-2,4,5-trimethyloctane

II. isobutylcyclohexane

Ill.

4-ethyl-2,2-dimethylheptane

IV.

4-ethyl-2-methyloctane

d) III, IV

2. Which of the following are constitutional isomers

of

trans-1,2-dimethylcyclopentane ? (Sec. 3.3)

ll

IV

a) I Ill, IV

b II, IV, V

c)

ll,Ill,V

d) III, IV, V

3. Which of the following properties are not identical for constitutional isomers? (Sec. 3.9)

a) I, IV

b) II, III

c) I, II

I. molecular formula

II. molecular

weight

Ill.

order of attachment

of atoms

IV. physical

properties

d) Ill, IV

4. Which of the following molecules are constitutional isomers? (Sec. 3.3)

and

b) CH3CH20CH3 and

0

c)

CH3CH2CH

and

d)

CH3CH20H

and

0

CH3CH2CH

0

CH3CCH3

0

CH

3

CCH3

0

CH3CH

24

v


29/288


5. Which of the following belong in the group

of

constitutional isomers for C

1

H

6

0

2

? Sec. 3.3)

a

II,

b) II, IV, V

c) I II, V

d) I

6. Which pairs of molecules are constitutional isomers? Sec. 3.3)

D

C>-

l l ~

IV

a) I IV

b)

I

II

c)

II,

d) III, IV

7. Which is the IUPAC name for the following compound? Sec. 3.4)

H3C

CH3

/

CH-CH

/

2C CH2

I I

CH3 CH3

a) 2-ethyl-3-methylpentane

b) 3,4-dimethylhcxane

c) 2,3-diethylbutane

d) 3-methyl-4-ethylpentane

25

6


30/288


8. Which

is

the IUPAC name for the following cycloalkane ? (Sec. 3.4)

a 2,4-dimethyl-1-ethylcyclopentane

b) I ,3-dimethyl-5-ethylcyclopentane

c) 1-ethyl-2,4-dimethylcyclopentane

d) 1-ethyl-3,5-dimethylcyclopentane

9.

Which is the IUPAC name for the following compound? (Sec. 3.4)

a) cis-1-ethyl-2-methylcyclohexane

b) trans-1-ethyl-2-methylcyclohexane

c) cis-1-methyl-2-ethylcyclohexane

d trans-1-methyl-2-ethylcyclohexane

10.

Which is the structure for trans-1-ethyl-3-isopropylcyclohexane? (Sec. 3.4 and 3.8)

a

b

c

d

H

11.

How many primary carbons are there in the following molecule? (Sec. 3.4)

a) 1

b) 2

c)

4

d 6

26


31/288


12. How many secondary hydrogens are there in the following molecule? Sec. 3.4)

a

1

b

2

c 4

d

9

13. Which structural formulas represent cis forms

of

1,2-dimethylcyclohexane? Sec. 3.8)

H

H

I.

II.

III.

IV.

a)

I, IV

b) II, III

c)

III

IV

d) I, II

14. Which cycloalkanes show cis-trans isomerization? Sec. 3.8)

I.

II.

III.

IV.

V.

a I, V

b l , l l ,V

c)

ll,III,V

d II,

I l l IV

15. In the most stable conformation of trans- I 4-dimethylcyclohexane, what positions do the methyl groups occupy?

Sec. 3.7)

a axiaL axial

b) equatorial, axial

c) equatoriaL equatorial

d) axial, equatorial

27


32/288


16 Which

of

these diaxial forms has the highest energy? (Sec. 3.7)

a)

b)

c)

d)

17 Which compound has the lowest boiling point? (Sec. 3.9)

H3C,

CH3

0

CHCH

2

CH3

H

3

C-C-CH3

/

I

H

3

C

CH3

a)

b

c)

d)

18 Which compound has the highest boiling point? (Sec. 3.9)

CH

2

CH

3

I

H3C-C-CH3

I

CH

2

CH

3

0

a)

b)

c)

d

19 Which is a conformer

of

pentane ? (Sec. 3.7)

CH3

~

~

~

~

H H

H

CH3H

H3C

H CH3

H H CHzCH3

CHzCH3

a

b)

c) d)

20. Which conformation

of

2-methylbutane

is

the most stable? (Sec. 3.7)

