Tables of Unknowns and Derivatives - Macmillan Learning

APPENDIX

Tables of Unknowns and Derivatives

The following tables list several hundred organic compounds and provide representative examples of the six functional-group classes that are treated in Part 4, Organic Qualitative Analysis. The functional groups appear in alphabetical order in Tables 1?7. In each table, compounds are listed in order of increasing boiling points; solids appear last in each table in order of increasing melting points. Compounds are arbitrarily listed by increasing boiling points unless their melting points are above 40?C. Many pure compounds that melt just above room temperature may be in the liquid state when you encounter them due to depression of their melting points by impurities. Remember also that the melting points we list may be 2??3?C higher or even more than the values you measure, because the listed melting points are those of the purified compounds.

When a derivative has been reported to decompose on melting, a "d" marks the melting point. When no solid derivative is listed in standard reference tables for an alcohol, aldehyde, ketone, amine, carboxylic acid, or phenol, a dash appears in the table in place of the derivative's melting point. In a few cases, two widely different melting points for a compound are listed in the literature; we include both, the second one in parentheses. The derivatives of multifunctional compounds that can form through derivatization at more than one site are shown by the notation "(mono)," "(di)," or "(tri)" after the melting point.

357

To accompany Techniques in Organic Chemistry, Second Edition, by Jerry R. Mohrig, Christina Noring Hammond, and Paul F. Schatz. ? 2006 by W. H. Freeman and Comapny. All rights reserved.

358

Part 4 ? Organic Qualitative Analysis

T A B L E 1 Alcohols

Compound

bp, ?C

Methanol Ethanol 2-Propanol 2-Methyl-2-propanol 2-Propen-1-ol 1-Propanol 2-Butanol 2-Methyl-2-butanol 2-Methyl-1-propanol 1-Butanol 3-Pentanol 2-Pentanol 3-Methyl-3-pentanol 2-Methoxyethanol 1-Chloro-2-propanol 2-Methyl-1-butanol 3-Methyl-1-butanol 2-Chloroethanol 4-Methyl-2-pentanol 2-Ethoxyethanol 3-Hexanol 1-Pentanol 2-Hexanol Cyclopentanol 3-Hydroxy-2-butanone 2,2,2-Trichloroethanol 1-Hexanol 2-Heptanol Cyclohexanol 1-Amino-2-propanol 4-Hydroxy-4-methyl-

2-pentanone 2-Furylmethanol 1-Heptanol 2-Octanol 1,2-Propanediol 1-Octanol 1,2-Ethanediol 1-Phenylethanol Benzyl alcohol 1,3-Propanediol 2-Phenylethanol 1-Decanol 3-Phenyl-1-propanol Cinnamyl alcohol 1-Dodecanol

(lauryl alcohol) 4-Methoxybenzyl

alcohol Glycerol ()-Menthol

65 78 83 83 97 97 99 102 108 116 116 119 123 124 127 129 131 131 132 135 135 138 139 140 145 151 157 159 161 163

166 171 176 179 187 194 197 202 205 214 219 231 236 257

259

259 290d

mp, ?C

25

19 25

20 33 24 24 43

3,5-Dinitrobenzoate

107 93

122 142

49 74 75 116 86 64 99 61 96 (62) ---- 77 70 61 95 65 75 97 (77) 46 38 115 ---- 142 58 49 112 ----

55 80 47 32 ---- 61 169 (di) 93 112 178 (di) 108 57 92 121

60

---- ---- 153

1-Naphthylurethane

124 79

106 101 108

80 97 72 104 71 95 74 83 112 ---- 82 68 101 88 67 ---- 68 60 118 ---- 120 60 54 129 ----

---- 130

62 63 153 (di) 67 176 (di) 106 134 164 (di) 119 73 ---- 114

80

---- 191 (tri) 119

Phenylurethane

47 52 76 136 70 57 65 42 86 61 48 ---- 43 ---- ---- 31 55 51 143 ---- ---- 46 ---- 132 ---- 87 42 ---- 82 ----

---- 45 60

114 ----

74 157 (di)

92 77 137 (di) 78 59 45 90

74

92 180 (tri) 111

To accompany Techniques in Organic Chemistry, Second Edition, by Jerry R. Mohrig, Christina Noring Hammond, and Paul F. Schatz. ? 2006 by W. H. Freeman and Comapny. All rights reserved.

