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Sách giải cuốn Organic Structures from Spectra 4th Wiley (2007)

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Please Keep Absolutely
Confidential

ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman

Copyright: Copying or duplicating
these solutions in any form is
strictly prohibited

Solutions Manual

December 2007

1


Please Keep Absolutely
Confidential

ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman
5

1

Copyright: Copying or duplicating
these solutions in any form is
strictly prohibited

9



BrCH2 CH2Br

O

13

OH OH
CH3

C

C

Cl2CH CH3

CH3

CH3 CH3

2

2-butanone

1,2-dibromoethane

pinacol

1,1-dichloroethane


C4H8O

C2H4Br2

C6H14O2

C2H4Cl2

CH3CH2

OH

6

10

O
CH3

O

O

O

14

CH3
H


CH3

CH3
OH

O

propionic acid

1,2-butanedione
(biacetyl)
C4H6O2

C3H6O2

3

O
CH2CH3
CH3

4

7

O

CH2C

N


CH2C

N

11

1,4-cyclohexanedione

2-propanol

C6H8O2

C3H8O

O

15

CH3
H

CH3
Br

ethyl acetate

succinonitrile

cyclopentanone


2-bromopropane

C4H8O2

C4H4N2

C5H8O2

C3H7Br

CH3O

CH2CH3
O

8

12

CH3 CH3
CH3 C

C

CH3CH2 I

16

Cl


Cl

CH3

CH3 CH3

December 2007

methyl propionate

2,2,3,3-tetramethylbutane

iodoethane

1,4-dichlorobutane

C4H8O2

C8H18

C2H5I

C4H8Cl2

2


Please Keep Absolutely
Confidential


17

Br

ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman
21

Br

Copyright: Copying or duplicating
these solutions in any form is
strictly prohibited

H2N

25

COOH

N

CH2C

29

CH2 C CH3
O


1,3-dibromopropane

4-aminobutyric acid

benzyl cyanide

benzyl methyl ketone

C3H6Br2

C4H9NO2

C8H7N

C9H10O

18

Br

22

Cl

26

OCH3

CH2NH2


30

O

1-bromo-3-chloropropane

anisole

benzylamine

propiophenone

C3H6BrCl

C7H8O

C7H9N

C9H10O

19

Br

N

C

23


27

CH2OH

OH

31

CH3
CH C H
O

4-bromobutyronitrile

benzyl alcohol

2-phenylethanol

2-phenylpropionaldehyde

C4H6NBr

C7H8O

C8H10O

C9H10O

28
+

NH3

20
CH3

December 2007

H

COO

24

OH

CH2Br

32

O

H
CH3

-

alanine

benzyl bromide


1-phenylethanol

butyrophenone

C3H7NO2

C7H7Br

C8H10O

C10H12O

3


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ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman
O

33

O
O

34

37


O

41

N

CH3

O

C

O

45

C

O

CH3

O

CH3

H CH3 O

O


H

t-butyl acetoacetate

dibenzylamine

propionic anhydride

1,1-diacetoxyethane

C8H14O3

C14H15N

C6H10O3

C6H10O4

CH3CH2 O C H

38

42

CH3

O

CH3


N

N

ethyl formate

CH3

O

35

O

39

C

H

O

COOCH3
CH3

diethyl oxalate

dimethyl methylmalonate


C6H10O4

C6H10O4

43

O

47

O
CH3

O

O

O

CH3
O

CH3

CH3

O

O


O

C

CH3OOC

O

N,N,N,N-tetramethyl-1,2ethanediamine
C6H16N2

C3H6O2

46

O

CH3

C
O

OCH3

benzil

2,5-hexanedione

ethylene glycol diacetate


methyl acetyllactate

C14H10O2

C6H10O2

C6H10O4

C6H10O4

36

40

44

O
CH3CH2O

OCH2CH3

48

O
CH3O

OCH3
O

December 2007


Copyright: Copying or duplicating
these solutions in any form is
strictly prohibited

O
O

C

C

O

O

1,2-diphenylethane

diethyl carbonate

dimethyl succinate

diethyl succinate

C14H14

C5H10O3

C6H10O4


C8H14O4

4


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Copyright: Copying or duplicating
these solutions in any form is
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ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman

