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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
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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
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17
Br
ORGANIC STRUCTURES FROM SPECTRA – 4th EDITION
L D Field, S Sternhell and J R Kalman
21
Br
Copyright: Copying or duplicating
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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
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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
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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
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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
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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
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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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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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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