Appendix ? Tables of Unknowns and Derivatives

359

T A B L E 1 Alcohols (continued)

Compound

bp, ?C

mp, ?C

2,2-Dimethyl-1-

propanol

113

53

Diphenylmethanol

(benzhydrol)

288

69

Benzoin

133 (137)

()-Cholesterol

148

()-Borneol

208

3,5-Dinitrobenzoate

----

141 ---- ---- 154

1-Naphthylurethane

100

135 140 176 132

Phenylurethane

144

139 165 168 138

T A B L E 2 Aldehydes

Compound

Propanal 2-Butenal (trans) Hexanal Heptanal 2-Furancarboxaldehyde Cyclohexane-

carboxaldehyde Octanal Benzaldehyde Phenylethanal 2-Hydroxy-

benzaldehyde 4-Methylbenzaldehyde 2-Chlorobenzaldehyde 3-Phenylpropanal 3-Bromobenzaldehyde 2-Methoxybenzaldehyde 4-Methoxybenzaldehyde Cinnamaldehyde (trans) 3,4-Methylenedioxy-

benzaldehyde 3,4-Dimethoxy-

benzaldehyde 4-Chlorobenzaldehyde 4-Bromobenzaldehyde 3-Nitrobenzaldehyde 4-Hydroxy-3-methoxy-

benzaldehyde (Vanillin) 3-Hydroxybenzaldehyde 4-Hydroxybenzaldehyde

bp, ?C

49 103 128 155 161

161 171 179 194

196 204 213 224 235 245 247 252

263

214

mp, ?C

34

38

37 44 47 56 58 80 104 115

2,4-Dinitrophenylhydrazone

150 190 104 108 229 (212)

172 106 237 121

248 232 212 149 ---- 253 254 255d

266d

262 254 257 293d

271d 257d 280d

Semicarbazone

89 (154) 199 106 109 202

173 98

222 153

231 234 (215) 225 (146) 127 205 215d 210 215

230

177 230 228 246

229 198 224

To accompany Techniques in Organic Chemistry, Second Edition, by Jerry R. Mohrig, Christina Noring Hammond, and Paul F. Schatz. ? 2006 by W. H. Freeman and Comapny. All rights reserved.

360

Part 4 ? Organic Qualitative Analysis

T A B L E 3 Amines

Compound

Classa bp, ?C mp, ?C Benzamideb Benzenesulfonamideb

Picrateb

tert-Butylamine

1?

46

Propylamine

1?

49

Diethylamine

2?

55

Allylamine

1?

58

sec-Butylamine

1?

63

2-Amino-2-methylbutane 1?

77

Butylamine

1?

77

Diisopropylamine

2?

83

Pyrrolidine

2?

89

Triethylamine

3?

89

1-Aminopentane

1?

104

Piperidine

2?

105

Dipropylamine

2?

110

Ethylenediamine

1?

116

1-Aminohexane

1?

129

Morpholine

2?

130

Diisobutylamine

2?

138

2-Aminoheptane

1?

143

1-Aminoheptane

1?

155

Tripropylamine

3?

156

Dibutylamine

2?

160

1-Amino-2-propanol

1?

163

Indole-3-acetic acid

2?

168

2-Fluoroaniline

1?

176

N,N-Dimethylbenzylamine 3?

182

N-Methylbenzylamine

2?

182

Benzylamine

1?

184

4-Fluoroaniline

1?

186

1-Phenylethylamine

1?

187

2-Phenylethylamine

1?

198

Tributylamine

3?

216

4-Aminomethylpyridine

1? (3?) 230

Aminodiphenylmethane 1?

295

2-Amino-6-methylpyridine 1? (3?) 208

41

2-Benzoylpyridine

3?

42

4-Methylaniline

1?

200

45

2-Aminobiphenyl

1?

49

6-Amino-1-hexanol

1?

57

Methoxyaniline

1?

58

4-Bromoaniline

1?

245d 66

4-Iodoaniline

1?

67

2-Nitroaniline

1?

71

4-Chloroaniline

1?

72

Tribenzylamine

3?

91

3-Nitroaniline

1?

113

2,4,6-Tribromoaniline

1?

119

3-Aminophenol

1?

