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TitleOrganic Chemistry/Fourth Edition
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LanguageEnglish
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Total Pages1275
Table of Contents
                            ORGANIC CHEMISTRY
ABOUT THE AUTHOR
BRIEF CONTENTS
CONTENTS
PREFACE
ACKNOWLEDGMENTS
A GUIDE TO USING THIS TEXT
INTRODUCTION
CHAPTER 1 CHEMICAL BONDING
CHAPTER 2 ALKANES
CHAPTER 3 CONFORMATIONS OF ALKANES AND CYCLOALKANES
CHAPTER 4 ALCOHOLS AND ALKYL HALIDES
CHAPTER 5 STRUCTURE AND PREPARATION OF ALKENES: ELIMINATION REACTIONS
CHAPTER 6 REACTIONS OF ALKENES: ADDITION REACTIONS
CHAPTER 7 STEREOCHEMISTRY
CHAPTER 8 NUCLEOPHILIC SUBSTITUTION
CHAPTER 9 ALKYNES
CHAPTER 10 CONJUGATION IN ALKADIENES AND ALLYLIC SYSTEMS
CHAPTER 11 ARENES AND AROMATICITY
CHAPTER 12 REACTIONS OF ARENES: ELECTROPHILIC AROMATIC SUBSTITUTION
CHAPTER 13 SPECTROSCOPY
CHAPTER 14 ORGANOMETALLIC COMPOUNDS
CHAPTER 15 ALCOHOLS, DIOLS, AND THIOLS
CHAPTER 16 ETHERS, EPOXIDES, AND SULFIDES
CHAPTER 17 ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION TO THE CARBONYL GROUP
CHAPTER 18 ENOLS AND ENOLATES
CHAPTER 19 CARBOXYLIC ACIDS
CHAPTER 20 CARBOXYLIC ACID DERIVATIVES: NUCLEOPHILIC ACYL SUBSTITUTION
CHAPTER 21 ESTER ENOLATES
CHAPTER 22 AMINES
CHAPTER 23 ARYL HALIDES
CHAPTER 24 PHENOLS
CHAPTER 25 CARBOHYDRATES
CHAPTER 26 LIPIDS
CHAPTER 27 AMINO ACIDS, PEPTIDES, AND PROTEINS. NUCLEIC ACIDS
APPENDIX 1
APPENDIX 2
APPENDIX 3
CREDITS
GLOSSARY
INDEX
WHERE TO FIND IT
Periodic Table of the Elements
                        
Document Text Contents
Page 2

ORGANIC CHEMISTRY, FOURTH EDITION

Copyright © 2000, 1996, 1992, 1987 by The McGraw-Hill Companies, Inc. All rights reserved. Printed in the
United States of America. Except as permitted under the United States Copyright Act of 1976, no part of this
publication may be reproduced or distributed in any form or by any means, or stored in a data base or retrieval
system, without the prior written permission of the publisher.

This book is printed on acid-free paper.

1 2 3 4 5 7 8 9 0 VNH/VNH 9 0 9 8 7 6 5 4 3 2 1 0 9

ISBN 0-07-290501-8

Vice president and editorial director: Kevin T. Kane
Publisher: James M. Smith
Sponsoring editor: Kent A. Peterson
Developmental editor: Terrance Stanton
Editorial assistant: Jennifer Bensink
Senior marketing manager: Martin J. Lange
Senior marketing assistant: Tami Petsche
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Designer: K. Wayne Harms
Photo research coordinator: John C. Leland
Senior supplement coordinator: David A. Welsh
Compositor: GTS Graphics, Inc.
Typeface: 10/12 Times Roman
Printer: Von Hoffmann Press, Inc.

Cover/interior designer: Jamie O’Neal
Photo research: Mary Reeg Photo Research

The credits section for this book begins on page C-1 and is considered an extension of the copyright page.

Library of Congress Cataloging-in-Publication Data

Carey, Francis A.
Organic chemistry / Francis A. Carey. — 4th ed.

p. cm.
Includes index.
ISBN 0-07-290501-8 — ISBN 0-07-117499-0 (ISE)

1. Chemistry, Organic. I. Title.

QD251.2.C364 2000
547—dc21 99-045791

CIP

INTERNATIONAL EDITION ISBN 0-07-117499-0
Copyright © 2000. Exclusive rights by The McGraw-Hill Companies, Inc. for manufacture and export. This
book cannot be re-exported from the country to which it is consigned by McGraw-Hill. The International
Edition is not available in North America.