H f i ~ C H

~

CH

3

CH3

C ~ C H

H ~ C H 3

H

CH3

H H

H CH3

CH

3

H

H

a)

b

c) d)

28


33/288


21. Which conformer

of

pentane

is

the least stable? (Sec. 3.7)

J H

3

2

3

9fzCH3

CHzCH3

3

H ~ H

M ~

H ~ H

t l

CH3

a)

b

c)

d

22. Which fiaction of petroleum distills at the highest temperature? (Sec. 3.11)

a

gasoline

b) gases

c) fuel oil

d) kerosene

23. What is the term for the process of forming ethene (an unsaturated hydrocarbon) from ethane (a saturated

hydrocarbon)' (Sec. 3.11)

a) combustion

b) fractional distillation

c) thermal cracking

d) catalytic reformation

24. Which molecule has the most negative heat

of

combustion in kcal/mole? (Sec.

3.1

0)

a) methane

b) ethane

c) propane

d) butane

25. Which are the stoichiometric coefficients that complete the following equation? (Sec. 3.10)

a) x

=

9

Y,,

y

=

6, z

=

7

b) x=18,y=12,z=14

c) x = 1 y = l z = 2

d)

X

= 6 , y = 6,

Z

= 4

9


34/288


Fill in the Blank

1

Complete the following reaction by writing the stoichiometric coefficients. (Sec. 3.1 0)

CH3CH CH CH3

D

2

D

C 2

D

H2

2 Complete the following reaction by writing the stoichiometric coefficients. (Sec. 3 1 0)

CH3CH3

D 2 D

C 2

D

H2

3. Write the name for the following molecule. (Sec. 3.4)

4. Write the name for the following molecule. (Sec. 3.4)

H

5 Complete the structure by drawing in the cis-1,3-dimethyl groups. (Sec. 3.8)

6 Complete the structure by drawing in the trans- ,4-dimethyl groups. (Sec. 3.8)

7

What

is

the configuration of the indicated carbon? (Sec. 3.4)

30


35/288


8

What

is

the configuration

of

the indicated carbon? Sec. 3.4)

9 Draw a constitutional isomer ofpropanone. Sec. 3.3)

10 Complete the Newman projection for the least stable conformation of2-methylbutane. Use the appropriate

Newman projection template. Sec. 3.7)

*

I Complete the Newman projection for the most stable conformation of2-methylbutane. Use the appropriate

Newman projection template. Sec. 3.7)

*

3


36/288


True-False

1.

The following structures represent the same molecule. Sec. 3.3)

cc

nd

~ ~ ~

1

2.

The following structures represent the same molecule. Sec. 3.3)

nd

3. The indicated carbon

is

a secondary 2) carbon. Sec. 3.4)

4.

The molecule shown has

12

primary 1

)

hydrogens. Sec. 3.4)

5.

Propanal

is

a primary

1

) alcohol. Sec. 3.6)

6

Propanal and propanol are constitutional isomers. Sec. 3.3)

7.

Pentane and cyclopentane are consti tutional isomers. Sec. 3.3)

8 Alkanes all have lower densities than water. Sec. 3.9)

9.

The Newman projection below shows 2,3-dimethylbutane in the most stable conformation. Sec. 3.7)

32


37/288


10 The Newman projection below shows n-pentane in a gauche conformation. Sec. 3.7)

33


38/288

Answers

Multiple Choice

I

d

2

d

3. d

4

c

5.

d

6 a

7. b

8. c

9. b

lO a

11. c

12. c

13. a

14 d

15 c

16 c

17 c

18.

a

19 d

20. b

21

a

22 c

23 c

24 d

25 a

Fill in the Blank

I. 6

/:,,

4, 5

2. 3 /:,, 2, 3

3. 3,5-diethylheptane

4. 1-ethyl-2,4-dimethylcyclohexane

5.

6

H

H

r cH

3

H

7

quaternary 4)

8

secondary 2)


CH

MH

H

etc.

etc.

