Organic Structures from Spectra: Solutions Manual

39 Pages·2007·0.444 MB·English

by  Leslie D. Field, Sev Sternhell, John R. Kalman

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L D Field, S Sternhell and J R Kalman

Solutions Manual

December 2007 1
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1 5 BrCH CH Br 9 OH OH 13 ClCH CH
2 2 2 3
O
CH C C CH
3 3
CH3 CH3
2-butanone 1,2-dibromoethane pinacol 1,1-dichloroethane

C H O C H Br C H O C H Cl
4 8 2 4 2 6 14 2 2 4 2

2 CH CH OH 6 O 10 14 CH CH
3 2 O O 3 3
O CH3 CH3 H OH
O

propionic acid 1,2-butanedione 1,4-cyclohexanedione 2-propanol
(biacetyl)
C H O C H O C H O C H O
3 6 2 4 6 2 6 8 2 3 8

3 O 7 CHC N 11 15 CH CH
2 O 3 3
CH CH
2 3
CH3 O CH2C N H Br
ethyl acetate succinonitrile cyclopentanone 2-bromopropane

C H O C H N C H O C H Br
4 8 2 4 4 2 5 8 2 3 7

4 CHO CHCH 8 CH CH 12 CHCH I 16 Cl
3 2 3 3 3 3 2 Cl

O CH3 C C CH3
CH CH
3 3
methyl propionate 2,2,3,3-tetramethylbutane iodoethane 1,4-dichlorobutane

C H O C H C H I C H Cl
4 8 2 8 18 2 5 4 8 2

December 2007 2
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17 Br Br 21 H2N COOH 25 CHC N 29 CH C CH
2 2 3

O

1,3-dibromopropane 4-aminobutyric acid benzyl cyanide benzyl methyl ketone

C H Br C H NO C H N C H O
3 6 2 4 9 2 8 7 9 10

18 Br Cl 22 26 30 O
OCH CHNH
3 2 2

1-bromo-3-chloropropane anisole benzylamine propiophenone

C H BrCl C H O C H N C H O
3 6 7 8 7 9 9 10

19 Br C N 23 27 OH 31 CH
CHOH 3
2
CH C H

O

4-bromobutyronitrile benzyl alcohol 2-phenylethanol 2-phenylpropionaldehyde

C H NBr C H O C H O C H O
4 6 7 8 8 10 9 10
28
20 + 24 OH 32 O
NH3 CH2Br H
CH3 H COO- CH3

alanine benzyl bromide 1-phenylethanol butyrophenone

C H NO C H Br C H O C H O
3 7 2 7 7 8 10 10 12

December 2007 3
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O O
33 O O 37 N 41 C C 45 CH3 O O CH3
O
O CH3 H O H CH3 O
t-butyl acetoacetate dibenzylamine propionic anhydride 1,1-diacetoxyethane

C H O C H N C H O C H O
8 14 3 14 15 6 10 3 6 10 4

34 CH CH O C H 38 CH 42 O 46 CHOOC COOCH
3 2 3 3 3
O CH N N CH3 O C C O H CH3
3
CH3 O
ethyl formate N,N,N,N-tetramethyl-1,2- diethyl oxalate dimethyl methylmalonate
ethanediamine
C H O C H N C H O C H O
3 6 2 6 16 2 6 10 4 6 10 4

35 O 39 O 43 O 47 O CH3
CH O OCH
3 O CH CH O C 3
3 3
O O O O

benzil 2,5-hexanedione ethylene glycol diacetate methyl acetyllactate

C H O C H O C H O C H O
14 10 2 6 10 2 6 10 4 6 10 4

36 40 O 44 O 48 O
CH3CH2O OCH2CH3 CH3O OCH3 O C C O
O
O

1,2-diphenylethane diethyl carbonate dimethyl succinate diethyl succinate

C H C H O C H O C H O
14 14 5 10 3 6 10 4 8 14 4

December 2007 4
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O HC CH
3 3
49 O 53 57 OCH 61
O CHCl 3
2 HC CH
O OCH3 3 3
OCH
3
ethylene glycol dipropionate α,α-dichlorotoluene 1,2,3-trimethoxybenzene durene

