5th edition Solutions Organic Structures from Spectra PDF

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Solutions for spectra textbook 5th edition...

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

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

Solutions Manual

Last updated: 14th January 2014

1

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1

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

9

BrCH2 CH2Br

13

Br

O

2

2-butanone

1,2-dibromoethane

cyclopentane

bromocyclopentane

C4H8O

C2H4Br2

C5H10

C5H9Br

CH3 CH2

OH

6

10

O CH3

O

CH 3 O

propionic acid

3

O CH3

4

CH2 CH3

7

O

C

C

CH3CH2 I

CH3

CH 3 CH3

1,2-butanedione (biacetyl) C4H6O2

C3H6O2

14

OH OH CH3

CH2C

N

CH2C

N

11

pinacol

iodoethane

C6H14O2

C2H5I

O

O

15

Cl2CH CH3

ethyl acetate

succinonitrile

1,4-cyclohexanedione

1,1-dichloroethane

C4H8O2

C4H4N2

C6H8O2

C2H4Cl2

CH2CH3

CH3O O

8

12

CH3 CH3 CH3

C

C

O

CH3

16

CH3 H

CH 3 OH

CH3 CH3

methyl propionate

2,2,3,3-tetramethylbutane

cyclopentanone

2-propanol

C4H8O2

C8H18

C5H8O2

C3H8O

Last updated: 14th January 2014

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17

CH3 H

21

CH3

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

25

N

C

CH2 OH

29

OH

Br

2-bromopropane

4-bromobutyronitrile

benzyl alcohol

C3H7Br

C4H6NBr

C7H8O

2-phenylethanol C8H10O

30 18

Cl

Cl

+ NH 3

22 CH3

19

H

26

COO

OH

CH2Br

H CH3

-

1,4-dichlorobutane

alanine

benzyl bromide

1-phenylethanol

C4H8Cl2

C3H7NO2

C7H7Br

C8H10O

Br

Br

23

H2N

27

COOH

CH2C

N

31

CH2 C CH 3 O

20

1,3-dibromopropane

4-aminobutyric acid

benzyl cyanide

benzyl methyl ketone

C3H6Br2

C4H9NO2

C8H7N

C9H10O

Br

Cl

24

28

OCH3

CH2NH2

32

O

1-bromo-3-chloropropane

anisole

benzylamine

propiophenone

C3H6BrCl

C7H8O

C7H9N

C9H10O

Last updated: 14th January 2014

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33

37

CH3 CH C

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ORGANIC STRUCTURES FROM SPECTRA – 5th EDITION L D Field, S Sternhell and J R Kalman 41

