[PDF] Tables of Unknowns and Derivatives

[PDF] Tables of Derivatives

2-Ethyl-1-butanol 1-Heptanol 2-Heptanol 1-Hexanol Methanol 4-Methoxybenzyl alcohol 1-Methoxy-2-propanol 4-Methylbenzyl alcohol 2-Methyl-1-butanol

THE OPENING OF TRANS-Z-3-EPOXY-l-BUTANOL DERIVATIVES

THE OPENING OF TRANS-Z-3-EPOXY-l-BUTANOL DERIVATIVES WITH ORGANOMETALLIC REAGENTS Troels Skrydstrup, Michel BMchie and Fraqoise Khuong-Huu*

DERIVATIVES-I - ScienceDirectcom

1965, Vol 21, pp 1647 10 1655 Rrgamon Prws Ltd Printed in Northem Ireland 2,4,4,4=TETRACHLORO- 1 -BUTANOL AND ITS DERIVATIVES-I REACTION WITH AMINES

[PDF] tepzz ¥z74 9b_t - ep 2 307 429 b1

30 jui 2008 · (54) SUBSTITUTED BUTANOL DERIVATIVES AND THEIR USE AS FRAGRANCE AND For example, when the alcohol, 3-methoxy-3-methyl-1-butanol, is

[PDF] Environmental Health Criteria 65 BUTANOLS: FOUR ISOMERS

tert-butanol, all isomers are readily biodegradable and would be expected to be fully oxidised by derivatives, Oxford, Pergamon Press, Vol 2

[PDF] Tables of Derivatives

2-Ethyl-1-butanol 1-Heptanol 2-Heptanol 1-Hexanol Methanol 4- Methoxybenzyl alcohol 1-Methoxy-2-propanol 4-Methylbenzyl alcohol 2-Methyl -1-butanol

[PDF] Chem 353 derivative tables

2-Butanol 99 75 65 97 2-Methyl-1-propanol 108 86 86 104 3-Methyl-2- butanol 113 76 68 110 1-Butanol 116 64 63 71 3-Pentanol 116 101 48 95

[PDF] CHEM 269: ALCOHOLS, ALDEHYDES & KETONES: DERIVATIVE

CHEM 269: ALCOHOLS, ALDEHYDES KETONES: DERIVATIVE MELTING POINTS ALCOHOLS 3,5-DNB KETONES 2,4-DNP 3-methyl-1-butanol 61

[PDF] Tables of Unknowns and Derivatives - Macmillan Learning

appears in the table in place of the derivative's melting point In a few 2-Methyl- 1-propanol 108 86 104 86 1-Butanol 116 64 71 61 3-Pentanol 116 99

PDF document for free

PDF document for free

[PDF] Tables of Unknowns and Derivatives - Macmillan Learning

39375_2mohrig3etalesofunknownsandderivatives.pdf 357

APPENDIX

Tables of Unknowns

and Derivatives The following tables list several hundred organic compounds and provide repre- sentative 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 temper- ature may be in the liquid state when you encounter them due to depression of their melting points by impurities. Remember also that the melting point s 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 d ash 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 poi

nt.To accompany Techniques in Organic Chemistry, Second Edition, by Jerry R. Mohrig, Christina Noring Hammond, and Paul F. Schatz.

358Part 4 • Organic Qualitative Analysis

Alcohols

Compoundbp, °C mp, °C 3,5-Dinitrobenzoate 1-Naphthylurethane Phenylurethane

Methanol6510712447

Ethanol78937952

2-Propanol8312210676

2-Methyl-2-propanol 83 25 142101136

2-Propen-1-ol974910870

1-Propanol97748057

2-Butanol99759765

2-Methyl-2-butanol 1021167242

2-Methyl-1-propanol 1088610486

1-Butanol116647161

3-Pentanol116999548

2-Pentanol1196174ÑÑ

3-Methyl-3-pentanol 12396 (62)8343

2-Methoxyethanol 124ÑÑ112ÑÑ

1-Chloro-2-propanol 12777ÑÑÑÑ

2-Methyl-1-butanol 129708231

3-Methyl-1-butanol 131616855

2-Chloroethanol 1319510151

4-Methyl-2-pentanol 1326588143

2-Ethoxyethanol 1357567ÑÑ

3-Hexanol13597 (77) ÑÑÑÑ

1-Pentanol138466846

2-Hexanol1393860ÑÑ

Cyclopentanol140115118132

3-Hydroxy-2-butanone 145ÑÑÑÑÑÑ

2,2,2-Trichloroethanol 151 19 14212087

1-Hexanol157586042

2-Heptanol1594954ÑÑ

Cyclohexanol161 25 11212982

1-Amino-2-propanol 163ÑÑÑÑÑÑ

4-Hydroxy-4-methyl-

2-pentanone 16655ÑÑÑÑ

2-Furylmethanol 1718013045

1-Heptanol176476260

2-Octanol1793263114

1,2-Propanediol 187ÑÑ153 (di) ÑÑ

1-Octanol194616774

1,2-Ethanediol197169 (di)176 (di) 157 (di)

