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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