122

3-(Dimethylaminomethyl)-

indole

3?

133

2-Aminobenzoic acid

1?

146

4-Nitroaniline

1?

147

134 84 42

---- 76

---- 42

---- ---- ---- ----

48 ---- 244 (di)

40 75 ---- ---- ---- ---- ---- ---- ---- 113 ---- ---- 105 185 120 116 ---- ---- ---- 90 ---- 158 102 ---- 154 204 222 110 192 ---- 155 198 174 (198)

---- 182 199

---- 36 42 39 70

---- ---- ---- ---- ---- ----

93 51 168 (di) 96 118 55 ---- ---- ---- ---- ---- ---- ---- ---- ---- 88 ---- ---- 69 ---- ---- ---- ---- ---- 120 ---- ---- 95 134 ---- 104 122 ---- 136 ---- ----

---- ---- 139

198 135 155 140 139 183 151 140 112 (163) 173 139 152

75 233 (di) 126 146 121 ---- 121 116

59 142 ---- ----

93 117 194 ---- ---- 174 106 ---- ---- 202 130 182 ---- ---- ---- 180 ----

73 ---- 190 143 ---- ----

---- 104 100

To accompany Techniques in Organic Chemistry, Second Edition, by Jerry R. Mohrig, Christina Noring Hammond, and Paul F. Schatz. ? 2006 by W. H. Freeman and Comapny. All rights reserved.

Appendix ? Tables of Unknowns and Derivatives

361

TABLE 3 Compound

Amines (continued)

Classa

bp, ?C mp, ?C Benzamideb Benzenesulfonamideb

Picrateb

3-Aminobenzoic acid

1?

2-Aminophenol

1?

4-Aminophenol

1?

4-Aminobenzoic acid

1?

-Alanine

1?

Glycine

1?

173 174 184 189 200d 230d

248 ---- 234 (di) 278 120 188

---- 141 125 ---- ---- ----

---- ---- ---- ---- ---- 202

a. 1?, primary; 2?, secondary; 3?, tertiary. b. Procedures for preparation of derivatives can be found in Ref. 1.

T A B L E 4 Carboxylic acids

Compound

bp, ?C

mp, ?C

MW

Amide

Anilide

Formic acid

100

46 ----

50

Acetic acid

118

60 82

114

Propanoic acid

140

74 81

105

Chloroacetic acid

185

61

94 121

135

2-Chloropropanoic acid

186

108 80

92

Dichloroacetic acid

194

128 98

118

2-Bromopropanoic acid

204

24

153 123

99

Bromoacetic acid

208

50

139 91

131

Octanoic acid

236

144 110

57

Decanoic acid

270

30

172 108 (100)

70

3-Chloropropanoic acid

41

107 101

----

Dodecanoic acid (lauric acid)

43

200 99

78

3-Phenylpropanoic acid

280

48 (40) 110 82 (105)

96

Trichloroacetic acid

57

163 141

97

2-Butenoic acid (trans)

72

86 160

118

Phenylacetic acid

76

136 156

117

2-Benzoylbenzoic acid (monohydrate)

90

208 165

195

(anhydrous, 128) 226

Pentanedioic acid (glutaric acid)

97

132 175 (di)

224 (di)

Phenoxyacetic acid

99

152 101

99

2-Methoxybenzoic acid

100

152 129

----

Citric acid (monohydrate)

100

210 210 (tri)

192 (tri)

(anhydrous, 153) 192

Oxalic acid (dihydrate)

104

126 419d (di)

254 (di)

4-Chlorophenylacetic acid

105

170 175

164

2-Methylbenzoic acid

105

136 142

125

3-Methylbenzoic acid

111

136 94

126

(1)- or (2)-Mandelic acid

118

152 133

151

3-Furancarboxylic acid

121

112 169

----

Benzoic acid

122

122 130

160

Maleic acid

130

116 260 (181) (di) 187 (di)

Cinnamic acid (trans)

133

148 147

153 (109)

2-Furancarboxylic acid

134

112 143

123

Decanedioic acid (sebacic acid)

134

202 210 (di)

202 (di)

To accompany Techniques in Organic Chemistry, Second Edition, by Jerry R. Mohrig, Christina Noring Hammond, and Paul F. Schatz. ? 2006 by W. H. Freeman and Comapny. All rights reserved.

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