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Periodic Table of Elements
KEY
Group number,
U.S. system
IUPAC system
Period
number

79

1A
(1)

Au

2A
(2)

Gold

196.9665

1

Atomic number
Symbol
Name
Atomic mass

Metals
Semimetals
8A
(18)

Nonmetals

An element

H

2

1 Hydrogen

3A
(13)

1.0079
3

2

7

8

7A
(17)

9

He
Helium

10

Be

B

C

N

O

F

Ne

Boron

Carbon

Nitrogen

Oxygen

Fluorine


Neon

6.941

9.0122

10.811

12.011

14.0067

15.9994

18.9984

20.1797

Mg
Magnesium

22.9898

24.3050

19

39.0983
37


Rb

5 Rubidium
85.4678
55

13

12

Na
Sodium

20

3B
(3)

4B
(4)

21

5B
(5)

22

23


Ca

Sc

Ti

V

Calcium

Scandium

Titanium

Vanadium

40.078

44.9559

47.88

50.9415

38

39

40


41

Sr

Y

Zr

Nb

Strontium

Yttrium

Zirconium

Niobium

87.62

88.9059

91.224

92.9064

56

57


72

73

6B
(6)

7B
(7)

8B
(8)

8B
(9)

15

16

17

P

S

Cl

Ar


Phosphorus

Sulfur

Chlorine

Argon

26.9815

28.0855

30.9738

32.066

35.4527

39.948

Co

Ni

Cu

Zn

Ga


Ge

As

Se

Br

Kr

Iron

Cobalt

Nickel

Copper

Zinc

Gallium

Germanium

Arsenic

Selenium

Bromine


Krypton

55.847

58.9332

58.693

63.546

65.39

69.723

72.61

74.9216

78.96

79.904

83.80

42

43

44


Tc

Ru

95.94
74

(98)
75

101.07
76

45

50

Ag

Cd

In

Sn

Sb

Te


I

Xe

Silver

Cadmium

Indium

Tin

Antimony

Tellurium

Iodine

Xenon

102.9055

106.42

107.8682

112.411

114.82


118.710

121.757

127.60

126.9045

131.29

81

82

83

52

84

53

85

Ba

La

Hf


Ta

W

Re

Os

Ir

Pt

Au

Hg

Tl

Pb

Bi

Po

At

Rn

Barium


Lanthanum

Hafnium

Tantalum

Tungsten

Rhenium

Osmium

Iridium

Platinum

Gold

Mercury

Thallium

Lead

Bismuth

Polonium

Astatine


Radon

132.9054

137.327

138.9055

178.49

180.9479

183.85

186.207

190.2

192.22

195.08

196.9665

200.59

204.3833

207.2


208.9804

(209)

(210)

(222)

87

88

89

Fr

Ra

Ac

Radium

Actinium

(223)

227.0278

(227)


104

105

Rf

Db

Rutherfordium Dubnium

(261)

(262)

106

107

108

Sg

Bh

Hs

Seaborgium

Bohrium


Hassium

(263)

(262)

(265)

109

110

111

112

114

Mt

Ds

Rg

—

—

—


—

—

(277)

(285)

(289)

Meitnerium Darmstadtium roentgenium

(266)

(271)

(277)

5

86

Cs
Cesium

Francium

4

54


49

Pd

80

51

3

36

Palladium

79

48

34

Rh

78

47

33

Rhodium


77

46

32

35

26

Fe

Mo

31

2

18

Si
Silicon

25

Molybdenum Technetium Ruthenium

30


14

Al
Aluminum

Mn
54.9380

29

2B
(12)

24

51.9961

28

1B
(11)

Cr

Chromium Manganese

27

8B
(10)


1

4.0026

Beryllium

K

7

6

6A
(16)

Li

4 Potassium

6

5

5A
(15)

Lithium

11


3

4

4A
(14)

6

116

—

7

Numbers in parentheses
are mass numbers of
radioactive isotopes.
58

Lanthanides

6

Ce
Cerium

140.115
90


Actinides

7

Th
Thorium

232.0381

59

60

61

62

Pr

Nd

Pm

Sm

Praseodymium Neodymium Promethium Samarium

140.9076


144.24

91

92

Pa

U

Protactinium Uranium

231.0359

238.0289

(145)