O

O

45

O CH3

H

O

O

CH3

O

O

O

O

2-phenylpropionaldehyde

benzil

2,5-hexanedione

ethylene glycol diacetate

C9H10O

C14H10O2

C6H10O2

C6H10O4

34

38

O

42

46

O CH3CH2O

O CH3O

OCH2CH3

OCH3 O

butyrophenone

1,2-diphenylethane

C10H12O

C14H14

diethyl carbonate

dimethyl succinate

C5H10O3

C6H10O4

O

35

O O

36

39

O

43

N

CH3

O

C

47

C

O

O

CH3 O

H

O

CH 3

H CH 3 O

t-butyl acetoacetate

dibenzylamine

propionic anhydride

1,1-diacetoxyethane

C8H14O3

C14H15N

C6H10O3

C6H10O4

CH3 CH2 O C H

40

44

CH3

O

N CH3

N

CH 3

C3H6O2

Last updated: 14th January 2014

C

C

O

CH3OOC H

COOCH3 CH3

O

CH 3

ethyl formate

48

O O

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

4

diethyl oxalate

dimethyl methylmalonate

C6H10O4

C6H10O4

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

CH 3

49

O O

CH3

53

CH3 C O

Br

OCH3

57

Br

61

OH COOH

CH3 CH3

methyl acetyllactate

1,4-dibromobenzene

benzilic acid

mesitylene

C6H10O4

C6H4Br2

C14H12O3

C9H12

50

54

O O

C

C

Br

58

Br

62

OH

O

CH3 CH3

OH

O

CH 3

diethyl succinate

4,4'-dibromobiphenyl

catechol

1,2,3-trimethylbenzene

C8H14O4

C12H8Br2

C6H6O2

C9H12

O

51

55

O

O

59

CHCl2

63

OCH3

O

CH 3 CH3

OCH 3

CH 3

OCH3

ethylene glycol dipropionate

,-dichlorotoluene

1,2,3-trimethoxybenzene

1,2,4-trimethylbenzene

C8H14O4

C7H6Cl2

C9H12O3

C9H12

H

52

O C

O O

C

56

C

60

OCH3 C

64

C

H3C

CH3

H3C

CH3

H OCH3 H

C

C

C

C

H

butyric anhydride

benzaldehyde dimethylacetal

1,3,5-triethynylbenzene

durene

C8H14O3

C9H12O2

C12H6

C10H14

Last updated: 14th January 2014

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65

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

CH 3

CH3

CH 3

69

CH3

73

NH2

77

OH CH3

O

OH CH3

CH3 O

1,2,3,4-tetramethylbenzene

acetamide

C10H14

C2H5NO

66

CH 3

70

74

O HO

CH3

3-hydroxybutanone (acetoin) C4H8O2

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

78

HO

NH2

O

O

CH3

CH3 CH3

CH 3

67

1,2,3,5-tetramethylbenzene

ethyl glycolate

C10H14

C4H8O3

CH3

CH 3

CH3

68

71

75 O

CH 3

CH3

4-hydroxy-4-methyl-2pentanone C6H12O2

O

CH3

hexylamine C6H15N

79

O CH3CH2

O

CH3

O Br

CH 3

hexamethylbenzene

methyl vinyl ketone

isobutyl acetate

ethyl 2-bromopropionate

C12H18

C4H6O

C6H12O2

C5H9O2Br

CH 3 CH3 H

CH 3 CH3 CH 3

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

Last updated: 14th January 2014

72

76

O CH3CH2O

C

N

COOH

80

OCH 3 O

OCH 3

ethyl cyanoacetate

3,3-dimethylbutyric acid

4,4-dimethoxy-2-butanone

C5H7NO2

C6H12O2

C6H12O3

6

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81

HOOC COOH CH 3 CH 3

85

89

O

93

Br OH

O

82

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

H

O

3,3-dimethylglutaric acid

1,4-dioxane

2-bromohexanoic acid

2-methylbut-3-en-2-ol

C7H12O4

C4H8O2

C6H11O2Br

C5H10O

HOOC

COOH

86

O

O

O

O

O

2,2-dimethylglutaric acid C7H12O4

83

CH3 CH3 CH3

N

87

94

CN

H

18-crown-6

2-ethylmalononitrile

3-methylbutyraldehyde

C12H24O6

C5H6N2

C5H10O

91

CH2Cl

95

CN

H

NH3+

CH3

C H OH O

Cl

CH3

O

CN

O

H2 C C

N

90

O

84

CH2

HO

tetramethylurea

2,3-dichloropropene

3-methylbutyronitrile

threonine

C5H12N2O

C3H4Cl2

C5H9N

C4H9NO3

O

O

88

92

O Cl

O

H 2N

C

C

H

96

O

-

Br

CH3

1,3-dioxane

4-chlorobutyl acetate

5-amino-1-pentyne

1-bromo-3-phenylpropane

C4H8O2

C6H11O2Cl

C5H9N

C9H11Br

Last updated: 14th January 2014

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97

NO2

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ORGANIC STRUCTURES FROM SPECTRA – 5th EDITION L D Field, S Sternhell and J R Kalman 101