O

49

53

O

O

57

CHCl2

O


H3C

CH3

H3C

CH3

61

OCH3
OCH3
OCH3

ethylene glycol dipropionate

α,α-dichlorotoluene

1,2,3-trimethoxybenzene

durene

C8H14O4

C7H6Cl2

C9H12O3

C10H14


CH3

50

51

O

O

C

C

O

54

58

OCH3
C

H
OCH3

CH3

62


CH3

CH3

CH3

CH3

butyric anhydride

benzaldehyde dimethylacetal

mesitylene

1,2,3,4-tetramethylbenzene

C8H14O3

C9H12O2

C9H12

C10H14

Br

55

Br


59

OH

63

CH3

COOH

CH3

CH3
CH3

CH3

CH3

52

CH3

CH3

1,4-dibromobenzene

benzilic acid


1,2,3-trimethylbenzene

1,2,3,5-tetramethylbenzene

C6H4Br2

C14H12O3

C9H12

C10H14

Br

Br

56

60

OH

CH3
CH3

OH

CH3

64


CH3

CH3

CH3

CH3

CH3

CH3

4,4'-dibromobiphenyl

catechol

1,2,4-trimethylbenzene

hexamethylbenzene

C12H8Br2

C6H6O2

C9H12

C12H18

December 2007


5


Please Keep Absolutely
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65

CH3

ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman
69

CH3
CH3

1,2,3,4,5,pentamethylcyclopentadiene
C10H16

66

CH3

CH3

3-hydroxybutanone
(acetoin)
C4H8O2


70

NH2

74

4-hydroxy-4-methyl-2pentanone
C6H12O2

C2H5NO

71

O
O

3,3-dimethylglutaric acid
C7H12O4

78

HOOC

COOH

O

hexylamine


2,2-dimethylpentanedioc
acid
C7H12O4

C6H15N

75

CH3

79

O
CH3CH2

O

CH3 CH3

CH3

O

CH3

Br

N

N

CH3
O

ethyl glycolate

isobutyl acetate

ethyl 2-bromopropionate

tetramethylurea

C4H8O3

C6H12O2

C5H9O2Br

C5H12N2O

68

72

O
CH3CH2O

December 2007

NH2


HOOC
COOH
CH3 CH3

O

acetamide

HO

CH3
CH3

2-methyl-2-butanol
(t-amyl alcohol)
C5H12O

HO

O

67

77

OH
CH3

O


CH3

H

73

OH
CH3

CH3

Copyright: Copying or duplicating
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C

N

76

COOH

OCH3
O

80

O


O

OCH3

ethyl cyanoacetate

3,3-dimethylbutyric acid

4,4-dimethoxy-2-butanone

1,3-dioxan

C5H7NO2

C6H12O2

C6H12O3

C4H8O2

6


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81

ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman

85

O

89

Br
OH

O

93

CH2

HO

O

H

O

1,4-dioxan

2-bromohexanoic acid

2-methylbut-3-en-2-ol

dibutyl ether


C4H8O2

C6H11O2Br

C5H10O

C8H18O

82

O

86

O

O

90

CN

H

+
-

C
H OH O


O

94

NH3

CH3

CN

O
O

83

Copyright: Copying or duplicating
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O

18-crown-6

2-ethylmalononitrile

threonine

butylbenzene


C12H24O6

C5H6N2

C4H9NO3

C10H14

H2C C

87

CH2Cl

91

CN

Br

95

C(CH3)3

Cl

2,3-dichloropropene

3-methylbutyronitrile


1-bromo-3-phenylpropane

t-butylbenzene

C3H4Cl2

C5H9N

C9H11Br

C10H14

84

88

O
Cl

O

H2N

C

C

92

H


NO2

96

CH3

4-chlorobutyl acetate

5-amino-1-pentyne

1-nitropropane

sec-butylbenzene

C6H11O2Cl

C5H9N

C3H7NO2

C10H14

December 2007

7


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ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman
101

97

Copyright: Copying or duplicating
these solutions in any form is
strictly prohibited