34


39/288

True-False

l T

2 T

3. F

4. T

5 F

6 F

7 r

8 T

9. F

10 F


enol is also a possibility

35


40/288

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, 109d) 109, 120

2. Which is the best description for the indicated bond in the following compound? (Sec. 4.2)

a) sp3-sp3

b) sp3-sp3and 2p-2p

c) sp2-sp2and2p-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


41/288


37

5. Which is the correct name for the following compound? (Sec. 4.3)

a) 2E, 5E-5-methyl-2,5-heptadieneb) 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-dimethylcyclohexenec) 3,5-dimethylcyclohexene

d) 2,4-dimethyl-1-cyclohexene


a) E-2-ethyl-2-buteneb) 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-butynec) 3-butened) 2-butyne

3CC

C

CH2

CC

CH3

CH3

H H

H

CH3

CH3

C C

3C

H

CH3

CH2CH3

C C CH3H3C


42/288


38

9. Which is the IUPAC name for the following compound? (Sec. 4.3)

a) 1,1-dimethyl-4-ethyl-2,5-cyclohexadiene

b) 1-ethyl-4,4-dimethyl-2,5-cyclohexadiene

c) 3-ethyl-6,6-dimethyl-1,4-cyclohexadiene

d) 6-ethyl-3,3-dimethyl-1,4-cyclohexadiene

10. Which of the following alkenes do not show cis-trans isomerization? (Sec. 4.3)

I) 2-methyl-2-hexene

II) 1-chloro-1-butene

III) 1-methylcyclohexeneIV) 2-methyl-3-hexene

a) I, II

b) III, IVc) II, III, IV

d) I, III

11. Which of the following alkenes show cis-trans isomerization? (Sec. 4.3)

I) 1-chloropropene

II) 3-methylcyclohexeneIII) 2,6-dimethyl-2,5-octadiene

IV) 3-ethyl-3-methyl-1-pentene

a) I, IIb) 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) 2b) 3

c) 6

d) 8

13. How many cycloalkanes of molecular formula C5H10show cis-trans isomerism? (Sec. 4.3)

a) 1

b) 2c) 3

d) 4

H3C

3C

CH2CH3


43/288


39

14. How many cycloalkanes of molecular formula C6H12do not show cis-trans isomerization? (Sec. 4.3)

a) 2

b) 3c) 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, IIId) IV, II, III, I


a) IV, III, II, I

b) I, II, III, IVc) 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


44/288


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) 3c) 4

d) 6

21. How many distinct terpene structure types can be made from the assembly of 2-isoprene units? (Sec. 4.5)

a) 1b) 2

c) 3

d) 4

C C

3C

Br

CH2CH3

CH3C C

Br

CH

CH3

CH2CH3H

HC C

H3C

Br

CH3

CH2CH3C 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

H

2C

2CCH

C

CH3H3C


45/288


41

22. How many isoprene units are there in vitamin A? (Sec. 4.5)

a) 2

b) 3c) 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, IIIb) 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

CH

CH3

C CH3C CH3

I II III IV


46/288


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)


47/288


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

3

4

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=CH2is;

> > >

(Sec. 4.3)


48/288


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)

< < > >

5. The following groups are listed in order of increasing priority (lowest first). (Sec. 4.3)O

H OCH

2CH

3

O

Cl Cl< < > >

True-False

1. F

2. F3. F

4. F

5. T6. T

7. F

8. F

9. T

10. F


52/288

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) IIb) 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

C

D

E E

E E

reaction coordinate

Areaction coordinate

B

reaction coordinate reaction coordinate

C D


53/288


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 Markovnikovs 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, IVc) I, IV

d) I, III

8. Arrange these carbocations in order of increasing stability (least to most). (Sec. 5.3)

a) I, II, III, IVb) 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


54/288


50

9. Arrange these carbocations in order of increasing stability (least to most). (Sec. 5.3)

a) I, II, IIIb) 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, IVc) II, IIId) I, IV

11. Which reagents react with an alkene by anti addition? (Sec. 5.3 - 5.5)

I. Cl2 II. Br2 III. H2/Pt IV. OsO4/ROOH

a) I, II

b) III, IVc) II, III

d) I, IV

12. Which reagents react with an alkene in a Markovnikov orientation? (Sec. 5.3)

I. HBr II. H2O/H2SO4 III. Br2 IV. OsO4/ROOH

a) I, II

b) III, IVc) 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-propanolc) 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, IIIb) I, II, IV

c) II, IV

d) III, IV

I II III


55/288


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 C8H14and 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