C H O C H Cl C H O C H
8 14 4 7 6 2 9 12 3 10 14
CH3 CH3 CH3
50 O O 54 OCH3 58 62
CH CH CH
C C C H 3 3 3
O
OCH CH
3 3
butyric anhydride benzaldehyde dimethylacetal mesitylene 1,2,3,4-tetramethylbenzene

C H O C H O C H C H
8 14 3 9 12 2 9 12 10 14

51 55 59 CH 63 CH
OH 3 3
Br Br
COOH CH CH CH
3 3 3
CH CH
3 3

1,4-dibromobenzene benzilic acid 1,2,3-trimethylbenzene 1,2,3,5-tetramethylbenzene

C H Br C H O C H C H
6 4 2 14 12 3 9 12 10 14

52 56 OH 60 CH3 64 CH3 CH3
Br Br
CH CH CH CH
OH 3 3 3 3

CH CH
3 3
4,4'-dibromobiphenyl catechol 1,2,4-trimethylbenzene hexamethylbenzene

C H Br C H O C H C H
12 8 2 6 6 2 9 12 12 18

December 2007 5
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65 CH3 CH3 69 OH 73 OH 77 HOOC COOH
CH3 CH CH3 CH CH3 CH3
CH3 CH3 O 3 CH 3
H CH3 3
1,2,3,4,5,- 3-hydroxybutanone 2-methyl-2-butanol 3,3-dimethylglutaric acid
pentamethylcyclopentadiene (acetoin) (t-amyl alcohol)
C H C H O C H O C H O
10 16 4 8 2 5 12 7 12 4

66 CH3 NH2 70 HO 74 NH2 78 HOOC COOH
O O

acetamide 4-hydroxy-4-methyl-2- hexylamine 2,2-dimethylpentanedioc
pentanone acid
C H NO C H O C H N C H O
2 5 6 12 2 6 15 7 12 4

67 O 71 75 O 79 CH CH
3 3
O CH
HO O 3 CH3CH2 O CH3 N N
O Br CH3 CH3
O

ethyl glycolate isobutyl acetate ethyl 2-bromopropionate tetramethylurea

C H O C H O C H O Br C H N O
4 8 3 6 12 2 5 9 2 5 12 2

68 O 72 COOH 76 OCH3 80 O O
C N
CH3CH2O O OCH3
ethyl cyanoacetate 3,3-dimethylbutyric acid 4,4-dimethoxy-2-butanone 1,3-dioxan

C H NO C H O C H O C H O
5 7 2 6 12 2 6 12 3 4 8 2

December 2007 6
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81 O 85 Br 89 93 O
CH
OH HO 2
O O H

1,4-dioxan 2-bromohexanoic acid 2-methylbut-3-en-2-ol dibutyl ether

C H O C H O Br C H O C H O
4 8 2 6 11 2 5 10 8 18

82 O O 86 CN 90 H NH3+ 94
O O CN CH3 C O-
H OH O
O O

18-crown-6 2-ethylmalononitrile threonine butylbenzene

C H O C H N C H NO C H
12 24 6 5 6 2 4 9 3 10 14

83 CHCl 87 91 95
H2C C 2 CN Br C(CH3)3
Cl
2,3-dichloropropene 3-methylbutyronitrile 1-bromo-3-phenylpropane t-butylbenzene

C H Cl C H N C H Br C H
3 4 2 5 9 9 11 10 14

84 O 88 H2N C C H 92 NO2 96
Cl
O CH
3
4-chlorobutyl acetate 5-amino-1-pentyne 1-nitropropane sec-butylbenzene

C H O Cl C H N C H NO C H
6 11 2 5 9 3 7 2 10 14

December 2007 7
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97 101 O 105 O 109
HO CH OCH
2 3
C(CH3)3 Cl C CH3O C
CH CH
3 3
neopentylbenzene p-chloroacetophenone 4-methoxyacetophenone 4-methoxymethylphenol