Cl

C(CH3)3

105

O
C

109

O
CH3O

C

CH3

HO


CH2OCH3

CH3

neopentylbenzene

p-chloroacetophenone

4-methoxyacetophenone

4-methoxymethylphenol

C11H16

C8H7OCl

C9H10O2

C8H10O2

98

CH2Cl

102
CH3

O


106

O

CH3

C

C

O

110
CH3

CH3
N C

N
CH3

Cl

4-(n-butyl)-α-chlorotoluene

p-toluyl chloride

p-cresyl acetate

4-dimethylaminobenzonitrile


C11H15Cl

C8H7OCl

C9H10O2

C9H10N2

99

103
O

CH3O

107

COOH

O
H3C

111

CH3
Br

C


N
CH3

OCH3

4-methyl-4-phenyl-2-pentanone
C12H16O

100

O
Br

C

104

p-anisic acid

methyl p-toluate

p-bromo-N,N-dimethylaniline

C8H8O3

C9H10O2

C8H10NBr

CH2O C


CH3

108

CH3O

CH2OH

O

CH3

112

O
CH3O

C
C(CH3)3

p-bromoacetophenone

benzyl acetate

p-methoxybenzyl alcohol

p-anisyl t-butyl ketone

C8H7OBr


C9H10O2

C8H10O2

C12H16O2

December 2007

8


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113

O
(H3C)3C

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ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman
117

121


O

O C CH3

CH3CH2O C

H

NH2

125

N

O

4-t-butylphenyl acetate

o-nitrobenzaldehyde

ethyl p-aminobenzoate

C12H16O2

C7H5NO3

C9H11NO2

(CH3)3C


C OCH3
O

118

H C

122

OCH3

CH3CH2O

C

O

NH2

p-ethoxybenzamide

C12H16O2

C8H8O2

C9H11NO2

NO2

119


p-ethoxyacetanilide
(phenacetin)
C10H13NO2
H

126
HO

N

C CH3
O

4-methoxybenzaldehyde

CH3O

O 2N

C

C

H

123

p-hydroxyacetanilide
(paracetamol)

C8H9NO2

127

O
CH3

CH3

O

O

methyl 4-t-butylbenzoate

115

C

CH3CH2O

NO2

114

H

O
C


NH C CH3

O

O

116

p-nitroanisole

4-nitrophenylacetylene

4-methylacetanilide

ethyl p-ethoxybenzoate

C7H7NO3

C8H5NO2

C8H9NO

C11H14O3

H C

NO2

120


124

O
C

O

O

C
H3C

OH

128

O
CH3 C

NH2

O

OCH3

O

p-nitrobenzaldehyde

4-acetoxybenzoic acid


4-aminoacetophenone

C7H5NO3

C9H8O4

C8H9NO

December 2007

CH3O

9

methyl (p-methoxyphenyl)propionionate
C11H14O3


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129

H

N

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ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman
133

137

O

O

O
C

O

O

O
C

141

H

O

O


CH3

C
O

N-isopropylbenzylamine

hydroquinone dipropionate

C10H15N

C12H14O4

130

134

OCH3
O

C

CH3

methyl 2-methoxy-2phenylacetate
C10H12O3

131

NCO


O

cyclopropyl methyl ketone
C5H8O

142
CH3O

C

O

O

138

O

O

1,3-dihydroxyphenyl
dipropionate
C12H14O4

C

C

H


OCH3

OH

C

O O

O

diethyl terephthalate

dimethyl o-phthalate

cyclopropane carboxylic acid

C12H14O4

C10H10O4

C4H6O2

O

135

C
C


139

O

O
O

143

H
C
O

O

132

phenyl isocyanate

diethyl o-phthalate

cycloheptanone

benzoylcylopropane

C7H5NO

C12H14O4

C7H12O


C10H10O

OCH3

136

O

OCH3
H

O

C

140

O
C

144

H

CH2
C

O


OCH2CH3

O

phenylacetaldehyde
dimethyl acetal
C10H14O2

December 2007

diethyl isophthalate

cycloheptatriene

ethyl cyclobutanecarboxylate

C12H14O4

C7H8

C7H12O2

10


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145


O

C(CH3)3

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ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman
149