1-Phenylethanol 202 20 9310692

Benzyl alcohol20511213477

1,3-Propanediol 214178 (di)164 (di) 137 (di)

2-Phenylethanol 21910811978

1-Decanol231577359

3-Phenyl-1-propanol 23692ÑÑ45

Cinnamyl alcohol 257 33 12111490

1-Dodecanol

(lauryl alcohol) 259 24 608074

4-Methoxybenzyl

alcohol259 24 ÑÑÑÑ92

Glycerol290dÑÑ191 (tri) 180 (tri)

( )-Menthol43 153119111

TABLE 1To accompany Techniques in Organic Chemistry, Second Edition, by Jerry R. Mohrig, Christina Noring Hammond, and Paul F. Schatz.

Appendix • Tables of Unknowns and Derivatives359

Alcohols(continued)

Compoundbp, °C mp, °C 3,5-Dinitrobenzoate 1-Naphthylurethane Phenylurethane

2,2-Dimethyl-1-

propanol 113 53 ÑÑ 100 144

Diphenylmethanol

(benzhydrol) 288 69 141 135 139

Benzoin 133 (137) ÑÑ 140 165

( )-Cholesterol148ÑÑ176168 ( )-Borneol208154132138

TABLE 1

Aldehydes

Compoundbp, °C mp, °C 2,4-Dinitrophenylhydrazone Semicarbazone

TABLE 2

Propanal4915089 (154)

2-Butenal (trans)103190199

Hexanal128104106

Heptanal155108109

2-Furancarboxaldehyde 161229 (212)202

Cyclohexane-

carboxaldehyde161172173

Octanal17110698

Benzaldehyde179237222

Phenylethanal194 34121153

2-Hydroxy-

benzaldehyde196248231

4-Methylbenzaldehyde 204232234 (215)

2-Chlorobenzaldehyde 213212225 (146)

3-Phenylpropanal224149127

3-Bromobenzaldehyde 235ÑÑ205

2-Methoxybenzaldehyde 245 38253215d

4-Methoxybenzaldehyde 247254210

Cinnamaldehyde (trans) 252255d215

3,4-Methylenedioxy-

benzaldehyde263 37266d230

3,4-Dimethoxy-

benzaldehyde44262177

4-Chlorobenzaldehyde 214 47254230

4-Bromobenzaldehyde56257228

3-Nitrobenzaldehyde58293d246

4-Hydroxy-3-methoxy-

benzaldehyde (Vanillin)80271d229

3-Hydroxybenzaldehyde104257d198

4-Hydroxybenzaldehyde115280d224To accompany Techniques in Organic Chemistry, Second Edition, by Jerry R. Mohrig, Christina Noring Hammond, and Paul F. Schatz.

360Part 4 • Organic Qualitative Analysis

Amines

CompoundClassabp, °C mp, °C BenzamidebBenzenesulfonamidebPicrateb

TABLE 3

tert -Butylamine1° 46134 - - 198

Propylamine1° 498436135

Diethylamine2° 554242155

Allylamine1° 58 - - 39140

sec -Butylamine1° 637670139

2-Amino-2-methylbutane 1° 77 - - - - 183

Butylamine1° 7742 - - 151

Diisopropylamine2° 83 - - - - 140

Pyrrolidine2° 89 - - - - 112 (163)

Triethylamine3° 89 - - - - 173

1-Aminopentane1° 104 - - - - 139

Piperidine2° 1054893152

Dipropylamine2° 110 - - 5175

Ethylenediamine1° 116244 (di) 168 (di) 233 (di)

1-Aminohexane1° 1294096126

Morpholine2° 13075118146

Diisobutylamine2° 138 - - 55121

2-Aminoheptane1° 143 - - - - - -

1-Aminoheptane1° 155 - - - - 121

Tripropylamine3° 156 - - - - 116

Dibutylamine2° 160 - - - - 59

1-Amino-2-propanol 1° 163 - - - - 142

Indole-3-acetic acid 2° 168 - - - - - -

2-Fluoroaniline1° 176113 - - - -

N,N -Dimethylbenzylamine 3° 182 - - - - 93 N -Methylbenzylamine 2° 182 - - - - 117