150.36

63

66

67

68

69


70

71

Tb

Dy

Ho

Er

Tm

Yb

Lu

Terbium

Dysprosium

Holmium

Erbium

Thulium

Ytterbium


Lutetium

151.965

157.25

158.9253

162.50

164.9303

167.26

168.9342

173.04

174.967

93

94

95

Np

Pu


Am

(244)

65

Gd
Gadolium

Neptunium Plutonium Americium

(237)

64

Eu
Europium

(243)

96

Cm
Curium

(247)

97

98


99

Bk

Cf

Es

Berkelium Californium Einsteinium

(247)

(251)

(252)

100

101

102

Fm

Md

No

Fermium Mendelevium Nobelium


(257)

(258)

(259)

6

103

Lr
Lawrencium

(260)

7


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Common Functional Groups
General
Formula

Example

Name

RH


CH3CH2CH3

Alkane (Alkanes have no functional group.)

RCHœCH2

CH3CH2CHœCH2

Alkene (The functional group is the carbon–carbon double bond.)

RCPCH

CH3CPCH

Alkyne (The functional group is the carbon–carbon triple bond.)

ArH

Arene (A six-membered ring with three double bonds has different reactions than an
alkene so it is given a different name. Arenes or aromatic rings can have alkyl or
other groups attached to the ring.)

RX

CH3CH2CH2Cl

Alkyl halide (The functional group is the carbon–halogen bond.)

ROH


CH3CH2OH

Alcohol (The functional group is the C±O±H.)

ROR

CH3CH2OCH3

Ether (The functional group is the C±O±C . The alkyl groups on the O can be the
same or different.)

RNH2

CH3CH2CH2NH2

Amine (The C±N is the functional group. The other H’s on the N can be replaced
with alkyl groups.)

O
X
RCH

O
X
CH3CH2CH

O
X
RCR


O
X
CH3CCH3

O
X
RCOH

O
X
CH3CH2COH

O
X
Carboxylic acid (The functional group is the COH .)

O
X
RCCl

O
X
CH3CCl

O
X
Acyl chloride (The functional group is the CCl .)

O O

X X
RCOCR

O O
X X
CH3COCCH3

O O
X X
Acid anhydride (The functional group is the COC . The alkyl groups may be different.)

O
X
RCOR

O
X
CH3COCH2CH3

O
X
Ester (The functional group is the COC .)

O
X
RCNH2

O
X
CH3CH2CNHCH3


O
X
Amide (The functional group is the CN . The other groups on the N may be H’s or

Aldehyde (The functional group is the CœO with at least one H on the C.)

Ketone (The functional group is the CœO with two alkyl groups on the C. The alkyl
groups need not be the same.)

alkyl groups.)

RCPN

CH3CH2CH2CPN

Nitrile (The functional group is the carbon–nitrogen triple bond.)


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20 Enolate and
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20.5 Aldol Condensation

21 The Chemistry
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21.6 Halogenation

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22 Pericyclic
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27 Nucleotides and
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O R GA N I C C H E M I S T R Y
J OS E P H M . HOR N BAC K
UNIVERSITY OF DENVER

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in the United States)

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To Melani, Joe, Pat, Jordan, and Cullen,
who bring meaning and joy to my life.


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About the Author


J

oseph M. Hornback was born and raised in
southwestern Ohio. He received a B.S. in
Chemistry, magna cum laude, from the University of Notre Dame in 1965. He then attended the
Ohio State University on an NSF traineeship and received his Ph.D. in 1968. He next moved to the University of Wisconsin at Madison on an NIH
postdoctoral fellowship.
In 1970, he joined the faculty of the Department
of Chemistry at the University of Denver, where he
is now Professor of Chemistry and Biochemistry.
His research interests are in the areas of synthetic
organic chemistry and organic photochemistry. He
has served in a number of administrative positions,
including Associate Dean for Undergraduate Studies; Associate Dean for Natural Sciences, Mathematics, and Engineering; and Director of the
Honors Program. But his first love has always been teaching, and he has taught organic
chemistry nearly every term, even when he was in administration. He has received the
Natural Sciences Award for Excellence in Teaching and the Outstanding Academic Advising Award.
Joe is married and has three children, two sons and a daughter, and one grandson.
He enjoys sports and outdoor activities, especially fishing and golf.