153

157

CH3

(CH3)3C

O

OH

O

C
O

NEt2


(CH3)3C

4-t-butylcyclohexanone

benzyl benzoate

N,N-diethyl-m-toluamide

3,5-di-t-butylphenol

C10H18O

C14H12O2

C12H17NO

C14H22O

146

150

H

O

CH3

154


158

Br

Br

N
H3C

O

N-methylacetamide

H2N
NH2

Br

(p-cresyl)methyl phenyl
ketone
C15H14O2

C3H7NO

147

OH

O


CH3

151

CH3

O

2-bromophenol

3,5-dibromocumene

C6H5OBr

C9H10Br2

155

159

O

Br

O C CH3

O
COOH


148

1,4-diaminobutane

p-cresyl phenylacetate

C4H12N2

C15H14O2

H2N

NH2

152

Cl3C

COOH

acetylsalicylic acid
(aspirin)
C9H8O4

156

CCl3

160


NH2
Br

3-bromo-5-isopropylbenzoic
acid
C10H11O2Br

Br

O
O

H

O

1,5-diaminopentane
C5H14N2

December 2007

1,3-bis(trichloromethyl)benzene
C8H4Cl6

11

2,6-dibromoaniline

piperonal


C6H5NBr2

C8H6O3


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161

162

ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman
165

CH3
CH3

Copyright: Copying or duplicating
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169

O

NO2

173


O

3-nitro-o-xylene

2-cyclohexene-1-one

indane

α-tetralone

C8H9NO2

C6H8O

C9H10

C10H10O

Cl

CH3

Cl

Cl

166

170


O

174

O

OH
O

2,4,5-trichlorotoluene

2-hydroxycyclohex1-en-3-one
C6H8O2

C7H5Cl3

163

Cl

NH2

Cl

Cl

167

171


O
C CH3

3,3-dimethylindan-1-one

β-tetralone

C11H12O

C10H10O

175

O

H

164

2,4,5-trichloroaniline

1-acetyl-1-cylohexene

1-indanone

9-methylfluorene

C6H4NCl3


C8H12O

C9H8O

C14H12

CH3O
I

OCH3
I

168

172

CH3
CH3

O

4,6-diiodo-1,3dimethoxybenzene
C8H8O2I2

176

O
O

CH3


December 2007

CH3

4-methylpent-3-en-2-one
(mesityl oxide)
C6H10O

12

2-indanone

fluorenone

C9H8O

C13H8O


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177

CH3

ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman
181


CH3CH2

185

CH3

H

O
CH3
O

O

CH3

O

CH3
CH3

183

N

CH3
HO

C


C

C

mevalonic lactone
C6H10O3

December 2007

C C C CH2CH3
OH

H

187

C

C C

OH

CH3

COOH
H
CH3

3-methyl-1-phenylpent1-yn-3-ol

C12H14O

C C CH3

2-hydroxy-3-methylbutyric
acid
C5H10O3

191

OH

CH2

CH CH2

OH

OH OH

1-phenyl-1,3-pentadiyne

glycerol

C11H8

C3H8O3

COOCH3


188

H

C

O

C3H6Br2

CH3

CH3
C

O

CH3

2,5-dimethyl-3-hexyne2,5-diol
C8H14O2

184

OH

1,2-dibromopropane

190


CH3

CH3

CH3

CH3

O

2,2-dimethylglutaric
anhydride
C7H10O3
CH3

(Z)-1-methoxybut1-en-4-yne
C5H6O

1,2,2,6,6-pentamethylpiperidine
C10H21N

CH3

180

H

CH3

3,3-dimethylglutaric

anhydride
C7H10O3

O

CH2Br
H

186

O

O

O

182

O

CH3

CH3

C

4-ethyl-4-methyl-2,6piperidinedione
C8H13NO2

CH3


179

OCH3

Br

H

2,4,6-trimethyl1,3,5-trioxane
C6H12O3

CH3

N

189

H

C

O

178

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192

OH
CH3

O
H

C
HC

H

(Z)-3-methylpent-2en-4-ynal
C6H6O

C
NH2

CH

methyl 4-amino-3,5diethynylbenzoate
C12H9NO2

13

CH3
H

2-butanol

C4H10O


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193

ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman
197

O

Copyright: Copying or duplicating
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S