H

H

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)


56/288


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



A B

C D


57/288


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

C

D


58/288


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


HBr

CH2Cl

2


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


59/288


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+

HCl

Cl

+


60/288


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< > >

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)


61/288


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-


62/288


58

Answers

Multiple Choice

1. d2. c

3. a

4. b5. c

6. c

7. c8. b

9. d

10. b

11. a

12. a13. c

14. a

15. b16. b

17. d18. a

19. a20. b

21. d

22. c

23. a

24. d25. d

Fill in the Blank

1. Br2, OsO4, H2

2.

OH

OH

3.

Br

4.

H H


63/288


59

5.

Br2

CH2Cl

2

6.

H+

H2O

7.

Cl2

CH2Cl

2

8.

or

9.

+

10.

Br+

11.

H Cl C+

HCl

Cl

+


64/288


60

True-False

1. F

2. F

3. T4. F

5. F

6. F7. T

8. F

9. F10. F


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Chapter 6 Chirality

61

Multiple Choice

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

I) 1-chloropentaneII) 2-chloropentane

III) 3-chloropentane

IV) 1,2-dichloropentane

a) I, II

b) III, IVc) I, III

d) II, IV


I) 2-methylpentane

II) chlorocyclohexaneIII) 3-methyl-2-butanol

IV) 2-hydroxypropanoic acid

a) I, IIb) III, IV

c) I, III

d) II, IV


a) I, II

b) III, IVc) I, III

d) II, IV

HO OH CH

OH

CH2

OH

CH3CCH2CH3

O

CHCHCH3

OHH3C

H3C

I. II.

III. IV.


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Chapter 6 Chirality

62

4. Which compounds have multiple stereocenters? (Sec. 6.3, 6.5)

a) I, IIb) III, IV

c) II, IIId) 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) 3d) 4

7. How many stereoisomers are possible for the following structure? (Sec. 6.2-6.3)

a) 1

b) 2c) 3

d) 4

IV.III.

II.I.

CHO

CH2COH

CH2

COH

O

O

COH

O

CH3CHCHCH3

Cl OH

CH3CHCH COH

HO OH O

CH3CHCHCH3

CH3HO

CH3CHCHCOH

O

NH2

OH


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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, IIId) I, II, III

CH3

OHHOC

H

O

Br CH3

Cl

CH2CH3

H

COHH3C

HO

O

Br

Cl

H3CH2C

H3C

I CH3

H

OHI OH

CH3

H

I.

II.

III.

V.IV.

III.II.I.

H2C C

CH2CH2CH2

Cl

H

H2C C

CH2CHCH3

Cl

H

C C

Cl

H

H

CH2CH2CH3

H2C C

CHCH2CH3

Cl

H

H2C C

Cl

CH2CH2CH3


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Chapter 6 Chirality

64

10. What is the relationship between these two structures? (Sec. 6.3, 6.5)

a) Identical structuresb) Enantiomers

c) Diastereomers

d) Constitutional isomers

11. What is the relationship between these two structures? (Sec. 6.3, 6.5)

a) identical structures

b) enantiomersc) diastereomers

d) constitutional isomers

CH3

NH2H

CH3H

NH2

H

CH3H2N

NH2H3C

H

H

Br Cl

H H

Br

Cl

H


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Chapter 6 Chirality

65

12. Which are meso compounds? (Sec. 6.5)

a) I, II

b) I, III

c) II, IIId) III, IV

13. How many stereoisomers are possible for Prilosec? (Sec. 6.7)

NNH

O

CH3

CH3

O OH

.HCl

a) 4

b) 8c) 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.


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Chapter 6 Chirality

66

14. How many pairs of enantiomers are possible for cortisone acetate? (Sec. 6.7)

O

CH3

O CH

3 O

O

OOH

a) 32

b) 64c) 128

d) 256

15. Which forms of lactic acid are R forms? (Sec. 6.4)

a) I, II

b) III, IV

c) I, III

d) II, IV

16. What is the R,S configuration for the following structure of isocitric acid? (Sec. 6.4)

a) 2-R, 3-Rb) 2-R, 3-S

c) 2-S, 3-R

d) 2-S, 3-S

COH

HH3CO

O

CH3

OHHOC

H

O

COH

CH3HHO

O

CH3

COHHOH

O

I. II. III. IV.

C

CCOH

OCCH2

H

HCOH

HO

O

O

O

#1


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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, IVb) 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, Id) IV, I, II, III

OH Cl CH3 H

I. II. III. IV.

IV.III.II.I.