x


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Brief Contents

1

A Simple Model for Chemical Bonds


2

Organic Compounds: A First Look

3

Orbitals and Bonding

4

The Acid–Base Reaction

5

Functional Groups and Nomenclature I

142

6

Stereochemistry I:
Cis–Trans Isomers and Conformations

178

1
30

9

10
11

Nuclear Magnetic Resonance
Spectroscopy 543

15

Ultraviolet-Visible Spectroscopy
and Mass Spectrometry 609

16

Benzene and Aromatic Compounds

17

Aromatic Substitution Reactions

18

Additions to the Carbonyl Group:
Reactions of Aldehydes and Ketones

61
103

642

671


739

19

Substitutions at the Carbonyl Group:
Reactions of Carboxylic Acids
and Derivatives 803

20

Enolate and Other Carbon Nucleophiles

21

The Chemistry of Radicals

22

Pericyclic Reactions

23

The Synthesis of Organic Compounds

24

Synthetic Polymers

348


25

Carbohydrates

Additions to Carbon–Carbon Double
and Triple Bonds:
Reactions of Alkenes and Alkynes 404

26

Amino Acids, Peptides, and Proteins

27

Nucleotides and Nucleic Acids

28

Other Natural Products

7 Stereochemistry II:
Chiral Molecules 219

8

14

Nucleophilic Substitution Reactions:
Reactions of Alkyl Halides, Alcohols,

and Related Compounds 257
Elimination Reactions:
Reactions of Alkyl Halides, Alcohols,
and Related Compounds 313
Synthetic Uses of Substitution
and Elimination Reactions:
Interconverting Functional Groups

12

Functional Groups and Nomenclature II

13

Infrared Spectroscopy

466

858

918

956
1011

1053

1085
1123


1162

1184

500
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Contents

Preface

1

xxvi

A Simple Model for Chemical Bonds
1.1
1.2
1.3
1.4
1.5
1.6
1.7
1.8
1.9
1.10
1.11


2

Organic Compounds: A First Look
2.1
2.2
2.3
2.4
2.5
2.6
2.7

3

1

30

Common Bonding Situations
30
Bond Strengths and Bond Lengths
33
Constitutional Isomers
34
Degree of Unsaturation
39
Physical Properties and Molecular Structure
44
Melting Points, Boiling Points, and Solubilities
46

48
Focus On: Boiling Points of Fuels
Introduction to Functional Groups
50
52
Review of Mastery Goals
Additional Problems
53

Orbitals and Bonding
3.1
3.2
3.3
3.4
3.5

xii

The Field of Organic Chemistry
Simple Atomic Structure
3
Ionic Bonding
4
Covalent Bonding
5
Lewis Structures
6
Covalent Ions
11
Formal Charges

11
Resonance
15
Polar Bonds
17
Shapes of Molecules
18
Dipole Moments
22
24
Review of Mastery Goals
Additional Problems
25

1

61

Atomic Orbitals
61
Molecular Orbitals
65
Single Bonds and sp3 Hybridization
Double Bonds and sp2 Hybridization
Triple Bonds and sp Hybridization

69
71
76



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CONTENTS

3.6
3.7
3.8
3.9

4

The Acid–Base Reaction
4.1
4.2
4.3
4.4
4.5
4.6
4.7
4.8
4.9
4.10

5

5.4
5.5
5.6
5.7

5.8
5.9
5.10

94

103

Definitions
103
The Acid–Base Equilibrium
107
Rate of the Acid–Base Reaction
111
Effect of the Atom Bonded to the Hydrogen on Acidity
Inductive Effects
116
Hydrogen Bonding
119
Hybridization
120
Resonance
120
121
Focus On: Calcium Carbide
Tables of Acids and Bases
128
Acidity and Basicity of Functional Groups
and Solvents
132