201

O
NH2

S

O

Cl


205

H

NH2
O

O

dibenzyl sulfoxide

p-aminobenzenesulfonamide
C6H8N2O2S

C14H14OS

vinyl 2-chloroethyl ether

cinnamaldehyde

C4H7OCl

C9H8O

198
194

202


O

S

206

O

S

N

O

COOH

CH2OH

CH3

O

(E)-3-(phenylthio)acrylic
acid
C9H8O2S

195

N-(p-tolyl)succinimide


cinnamyl alcohol

C4H6O2S

C11H11NO2

C9H10O

199

O
CH3

divinyl sulfone

S OCH2CH3

207

Cl

H

H

CH

C(CH3)3

O

H

ethyl p-toluenesulfonate

allyl p-anisyl thioether

C9H12O3S
O

phenylacetaldeyde
ethylene glycol acetal
C10H12O2

C10H12OS
O

CH3

O
CH2

CH3O

O

196

203

S


200

O

(E)-3-chloro-4,4-dimethyl-1phenyl-1-pentene
C13H17Cl

O
S

O

CH2CH2O
4

S CH3

204

S

CH(CH3)2

208

H
H

O


O

CH3

Br

CH3

p-tolyl methyl sulfoxide
C8H10OS

December 2007

tetraethylene glycol
ditosylate
C22H30O9S2

(E)-1-phenyl-4-methyl-1penten-3-one
C12H14O

14

(Z)-β-bromostyrene
C8H7Br


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209

ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman
213

H
NO2

Br

217

H
Cl

C

H

Cl

OH

O

214

Cl


Cl

Cl

3-benzyloxy-1-propanol

211

215

COOH

CH3O

O

219

Br

CH3O

222

H

CH3

5,6-dimethoxy-2coumaranone
C10H10O4


December 2007

Cl

OCH2CH3

2-chloroacetaldehyde
diethylacetal
C6H13O2Cl

223

H

OCH3

C

H

CH2 O CH2

methyl (E)-3-methylacrylate

1,3-dibenzylglycerol

C5H8O2

C17H20O3


220

CH3

O CH2

CH2
HO

OCH3
O

224

O
CH3O

OCH2CH3

CN

H

methyl 2,3-dibromo-3(p-nitrophenyl)propionate
C10H9NO4Br2

216

malonaldehyde dimethyl

acetal
C7H16O4

4-cyano-2,2dimethylbutyraldehyde
C7H11NO

O

C9H8O4

OCH2CH3

O

Br

212

218

COOH

COOH

homophthallic acid

OCH3 OCH3

diethyl isopropylidenemalonate
C10H16O4


O

O2N

OCH3

O

2,4,5-trichlorophenoxyacetic acid (2,4,5-T)
C8H5O3Cl3

C10H14O2

CH3O

OCH2CH3

CH3

1,1-di-(p-chlorophenyl)-2,2,2trichloroethane (DDT)
C14H9Cl5

C8H6BrNO2

221

O
CH3


CCl3

(E)-p-nitro-β-bromostyrene

210

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N
CN

OCH3

2,3-di-(p-anisyl)butyronitrile

2,5-dimethyl-2,4-hexadiene

pyridine

C18H19NO2

C8H14

C5H5N

15



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ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman
O

225

N

H3C

229

233

O

CH3

C

237

C


O2N

O

O

C
H

CH(CH3)2

N

C

CH(CH3)2

S
O

C
O

4-picoline

isopropyl nicotinate

citraconic anhydride


C6H7N

C9H11NO2

C5H4O3

226

CH3

230

N

227

234
CH3

N

238
COOH

O

NH2

H


CH3

N
N

2-picoline

2-methyl-6-aminopyridine

2-furoic acid

4-methylimidazole

C6H7N

C6H8N2

C5H4O3

C4H6N2

231

CH3

235

N
N


H3C

C(CH3)3

O

N

239
S

O

3-picoline

4-methylpyrimidine

2-furyl t-butyl ketone

benzothiophene

C6H7N

C5H6N2

C9H12O2

C8H6S

228


232

O
C

236

H
O

CH3

240

O2N
S

NO2

N

December 2007

2-(5-nitrothienyl) isopropyl
ketone
C8H9NO3S

N
H


3-acetylpyridine

styrene epoxide

2,4-dinitrothiophene

2,3,4,9-tetrahydrocarbazole

C7H7NO

C8H8O

C4H2N2O4S

C12H13N

16


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ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman
245