C H C H OCl C H O C H O
11 16 8 7 9 10 2 8 10 2

98 102 O 106 O 110 CH
3
CHCl
2 CH3 C CH3 O C CH3 N C N
Cl CH
3
4-(n-butyl)-α-chlorotoluene p-toluyl chloride p-cresyl acetate 4-dimethylaminobenzonitrile

C H Cl C H OCl C H O C H N
11 15 8 7 9 10 2 9 10 2

99 103 107 O 111 CH
3
O CH3O COOH
HC C Br N
3
OCH CH
3 3
4-methyl-4-phenyl-2-pentanone p-anisic acid methyl p-toluate p-bromo-N,N-dimethylaniline
C H O
12 16
C H O C H O C H NBr
8 8 3 9 10 2 8 10

100 O 104 108 112 O
Br C CH2O C CH3 CH3O CH2OH CHO C
3
O
CH C(CH)
3 33
p-bromoacetophenone benzyl acetate p-methoxybenzyl alcohol p-anisyl t-butyl ketone

C H OBr C H O C H O C H O
8 7 9 10 2 8 10 2 12 16 2

December 2007 8
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113 O 117 O 121 125 H
CHCHO C NH
(H3C)3C O C CH3 H 3 2 O 2 N C CH3

O
NO CHCHO
2 3 2
4-t-butylphenyl acetate o-nitrobenzaldehyde ethyl p-aminobenzoate p-ethoxyacetanilide
(phenacetin)
C H O C H NO C H NO C H NO
12 16 2 7 5 3 9 11 2 10 13 2

H
114 118 122 126
(CH3)3C C OCH3 H C OCH3 CH3CH2O C NH2 HO N C CH3
O O O O
methyl 4-t-butylbenzoate 4-methoxybenzaldehyde p-ethoxybenzamide p-hydroxyacetanilide
(paracetamol)
C H O C H O C H NO C H NO
12 16 2 8 8 2 9 11 2 8 9 2

115 119 123 O 127 O
CH3O NO2 O2N C C H
CH3 NH C CH3 C O

O

p-nitroanisole 4-nitrophenylacetylene 4-methylacetanilide ethyl p-ethoxybenzoate

C H NO C H NO C H NO C H O
7 7 3 8 5 2 8 9 11 14 3

116 120 O 124 O 128
H C NO
2
O O C OH CH3 C NH2 CH3O O OCH3
C
HC O
3
p-nitrobenzaldehyde 4-acetoxybenzoic acid 4-aminoacetophenone methyl (p-methoxyphenyl)-
propionionate
C H NO C H O C H NO C H O
7 5 3 9 8 4 8 9 11 14 3

December 2007 9
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129 H 133 O 137 O O O O 141 H
N O C C
CH
3
O C
O

O

N-isopropylbenzylamine hydroquinone dipropionate 1,3-dihydroxyphenyl cyclopropyl methyl ketone
dipropionate
C H N C H O C H O C H O
10 15 12 14 4 12 14 4 5 8

130 OCH3 134 O O 138 142 H
O CH C C CH3O C C OCH3 C OH
3 O O
O O O
O

methyl 2-methoxy-2- diethyl terephthalate dimethyl o-phthalate cyclopropane carboxylic acid
phenylacetate
C H O C H O C H O C H O
10 12 3 12 14 4 10 10 4 4 6 2

O
131 135 139 143 H
NCO C O
O C
O
C
O

O
phenyl isocyanate diethyl o-phthalate cycloheptanone benzoylcylopropane

C H NO C H O C H O C H O
7 5 12 14 4 7 12 10 10

132 OCH3 136 O O 140 144 H
OCH3 C C CH2 OCH2CH3
H O O C
O

phenylacetaldehyde diethyl isophthalate cycloheptatriene ethyl cyclobutanecarboxylate
dimethyl acetal
C H O C H O C H C H O
10 14 2 12 14 4 7 8 7 12 2

December 2007 10