135
Review of Mastery Goals
Additional Problems
135

Functional Groups and Nomenclature I
5.1
5.2
5.3

6

Resonance and MO Theory
78
Rules for Resonance Structures
81
Types of Resonance Interactions
86
Focus On: Resonance and the Bond Lengths of Naphthalene
Molecular Orbital Energies
95
97
Review of Mastery Goals
Additional Problems
97

114

142


Alkanes
142
Common Nomenclature of Alkanes
145
Systematic Nomenclature of Alkanes
146
146
Focus On: The Energy Content of Fuels
Systematic Nomenclature of Cycloalkanes
155
Alkenes
157
Alkynes
160
Alkyl Halides
161
Alcohols
162
Focus On Biological Chemistry: Chlorinated Organic Compounds
Ethers
167
Amines
168
171
Review of Mastery Goals
Additional Problems
172

164


Stereochemistry I: Cis–Trans Isomers
and Conformations 178
6.1
6.2
6.3

Cis–Trans Isomers
179
Designating the Configuration of Cis–Trans Isomers
Conformations
186

183

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xiv

CONTENTS

6.4
6.5
6.6
6.7
6.8

7


Stereochemistry II: Chiral Molecules
7.1
7.2
7.3
7.4
7.5
7.6
7.7
7.8

7.9
7.10

8

Conformations of Cyclic Molecules
193
Conformations of Cyclohexane
196
Conformations of Other Rings
201
Conformations of Cyclohexanes with One Substituent
Conformations of Cyclohexanes with Two
or More Substituents
205
206
Focus On: How Much Strain Is Too Much?
Review of Mastery Goals
214

Additional Problems
214

202

219

Chiral Molecules
219
Recognizing Chiral Molecules
221
Designating Configuration of Enantiomers
224
Properties of Enantiomers
227
Molecules with Multiple Chirality Centers
230
Stereoisomers and Cyclic Compounds
234
Resolution: Separating Enantiomers
236
Fischer Projections
237
Focus On: The Historical Development of Understanding
238
Stereochemistry
Reactions That Produce Enantiomers
242
243
Focus On: Pharmaceuticals and Chirality

Other Chiral Compounds
244
247
Review of Mastery Goals
Visual Summary of Isomers
248
Additional Problems
249

Nucleophilic Substitution Reactions:
Reactions of Alkyl Halides, Alcohols,
and Related Compounds 257
8.1
8.2
8.3
8.4
8.5
8.6
8.7
8.8
8.9
8.10
8.11
8.12
8.13
8.14

The General Reaction
257
Reaction Mechanisms

259
Bimolecular Nucleophilic Substitution
259
261
Stereochemistry of the SN2 Reaction
Effect of Substituents on the Rate of the SN2 Reaction
Unimolecular Nucleophilic Substitution
268
Effect of Substituents on the Rate of the SN1 Reaction
274
Focus On: The Triphenylmethyl Carbocation
Stereochemistry of the SN1 Reaction
276
Leaving Groups
279
Nucleophiles
284
Effect of Solvent
286
289
Competition between SN1 and SN2 Reactions
Intramolecular Reactions
292
Competing Reactions
294

264
272



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CONTENTS

299

Focus On: Carbocation Rearrangements in Superacids
Review of Mastery Goals
301
Visual Summary of Key Reactions
301
Additional Problems
302

9

Elimination Reactions: Reactions of Alkyl
Halides, Alcohols, and Related Compounds
9.1
9.2
9.3
9.4
9.5
9.6

9.7

10

313


The General Reaction
313
Bimolecular Elimination
314
316
Focus On Biological Chemistry: DDT-Resistant Insects
Stereochemistry of the E2 Reaction
316
Direction of Elimination
323
Unimolecular Elimination
329
Regiochemistry and Stereochemistry
of the E1 Reaction
331
333
Focus On: The E1cb Mechanism
The Competition between Elimination and Substitution
334
Focus On Biological Chemistry: Biological Elimination
Reactions
340
Review of Mastery Goals
341
Visual Summary of Key Reactions
341
Additional Problems
341


Synthetic Uses of Substitution and Elimination
Reactions: Interconverting Functional Groups
10.1
10.2
10.3
10.4
10.5
10.6