241
CH3


249

O

O

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O

N CH3

α-angelicalactone

octahydroanthracene

N-methylmorpholine

C5H6O2

C14H18

C5H11NO

253

OH
HO


N(CH3)2

N,N-dimethyl-2,3-dihydroxy1-propylamine
C5H13NO2

O
O

242

246

250

H
CH3

O

N
CH3

anthraquinone

cyclopentanone oxime

pseudoephedrine

C14H8O2


C5H9NO

C10H15NO

247

251

OH

255

N

H
O

N
C(CH3)3

H

butyrolactone

dodecahydrotriphenylene

cyclohexanone oxime

t-butylformamide


C4H6O2

C18H24

C6H11NO

C5H11NO

244

248

O
CH3

252

CH3

CH3
O

O

256

H
HS CH2 CH


N
H

CH3

tetramethyl-1,3cyclobutanedione
C8H12O2

December 2007

H

CH3

OH

O

O

254

O

2-methyltetrahydrofuran-3-one
C5H8O2

243

OH

N

N

COOH

C
O

triphenylene

ε-caprolactam

N-acetylcysteine

C18H12

C6H11NO

C5H9NO3S

17

CH3


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257


HO
HO

ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman
261

OH

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265

O
H

CH CH2NH CH3

269

OH
CH3

CH3

O
HO


H
OH

CH3

H

C

O
OH
CH3

N
H
O

adrenalin

3-methylbutyraldehyde

2-methyl-2,4-pentanediol

N-acetylglutamic acid

C9H13NO3

C5H10O


C6H14O2

C7H11NO5

258
N
H

CH2 CH COO+
NH3

262

266

OCH2CH3
CH2 CH

270

OCH3

H

O

CH
OH

OCH2CH3


HO

OCH2CH3
CH3

N
H
O

tryptophan

acrolein diethyl acetal

eugenol

N-acetyltyrosine ethyl ester

C11H12N2O2

C7H14O2

C10H12O2

C13H17NO4

259

263


H
N

S

O

C

C

H

271
O

C
(CH3)3C

O

HO C CH2CH2 CH COOH
O
NH2

C

C

CH3


N-acetylhomocysteine
thiolactone
C6H9NO2S

260

Cl

H

267

NH2

allylamine

E -1-chloro-4-(4-tbutylphenyl)but-1-en-3-yne
C14H15Cl

C3H7N

264

268

H

HO
O


OH
CH3

N

C4H6O

272

O

H

2,5-dihydrofuran

O

O

December 2007

glutamic acid

adamantine

N-acetylaspartic acid

2,3-dihydrofuran


C5H9NO4

C10H16

C6H9NO5

C4H6O

18


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273

COOH

ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman
277

281

Cl

O
O

N C


COOH

O CH2CH3

2,3-naphthalenedicarboxylic acid
C12H8O4

274

OCH3

2-chloronaphthalene

ethyl 4-piperidone-Ncarboxylate
C8H13NO3

C10H7Cl

278

282

COOH
CH3
N C
O
H

NO2


1-methoxy-4-nitronaphthalene
C11H9NO3
CH3

275

sec-butylbenzene

N-acetyl-2-amino-4-phenyl(E)-but-2-enoic acid
C12H13NO3

C10H14

279

283

CH3 O

CH3O

O

N
H

CH3

CH3


OCH3

1,5-dimethylnaphthalene

N-(1-methyl-1-phenylethyl)butyramide
C12H17NO

C12H12

276

280

CH3

O
OCH2CH3

CH3

1,3-dimethylnaphthalene
C12H12

December 2007

OCH2CH3
O

diethyl 2-(1,1dimethylheptyl)malonate

C16H30O4

19

OH

3-hydroxy-3-methyl-5,8dimethoxy-1-coumarinone
C13H16O4

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ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman

Chapter 9.2 – The Analysis of MixturesProblem 284

Problem 286

Problem 284
Compound

Mole %

ethanol


57

bromoethane

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Compound

Mole %

benzene

24

ethyl acetate

59

dioxane

17

Compound

Mole %

ethanol


41

bromoethane

59

43

Problem 285

Compound

Mole %

benzene

15

diethyl ether

dichoromethane

December 2007

Problem 287

46

39


20


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ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman

Problem 288

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Problem 290
Compound

Mole %

Compound

Mole %

benzene

13

fluorene


75

diethyl ether

22

fluorenone

25

dichoromethane

65

Compound

Mole %

4-nitroanisole

38

2-nitroanisole

62

Problem 291
Problem 289


December 2007

Compound

Mole %

benzene

23

ethyl acetate

51

dioxane

26

21


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ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman
Problem 294