C C

H

H

H

OH OCH3 C O

H

OCH3 COH

O

CH

O

OCH2CH3

IV.III.II.I.


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Chapter 6 Chirality

68


a) III, II, IV, I

b) IV, I, II, IIIc) I, III, II, IV

d) IV, II, I, III

22. Which structures represent R-3-methylhexane? (Sec. 6.4)

a) II, IIIb) 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 C

H

H

H

C CH3

CH3

CH3

C H

CH3

CH3

C C

H3C

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


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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, IIb) II, III

c) II, IV

d) III, IV

Fill in the Blank

1. The following structure contains ___________ stereocenters. (Sec. 6.7)

OH

OH

O

N

OH

Nadolol (beta-blocker)

2. The following structure contains __________ stereocenters. (Sec. 6.7)

O OH

N

CH3

morphine

3. The priority order for the following groups are (highest = 1),

C

CH3

CH3CH

3

C C

CH3

H

H

C C H C

CH3

HCH

3

(Sec. 6.4)


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Chapter 6 Chirality

70

4. The priority order for the following groups is (highest = 1),

C

Cl

Cl

CH3

C

Br

H

CH3

C

Cl

OH

CH3

C

OH

H

CH3

(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)


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Chapter 6 Chirality

71

9. The following structures are __________________ (what type of stereoisomer). (Sec. 6.3, 6.5)

NH2

OH NH2

OH

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

CH3OH

Cl

Cl

CH3OH

H

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> > >


76/288

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)


77/288

Chapter 6 Chirality

73

Answers

Multiple Choice

1. d2. b

3. d

4. c5. c

6. c

7. d

8. d9. a

10. a

11. c

12. c13. b

14. a

15. a16. b

17. c18. d

19. b20. d

21. d

22. c

23. c

24. d25. c

Fill in the Blank

1. 3

2. 53. 2, 3, 1, 44. 2, 1, 3, 4

5. 2R, 3R

6. 1S, 2S

7.

OH

OH

8.

Br

Cl

9. enantiomers

10. diastereomers


78/288

Chapter 6 Chirality

74

True-False

1. T

2. T

3. F4. T

5. F

6. F7. T

8. F

9. F

10. T


79/288

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, IIId) II, IV

2. Which of the following structures have correct common names? (Sec. 7.2)

a) I, IIb) III, IV

c) I, IIId) II, IV

C

Cl

CH3

CH2CH2CH3H

CH3

F

OCH3H

Br

Br

HH3CO

C

CH3

CH2CH3

FCl

R-2-chloropentaneI

R-4-fluoro-4-methylcyclohexeneII

meso-1,2-dibromo-1,2-dimethoxyethaneIII

S-2-chloro-2-fluorobutanIV

H2C CHCH

2F

CHCH2Br

H3C

H3C

HCCl3 H3C CH

I

CH2CH3

allyl fluorideI

isobutyl bromideII

methylene chlorideIII

isopropyl iodideIV


80/288


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, IIId) I, IV

4. Which compounds are primary halides? (Sec. 7.6)

a) I, IIb) III, IV

c) II, IIId) 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/ CCl4b) HI

c) NaI

d) HIO4

3C 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)


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77

7. Arrange the nucleophiles in order of increasing reactivity (least first). (Sec. 7.6)

a) I, IV, II, III

b) IV, II, I, IIIc) 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, IIId) 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

BrH3CO3CCO

O

HO

I II III IV

ICl Br F

IVIIIIII

IVIIIIII

CH3OOHH2ONH3


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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, IVd) 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, IVd) 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


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79

13. Which nucleophilic substitution reactions will proceed? (Sec. 7.6-7.7)

a) I, II

b) II, IIIc) III, IV

d) I, IV

14. Which reactions will proceed with inversion of configuration? (Sec. 7.6-7.7)

a) I, II

b) III, IVc) 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, IVc) 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