105

109 O

1-nitropropane C3H7NO2

CH3O

COOH

sec-butylbenzene

4-methyl-4-phenyl-2pentanone

p-anisic acid

C10H14

C12H16O

C8H8O3

102 98

106

O

110

O Br

CH2O

C

C

dibutyl ether

cymene

p-bromoacetophenone

benzyl acetate

C8H18O

C10H14

C8H7OBr

C9H10O2

99

103

107

111

O Cl

C(CH 3)3

O CH3O

C

C CH3

CH3

100

CH3

O

CH3

butylbenzene

neopentylbenzene

p-chloroacetophenone

4-methoxyacetophenone

C10H14

C11H16

C8H7OCl

C9H10O2

C(CH3 )3

104

108

CH2 Cl

O CH3

112

O CH3

C

O

C

Cl

t-butylbenzene

4-(n-butyl)--chlorotoluene

p-toluoyl chloride

p-cresyl acetate

C10H14

C11H15Cl

C8H7OCl

C9H10O2

Last updated: 14th January 2014

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CH 3

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113

117

O H3C

121

CH3 Br

C

N

CH3O

NO2

125

O 2N

C

methyl p-toluate

p-bromo-N,N-dimethylaniline

p-nitroanisole

4-nitrophenylacetylene

C9H10O2

C8H10NBr

C7H7NO3

C8H5NO2

CH3O

CH 2OH

118

122

O CH3O

C

H

C

NO2

126

O C

O

O

C(CH3)3

C

OH

O

H3C

115

H

C

CH3

OCH3

114

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

p-methoxybenzyl alcohol

p-anisyl t-butyl ketone

p-nitrobenzaldehyde

4-acetoxybenzoic acid

C8H10O2

C12H16O2

C7H5NO3

C9H8O4

HO

CH2 OCH3

119

123

O (H3C)3C

127

O

O C CH 3

CH3CH2 O

H

C

NH2

O

NO2

4-methoxymethylphenol

4-t-butylphenyl acetate

o-nitrobenzaldehyde

ethyl p-aminobenzoate

C8H10O2

C12H16O2

C7H5NO3

C9H11NO2

116

CH3 N C

N

120

(CH3 )3C

C OCH3 O

CH3

124

H C

OCH3

128

CH3CH2O

O

C

NH2

O

4-dimethylaminobenzonitrile

methyl 4-t-butylbenzoate

p-anisaldehyde

p-ethoxybenzamide

C9H10N2

C12H16O2

C8H8O2

C9H11NO2

Last updated: 14th January 2014

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129

133

O CH3 C

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ORGANIC STRUCTURES FROM SPECTRA – 5th EDITION L D Field, S Sternhell and J R Kalman 137

O C

NH 2

O

141

NCO

C

O

C

O

O O

O

4-aminoacetophenone

ethyl p-ethoxybenzoate

phenyl isocyanate

diethyl o-phthalate

C8H9NO

C11H14O3

C7H5NO

C12H14O4

130

134

O CH 3

NH C CH 3

138 CH3O

4-methylacetanilide

O

142

OCH3

OCH3

O

H

methyl (p-methoxyphenyl)propionate C11H14O3

C9H11NO

OCH3

phenylacetaldehyde dimethyl acetal C10H14O2

O

O

C

C

O

diethyl isophthalate C12H14O4

139 131

135

H N

C

H N

C CH3 O

O

O

143

O C

O

O

C

O

O O

p-ethoxyacetanilide (phenacetin) C10H13NO2

HO

H

O

CH3CH2O

132

N

CH3

136

N-isopropylbenzylamine

hydroquinone dipropionate

C10H15N

C12H14O4

OCH3 O

140 CH3

O

O C

144

C

O

O

1,3-dihydroxyphenyl dipropionate C12H14O4

O

CH3O

C

C

OCH3

O O

p-hydroxyacetanilide (paracetamol) C8H9NO2

Last updated: 14th January 2014

methyl 2-methoxy-2phenylacetate C10H12O3

10

diethyl terephthalate

dimethyl o-phthalate

C12H14O4

C10H10O4

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145

O

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ORGANIC STRUCTURES FROM SPECTRA – 5th EDITION L D Field, S Sternhell and J R Kalman 149

153

H

H2N

NH2

157

CH3

C

O O

O

cycloheptanone

cyclopropyl phenyl ketone

1,5-diaminopentane

C7H12O

C10H10O

C5H14N2

146

150

154

H

CH 2

158

OCH2CH3

C

(p-cresyl)methyl phenyl ketone C15H14O2

F3C

CH3

O

CH2 OH

O

O

147

cycloheptatriene

ethyl cyclobutane-carboxylate

2,2,2-trifluoroethanol

p-cresyl phenylacetate

C7H8

C7H12O2

C2H3F3O

C15H14O2