Chapter 9.3 – Problems in 2D NMR
Problem 292

Proton
H1
H2
H3
H4

1-propanol

Chemical Shift (δ)
in ppm
3.49
1.50
0.85
2.95

Problem 293

December 2007

Carbon
C1
C2
C3

Chemical Shift (δ)
in ppm
64.0
25.5
9.9


1-iodobutane

22

isobutanol

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ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman

Problem 295

Problem 297
1

3-heptanone

CH3


2

3

4

5

CH2

C

CH2

CH2

6

CH2

4

7

1-bromobutane

CH3

3


CH3

2

CH2

1

CH2

CH2

Br

O

Proton

Chemical Shift (δ) in ppm

H1

0.91

H2

1.94

H4


1.97

H5

1.44

H6

1.14

H7

0.79

Proton

Carbon

H1

Chemical Shift (δ)
in ppm
3.39

C1

Chemical Shift (δ)
in ppm
33.4


H2

1.82

C2

34.7

H3

1.45

C3

21.4

H4

0.91

C4

13.2

Problem 298
1

3-octanone

2


CH3

CH2

5

δ-valerolactone

Proton

2

4

Chemical Shift
(δ) in ppm

Proton

O

Carbon
C1

Chemical Shift
(δ) in ppm
170.0

H2


2.08

C2

29.9

H3

1.16

C3

22.2

H4

1.08

C4

19.0

H5

3.71

C5

68.8


December 2007

5

CH2

CH2

6

CH2

7

CH2

8

CH3

Carbon

H1

Chemical Shift
(δ) in ppm
0.92

C1


Chemical Shift
(δ) in ppm
7.8

H2

1.92

C2

35.4

C3

209.0

1

O

C

4

O

3

Problem 296


3

23

H4

1.94

C4

42.1

H5

1.47

C5

23.7

H6

1.11

C6

31.7

H7


1.19

C7

22.7

H8

0.82

C8

14.0


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ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman

Problem 299

Problem 300
c

b

a


a

COOCH2CH3
d

diethyl diethylmalonate

e

f

g

CH3CH2 C

butyl ethyl ether

h

CH2

c

O

d

e


f

CH2 CH2 CH2 CH3

Ha

Chemical
Shift (δ)
in ppm
1.11

Hb

3.29

Cb

66.0

Hc

3.27

Cc

70.1

Ca

Chemical Shift

(δ)
in ppm
14.0

Hd

1.52

Cd

32.1

Cb

60.8

He

1.36

Ce

19.4

Cc

171.9

Hf


0.87

Cf

13.5

i

Carbon

Ha

Chemical Shift
(δ)
in ppm
1.19

Hb

4.13

Proton

j

k

Hd

0.76


Cd

8.1

He

1.88

Ce

24.5

Cf

58.0

Hg

1.88

Cg

24.5

Hh

0.76

Ch


8.1

Ci

171.9

Hj

4.13

Cj

60.8

Hk

1.19

Ck

14.0

December 2007

CH3

b

CH2CH3


COOCH2CH3

Proton

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24

Carbon

Ca

Chemical Shift
(δ)
in ppm
15.0


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ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman

Problem 301

Problem 302


1-iodobutane

butyl butyrate

Carbon

Ha

Chemical
Shift (δ)
in ppm
0.75

Ca

Chemical
Shift (δ)
in ppm
13.9

Hb

1.19

Cb

19.5

Hc


1.40

Cc

31.2

Hd

3.97

Cd

64.0

Ce

172.8

Proton

Hf

2.08

Cf

36.2

Hg


1.52

Cg

19.0

Hh

0.79

Ch

13.9

December 2007

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1-butanol

1-iodobutane

25

1

4


3

2

1

CH3

CH2

CH2

CH2

4

3

2

1

CH3

CH2

CH2

CH2 OH


I

1

1-butanol

H1

H Chemical
Shift (δ)
in ppm
2.70

H1

H Chemical
Shift (δ)
in ppm
3.41

H2

1.40

H2

1.27

H3


1.08

H3

1.39

H4

0.64

H4

0.84

-OH

1.95


×