84/288


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, IVc) 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) ethanolII) hexane

III) DMSO

IV) water

a) III, IV

b) II, III

c) I, IVd) I, III

IVIIIIII

CH3CH2CH2ClCHCl

H3CH2C

H3CH2CCHCl

H3C

H3C

CCl

CH3

H3C

CH3

d)

c)

b)

a)

NaCN

NaSH

CH3OH

NaCN

DMSO

DMSO

H2O

acetone

+

+

+

+

CCl

CH3

H3CCH3

CH3CH2CH2Br

CHCl

H3C

H3C

CH3CH2Cl


85/288


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, IVd) 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, IIb) III, IV

c) I, IVd) 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-penteneb) 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


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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, IVd) II, IV

25. Which conditions are best for preparing isopropyl methyl ether? (Sec. 7.10)

CH2

Cl CH3CH3

Cl

CH2Cl

CH3

Cl

a) b) c) d)

d)

c)

b)

a)

acidcatalysis

heat

+

+

+

+

CHOH

H3C

H3C

CHBr

H3C

H3C

CH3Br

CHBrH3C

H3C

CH3OH

CH3OH

Na OCH

CH3

CH3

Na OCH3


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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)


I

NaOCH2CH3

CH3CH2OH (Sec. 7.9)


H Br

H2O

(Sec. 7.6)

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

Cl (Sec. 7.9)


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84


BrH OHH

(racemic)

(Sec. 7.6)


HBrHH3CO H OCH3

+

(Sec. 7.6)

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

I

KI

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 > > >


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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)

Cl

Br

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)


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86

Answers

Multiple Choice

1. c2. a

3. c

4. b5. a

6. b

7. c8. b

9. c

10. a

11. d

12. d13. b

14. a

15. c16. a

17. b18. c

19. b20. a

21. b

22. c

23. c

24. a25. b

Fill in the Blank

1.

H SCH3

2.

OHH

3.

HNH2


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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. F4. T

5. F6. F

7. T

8. T

9. T10. F


92/288

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)

O

CH2

O

CH2

OH

C

CH3

H OCH3

CH3

CH

CH3

OCH3

OH

OH

cis-1,2-dimethoxycyclohexane I

R-2-methoxy-1-propanol II

2-methoxypropane III

trans-1,3-cyclohexanediol IV

a) I, II

b) III, IV

c) II, III

d) I, IV

3. Arrange the compounds in the order of increasing solubility in water (least first). (Sec. 8.4)

a) I, III, II, IV

b) III, I, IV, IIc) I, IV, II, III

d) IV, I, III, II

OH

IVIII

III

CH3CH2CH2CH2CH2OHCH3OCH2CH2OCH3

CH3OCH3CH3CH2CH2CH2OCH3


93/288


89

4. Which are secondary alcohols? (Sec. 8.2)

a) I, III

b) II, III

c) III, IVd) I, IV

5. Arrange the compounds in the order of increasing acidity (least first). (Sec. 8.3)

a) III, I, II, IVb) 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, IVb) I, IV, II, III

c) III, II, I, IV

d) II, I, IV, III

CH3

OH

CH3C

CH3

CH3

OH C C

H3C

H

H

CHCH3

OH

H OH

I II III IV

IVIIIIII

H2OCH3CHCH3

OHCH3COH

CH3

CH3CH3CH2OH

IVIIIIII

H2OH2SCH3CH2SHCHOH

3C

3C


94/288


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, IIIc) 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, Ic) III, IV, II, I

d) II, IV, III, I

9. Which alcohol will form the most stable carbocation? (Sec. 8.3)

IVIIIIII

CH3CH2SHCH3CH2OHH2O3C

OCH3

d)

c)

b)

a)

CH3OH

OH

COH

CH3

CH3

CH3

CH3CHCH2OHCH3


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10. How many isomers, including stereoisomers, can be formed from the hydroxylation of 4-

methylcyclohexene using osmium tetroxide? (Sec. 8.3, 8.4)

a) 2b) 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, IVb) 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, IIIc) II, IV

d) I, III

13. Which is the major product from the acid catalyzed hydrolysis of cyclohexene oxide? (Sec. 8.5)

O 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.