10.7
10.8
10.9
10.10
10.11
10.12
10.13
10.14

10.15

348

Substitution Reactions
348
Preparation of Alcohols
349
Preparation of Ethers
352
Preparation of Esters
357

Preparation of Alkyl Halides
358
Preparation of Amines
362
Focus On Biological Chemistry:
365
Biological Alkylations and Poisons
Preparation of Hydrocarbons
368
Formation of Carbon–Carbon Bonds
369
Phosphorus and Sulfur Nucleophiles
371
Ring Opening of Epoxides
372
375
Focus On: Uses of Epoxides in Industry
Elimination of Hydrogen Halides
(Dehydrohalogenation)
376
Preparation of Alkynes
377
Dehydration
378
Eliminations to Form Carbon–Oxygen Double Bonds; Oxidation
Reactions
380
Focus On: Environmentally Friendly Chemistry
384
(Green Chemistry)

The Strategy of Organic Synthesis
385

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xvi

CONTENTS

Review of Mastery Goals
389
Visual Summary of Key Reactions
Integrated Practice Problem
394
Additional Problems
395

11

Additions to Carbon–Carbon Double and Triple Bonds:
Reactions of Alkenes and Alkynes 404
11.1
11.2
11.3
11.4
11.5
11.6

11.7
11.8
11.9
11.10
11.11
11.12
11.13
11.14

12

390

The General Mechanism
405
Addition of Hydrogen Halides
406
Addition of Water (Hydration)
412
Addition of Halogens
413
Halohydrin Formation
419
421
Focus On: Industrial Addition Reactions
Oxymercuration–Reduction
423
Hydroboration–Oxidation
426
433

Focus On: Chiral Boranes in Organic Synthesis
Addition of Carbenes
435
Epoxidation
438
Hydroxylation
439
Ozonolysis
441
Catalytic Hydrogenation
444
Additions of Conjugated Dienes
446
Focus On: Asymmetric Hydrogenation
449
Synthesis
451
453
Review of Mastery Goals
Visual Summary of Key Reactions
454
Integrated Practice Problem
457
Additional Problems
458

Functional Groups and Nomenclature II
12.1
12.2
12.3

12.4
12.5
12.6
12.7

466

Aromatic Hydrocarbons
466
469
Focus On: Structure Proof by the Number of Isomers
Phenols
472
Aldehydes and Ketones
473
Carboxylic Acids
477
Derivatives of Carboxylic Acids
479
486
Focus On: Fragrant Organic Compounds
Sulfur and Phosphorus Compounds
488
Nomenclature of Compounds with Several Functional
Groups
491
494
Review of Mastery Goals
Additional Problems
494



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CONTENTS

13

Infrared Spectroscopy
13.1
13.2
13.3
13.4
13.5
13.6
13.7
13.8
13.9
13.10

14

Electromagnetic Radiation
501
Interaction of Electromagnetic Radiation
with Molecules
502
The Electromagnetic Spectrum
503
Infrared Spectroscopy

505
Generalizations
507
The Hydrogen Region
508
The Triple-Bond Region
515
Focus On: Remote Sensing of Automobile Pollutants
The Double-Bond Region
518
The Fingerprint Region
520
Interpretation of IR Spectra
521
533
Review of Mastery Goals
Additional Problems
533

Nuclear Magnetic Resonance Spectroscopy
14.1
14.2
14.3
14.4
14.5
14.6
14.7
14.8
14.9
14.10


15

500

516

543

Proton Magnetic Resonance Spectroscopy
543
545
Theory of 1H-NMR
The Chemical Shift
547
Spin Coupling
556
Complex Coupling
562
Chemical Exchange
563
Deuterium
563
565
Focus On: NMR Spectroscopy of Carbocations in Superacid
1
Interpretation of H-NMR Spectra
566
572
Focus On: Magnetic Resonance Imaging

Carbon-13 Magnetic Resonance Spectroscopy
574
Solved Problems Employing IR and NMR Spectra
583
595
Review of Mastery Goals
Additional Problems
596

Ultraviolet-Visible Spectroscopy
and Mass Spectrometry 609
15.1
15.2
15.3
15.4
15.5
15.6