www. mhhe.com

McGraw-Hill Higher Education
A Division of The McGraw-Hill Companies

Page 637

The chemical shift of the hydroxyl proton signal is variable, depending on solvent,
temperature, and concentration. Its precise position is not particularly significant in struc-
ture determination. Because the signals due to hydroxyl protons are not usually split by
other protons in the molecule and are often rather broad, they are often fairly easy to
identify. To illustrate, Figure 15.5 shows the 1H NMR spectrum of 2-phenylethanol, in
which the hydroxyl proton signal appears as a singlet at � 4.5 ppm. Of the two triplets
in this spectrum, the one at lower field strength (� 4.0 ppm) corresponds to the protons
of the CH2O unit. The higher-field strength triplet at � 3.1 ppm arises from the benzylic
CH2 group. The assignment of a particular signal to the hydroxyl proton can be con-
firmed by adding D2O. The hydroxyl proton is replaced by deuterium, and its

1H NMR
signal disappears.
13C NMR: The electronegative oxygen of an alcohol decreases the shielding of the car-
bon to which it is attached. The chemical shift for the carbon of the C±OH unit is
60–75 ppm for most alcohols. Compared with an attached H, an attached OH causes a
downfield shift of 35–50 ppm in the carbon signal.

CH3CH2CH2CH3

Butane 1-Butanol

CH3CH2CH2CH2OH

� 13.0 ppm � 61.4 ppm

H C O H

� 3.3–4.0 ppm � 0.5–5 ppm

606 CHAPTER FIFTEEN Alcohols, Diols, and Thiols

Wave number, cm�1

T
ra

ns
m

it
ta

nc
e

(%
)

O±H C±H

OH
W

C±O

FIGURE 15.4 The in-
frared spectrum of cyclo-
hexanol.

Page 1275

1

H
1.008

2

He
4.003

3

Li
6.941

4

Be
9.012

11

Na
22.99

12

Mg
24.31

19

K
39.10

20

Ca
40.08

37

Rb
85.47

38

Sr
87.62

55

Cs
132.9

56

Ba
137.3

87

Fr
(223)

88

Ra
(226)

21

Sc
44.96

22

Ti
47.88

39

Y
88.91

40

Zr
91.22

71

Lu
175.0

72

Hf
178.5

103

Lr
(260)

104

Rf
(261)

23

V
50.94

24

Cr
52.00

41

Nb
92.91

42

Mo
95.94

73

Ta
180.9

74

W
183.9

105

Db
(262)

106

Sg
(266)

25

Mn
54.94

26

Fe
55.85

43

Tc
(98)

44

Ru
101.1

75

Re
186.2

76

Os
190.2

107

Bh
(262)

108

Hs
(265)

27

Co
58.93

45

Rh
102.9

77

Ir
192.2

109

Mt
(266)

57

La
138.9

58

Ce
140.1

60

Nd
144.2

61

Pm
(145)

62

Sm
150.4

63

Eu
152.0

59

Pr
140.9

89

Ac
(227)

90

Th
232.0

92

U
238.0

93

Np
(237)

94

Pu
(242)

95

Am
(243)

91

Pa
(231)

28

Ni
58.69

29

Cu
63.55

46

Pd
106.4

47

Ag
107.9

78

Pt
195.1

79

Au
197.0

30

Zn
65.39

48

Cd
112.4

80

Hg
200.6

64

Gd
157.3

65

Tb
158.9

67

Ho
164.9

68

Er
167.3

69

Tm
168.9

70

Yb
173.0

66

Dy
162.5

96

Cm
(247)

97

Bk
(247)

99

Es
(252)

100

Fm
(257)

101

Md
(258)

102

No
(259)

98

Cf
(251)

31

Ga
69.72

32

Ge
72.61

49

In
114.8

50

Sn
118.7

81

Tl
204.4

82

Pb
207.2

33

As
74.92

51

Sb
121.8

83

Bi
209.0

34

Se
78.96

35

Br
79.90

52

Te
127.6

53

I
126.9

84

Po
(209)

85

At
(210)

36

Kr
83.80

54

Xe
131.3

86

Rn
(222)

5

B
10.81

6

C
12.01

13

Al
26.98

14

Si
28.09

7

N
14.01

15

P
30.97

8

O
16.00

9

F
19.00

16

S
32.07

17

Cl
35.45

10

Ne
20.18

18

Ar
39.95

3

4

5

6

7

3B
(3)

4B
(4)

5B
(5)

6B
(6)

7B
(7) (9) (10)

1B
(11)

2B
(12)

3A
(13)

4A
(14)

5A
(15)

6A
(16)

7A
(17)

8A
(18)

2

1

6

7

(8)

1A
(1)

2A
(2)

8B

Lanthanides

Actinides

TRANSITION ELEMENTS

INNER TRANSITION ELEMENTS

MAIN–GROUP
ELEMENTS

MAIN–GROUP
ELEMENTS

P
e
ri
o
d

110 111 112

(269) (272) (277)

Metals (main-group)
Metals (transition)
Metals (inner transition)
Metalloids
Nonmetals

Periodic Table of the Elements

As of mid-1999, elements 110 through 112 have not yet
been named.

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