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92

14. Which is the major product of the following reaction? (Sec. 8.5)

C C

O

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 H3PO4COOH

O

heat

dilute dilute

heat

a) b)

c) d)

OHH3PO4 OsO4/ ROOH

heat

CH3CHCH3

OH

CH3CH2CH2OH

d)c)

b)a)

O

H

H

O

O

OH

OH

OH


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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

O

OH

OH O

O

Oa) b) c) d)

H3PO4

heat

HCl SOCl2

K Cl2 NaCl

a) b)

c) d)

heat

Pt / H2H3PO4CH3CHCH2OH

CH3

d)c)

b)a)

CH3CH2CH2CH3CH3CHCH3

CH3

CH3CHCOH

CH3

O

CH3CHCHCH3

O


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22. Which is the major product of the following reaction? (Sec. 8.3, 8.5)

23. Arrange the following in order of increasing rate of reactivity with HBr (least first). (Sec. 8.3)

a) I, II, IV, III

b) II, I, III, IV

c) IV, III, I, IId) III, II, IV, I

24. Classify the following reaction. (Sec. 8.6)

a) oxidation

b) reduction

c) neitherd) both

3C

COOH

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

OOH

C CH

O O

a) b) c) d)

IVIIIIII

CH3OH

CH2OHOH

CH3

OH

2 CH3CH2SHCH3CH2S SCH2CH3


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a) 3-pentanolb) 2-pentanol

c) 2-methyl-2,3-pentanediol

d) 4-methyl-3,4-pentanediol

Fill in the Blank


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,

O

H2NCH3

(Sec. 8.5)


OH O (Sec. 8.3)

C CH

O

CH2CH33C

H3C

H+/ H2O


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96


OH Cl (Sec. 8.3)


O

(Sec. 8.5)


H3PO4

heat (Sec. 8.3)


Cl

SOCl2

(Sec. 8.3)

10. The reaction arrows (curved arrows) required to complete the following reaction mechanisms are,

OH

H SO4

H O+

HH

C+

HH

HH

SO4

H-

(Sec. 8.3)


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True-False

1. The strongest acid in the following list is water. (Sec. 8.3, 8.4, 8.6)

CH3

OCH

3CH

3

SCH

3 HO

H 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)

Cl

OH

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)

CH3CH

2

OHCH3

OH CH

3CH

2CH

2

OH CH3CH2CH2CH2

OH> > >

8. The following compounds are listed in decreasing boiling point order (highest first). (Sec. 8.2, 8.4)

CH3

OCH

3 HO

HCH3

OH> >

9. The following compounds are listed in decreasing order of solubility in water (highest first). (Sec. 8.2)

CH3CH

2

OH CH

3

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<


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98

Answers

Multiple Choice

1. b2. b

3. c

4. c5. c

6. b

7. d8. b

9. b

10. a

11. a

12. c13. b

14. d

15. a16. a

17. b18. c

19. c20. b

21. d

22. a

23. c

24. b25. c

Fill in the Blank

1.

2.

O

OH

3.

O Na+

4.

OH

NHCH3

5. PCC


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99

6. SOCl2

7. a peracid

8.

OH

9.

OH

10.

OHH SO

4H O

+

HH

C+

HH

HH

SO4H

-

True-False

1. F2. F

3. T

4. F

5. F

6. T7. F

8. F

9. F

10. F


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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, IVc) I, IV

d) II, III

CH3

Br

CH3

Cl

Br

NO2

Cl

OCH3

CH2CH3

I. 2-bromotoluene II.para methyl, metachloro bromobenzene

III. metachloroaniline IV.paraethylanisole


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2. Which of the named compounds have correct structures? (Sec. 9.4)

CH3

Cl CH2CH

2Br

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, IVc) 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 -orbital electrons are in the following molecule? (Sec. 9.3)

a) 4

b) 6c) 8

d) 10

N

N

H


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5. Which structures are aromatic? (Sec. 9.3)

a) II, IIIb) 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, IVc) IV, II, I, III

d) IV, II, III, I

O

CH2

N O

O

I II III IV

IVIIIIII

OHNO2

NO2

OH

NO2

OH

Cl

OH


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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) 2c) 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

O

H2CO3

OHOH


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1

b. organic chemistry brown 3e test bank

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