Ultraviolet-Visible Spectroscopy
609
Types of Electronic Transitions
612
UV-Visible Spectroscopy in Structure Determination
Focus On: Ozone, Ultraviolet Radiation, and Sunscreens
Mass Spectrometry
617
Determining the Molecular Formula
619
Fragmentation of the Molecular Ion
624

Focus On: Gas Chromatography and Mass Spectrometry
Review of Mastery Goals
634
Additional Problems
634

615
616

633

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xviii

CONTENTS

16

Benzene and Aromatic Compounds
16.1
16.2
16.3
16.4
16.5
16.6
16.7

16.8
16.9
16.10
16.11

17

17.8
17.9
17.10
17.11
17.12
17.13
17.14

18

Benzene
642
Resonance Energy of Benzene
644
Molecular Orbital Model for Cyclic Conjugated Molecules
646
Cyclobutadiene
649
Hückel’s Rule
651
Cyclooctatetraene
652
Heterocyclic Aromatic Compounds

653
Polycyclic Aromatic Hydrocarbons
655
657
Focus On: Carcinogenic Polycyclic Aromatic Hydrocarbons
NMR and Aromaticity
657
Annulenes
659
Aromatic and Antiaromatic Ions
661
663
Focus On: Buckminsterfullerene, a New Form of Carbon
Review of Mastery Goals
665
Additional Problems
665

Aromatic Substitution Reactions
17.1
17.2
17.3
17.4
17.5
17.6
17.7

642

671


Mechanism for Electrophilic Aromatic Substitution
671
Effect of Substituents
674
Effect of Multiple Substituents
682
Nitration
683
Halogenation
686
Sulfonation
689
Friedel-Crafts Alkylation
690
694
Focus On: Synthetic Detergents, BHT, and BHA
Friedel-Crafts Acylation
696
Electrophilic Substitutions of Polycyclic Aromatic
Compounds
699
Nucleophilic Aromatic Substitution: Diazonium Ions
700
Nucleophilic Aromatic Substitution: Addition–Elimination
703
Nucleophilic Aromatic Substitution: Elimination–Addition
705
708
Focus On: Experimental Evidence for the Benzyne Mechanism

Some Additional Useful Reactions
709
Synthesis of Aromatic Compounds
713
719
Review of Mastery Goals
Visual Summary of Key Reactions
719
Integrated Practice Problem
723
Additional Problems
724

Additions to the Carbonyl Group:
Reactions of Aldehydes and Ketones
18.1
18.2

739

General Mechanisms
740
Addition of Hydride; Reduction of Aldehydes
and Ketones
742


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CONTENTS


18.3
18.4
18.5
18.6
18.7
18.8
18.9
18.10
18.11

19

Substitutions at the Carbonyl Group:
Reactions of Carboxylic Acids and Derivatives
19.1
19.2
19.3
19.4
19.5
19.6
19.7
19.8
19.9
19.10
19.11

20

Addition of Water

744
Addition of Hydrogen Cyanide
748
Preparation and Properties of Organometallic
Nucleophiles
751
Addition of Organometallic Nucleophiles
753
Addition of Phosphorus Ylides; The Wittig Reaction
763
Focus On: Synthesis of Vitamin A
Addition of Nitrogen Nucleophiles
765
Focus On Biological Chemistry: Imines in Living Organisms
Addition of Alcohols
775
Conjugate Additions
779
Synthesis
784
787
Review of Mastery Goals
Visual Summary of Key Reactions
787
Integrated Practice Problem
789
Additional Problems
790

The General Mechanism

803
Preparation of Acyl Chlorides
808
Preparation of Anhydrides
810
Preparation of Esters
811
Preparation of Carboxylic Acids
815
819
Focus On: The Preparation of Soap
Preparation of Amides
824
Reaction with Hydride Nucleophiles
826
Reduction of Acid Derivatives to Aldehydes
830
Reactions with Organometallic Nucleophiles
832
Preparation of Ketones
834
Derivatives of Sulfur and Phosphorus Acids
836
Focus On Biological Chemistry: Nerve Gases and Pesticides
Review of Mastery Goals
840
Visual Summary of Key Reactions
840
Integrated Practice Problem
843

Additional Problems
843

Enolate and Other Carbon Nucleophiles
20.1
20.2
20.3
20.4
20.5

20.6

858

Enols and Enolate Anions
859
Halogenation of the ␣-Carbon
862
Alkylation of Enolate Anions
864
Alkylation of More Stabilized Anions
867
The Aldol Condensation
873
Focus On Biological Chemistry: The Reverse Aldol Reaction
880
in Metabolism
Ester Condensations
880


758

773

803

838

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xx

CONTENTS

20.7
20.8
20.9
20.10
20.11

21

The Chemistry of Radicals
21.1
21.2
21.3
21.4

21.5
21.6
21.7
21.8

21.9
21.10

22

Focus On: An Industrial Aldol Reaction
886
Carbon and Hydrogen Leaving Groups
887
Enamines
889
Other Carbon Nucleophiles
891
Conjugate Additions
894
Synthesis
898
902
Review of Mastery Goals
Visual Summary of Key Reactions
902
Integrated Practice Problem
904
Additional Problems
905


Radicals
918
Stability of Radicals
919
Geometry of Carbon Radicals
921
Generation of Radicals
922
General Radical Reactions
923
926
Focus On: The Triphenylmethyl Radical
Halogenation
927
Dehalogenation
934
Autoxidation
935
Focus On Biological Chemistry: Vitamin E
937
and Lipid Autoxidation
Radical Additions to Alkenes
939
Reductions and Radical Anions
941
946
Review of Mastery Goals
Visual Summary of Key Reactions
947

Additional Problems
948

Pericyclic Reactions
22.1
22.2
22.3
22.4
22.5
22.6
22.7
22.8
22.9

22.10

918

956

Pericyclic Reactions
956
MO Theory for Conjugated Molecules
959
Electrocyclic Reactions
965
Examples of Electrocyclic Reactions
970
973
Focus On: Dewar Benzene

Cycloaddition Reactions
975
The Diels-Alder Reaction
977
Other Cycloaddition Reactions
984
Sigmatropic Rearrangements
986
Examples of Sigmatropic Rearrangements
990
Focus On Biological Chemistry: Pericyclic Reactions
993
and Vitamin D
Rearrangements to Electron-Deficient Centers
994
999
Review of Mastery Goals
Visual Summary of Key Reactions
999
Additional Problems
1001


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CONTENTS

23

The Synthesis of Organic Compounds

23.1
23.2
23.3
23.4
23.5
23.6
23.7
23.8

24

24.4
24.5
24.6
24.7
24.8
24.9
24.10

25

Protecting Groups for Alcohols
1011
Protecting Groups for Aldehydes and Ketones
1015
Protecting Groups for Carboxylic Acids
1016
Protecting Groups for Amines
1018
Retrosynthetic Analysis

1020
1025
Focus On Biological Chemistry: Pheromones
Examples of Syntheses
1026
Reactions That Form Carbon–Carbon Bonds
1029
Preparation of Functional Groups
1030
1045
Review of Mastery Goals
Additional Problems
1046

Synthetic Polymers
24.1
24.2
24.3

25.5
25.6
25.7
25.8

1053

Radical Chain Polymerization
1053
Structures of Polymers
1057

Ionic Polymerization
1060
1062
Focus On: Super Glue
Coordination Polymerization
1062
Physical Properties of Polymers
1064
Major Thermoplastic Addition Polymers
1066
Elastomers
1068
Condensation Polymers
1070
Thermoset Polymers
1075
Chemical Properties of Polymers
1077
1080
Focus On: Recycling Plastics
Review of Mastery Goals
1081
Additional Problems
1081

Carbohydrates
25.1
25.2
25.3
25.4


1011

1085

Structures of Carbohydrates
1085
Stereochemistry of Carbohydrates
1086
Cyclization of Monosaccharides
1090
Reactions of Monosaccharides
1094
1095
Focus On: The Determination of Anomer Configuration
Focus On: Artificial Sweeteners
1103
Fischer’s Structure Proof for Glucose
1105
Disaccharides
1110
Polysaccharides
1111
Other Carbohydrate-Containing Compounds
1113
1115
Focus On Biological Chemistry: Blood Groups
Review of Mastery Goals
1116
Additional Problems

1117

xxi