Benzylamine1° 18410588194

4-Fluoroaniline1° 186185 - - - -

1-Phenylethylamine 1° 187120 - - - -

2-Phenylethylamine 1° 19811669174

Tributylamine3° 216 - - - - 106

4-Aminomethylpyridine 1° (3°) 230 - - - - - -

Aminodiphenylmethane 1° 295 - - - - - -

2-Amino-6-methylpyridine 1° (3°) 208 41 90 - - 202

2-Benzoylpyridine 3°42 - - - - 130

4-Methylaniline1° 200 45 158120182

2-Aminobiphenyl1°49 102 - - - -

6-Amino-1-hexanol 1°57 - - - - - -

Methoxyaniline1°58 15495 - -

4-Bromoaniline1° 245d 66 204134180

4-Iodoaniline1°67 222 - - - -

2-Nitroaniline1°71 11010473

4-Chloroaniline1°72 192122 - -

Tribenzylamine3°91 - - - - 190

3-Nitroaniline1°113 155136143

2,4,6-Tribromoaniline 1°119 198 - - - -

3-Aminophenol1°122 174 (198) - - - -

3-(Dimethylaminomethyl)-

indole3°133 - - - - - -

2-Aminobenzoic acid 1°146 182 - - 104

4-Nitroaniline1°147 199139100To accompany Techniques in Organic Chemistry, Second Edition, by Jerry R. Mohrig, Christina Noring Hammond, and Paul F. Schatz.

Appendix • Tables of Unknowns and Derivatives361

Amines(continued)

CompoundClassabp, °C mp, °C BenzamidebBenzenesulfonamidebPicrateb

TABLE 3

3-Aminobenzoic acid 1°173 248 - - - -

2-Aminophenol1°174 - - 141 - -

4-Aminophenol1°184 234 (di) 125 - -

4-Aminobenzoic acid 1°189 278 - - - -

? -Alanine1°200d 120 - - - -

Glycine1°230d 188 - - 202

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

Carboxylic acids

Compoundbp, °C mp, °C MW Amide Anilide

TABLE 4

Formic acid10046 - - 50

Acetic acid11860 82114

Propanoic acid14074 81105

Chloroacetic acid185 61 94 121135

2-Chloropropanoic acid186108 8092

Dichloroacetic acid194128 98118

2-Bromopropanoic acid204 24 153 12399

Bromoacetic acid208 50 139 91131

Octanoic acid236144 11057

Decanoic acid270 30 172 108 (100) 70

3-Chloropropanoic acid41 107 101 - -

Dodecanoic acid (lauric acid)43 200 9978

3-Phenylpropanoic acid280 48 (40) 110 82 (105) 96

Trichloroacetic acid57 163 14197

2-Butenoic acid (trans)72 86 160118

Phenylacetic acid76 136 156117

2-Benzoylbenzoic acid (monohydrate)90 208 165195

(anhydrous, 128) 226 Pentanedioic acid (glutaric acid)97 132 175 (di) 224 (di)

Phenoxyacetic acid99 152 10199

2-Methoxybenzoic acid100 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 acid105 170 175164

2-Methylbenzoic acid105 136 142125

3-Methylbenzoic acid111 136 94126

(1)- or (2)-Mandelic acid118 152 133151

3-Furancarboxylic acid121 112 169 - -

Benzoic acid122 122 130160

Maleic acid130 116 260 (181) (di) 187 (di)

Cinnamic acid (trans)133 148 147153 (109)

2-Furancarboxylic acid134 112 143123

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.

362Part 4 • Organic Qualitative Analysis

Esters

Compoundbp, °C mp, °C

TABLE 5

Ethyl formate54

Methyl acetate57

Ethyl trifluoroacetate61

Ethyl acetate77

tert -Butyl acetate98

Propyl acetate101

Allyl acetate103

1-Methylpropyl acetate112

2-Methyl-1-propyl acetate117

Methyl 2-butenoate (

trans )119

1-Butyl acetate126

3-Methyl-1-butyl acetate142

1-Butyl propanoate146

1-Pentyl acetate149

Ethyl 2-oxopropanoate155

Carboxylic acids (continued)

Compoundbp, °C mp, °C MW Amide Anilide

TABLE 4

Acetylsalicylic acid136 180 138136

2-Chlorobenzoic acid140 156 142 (202) 114

3-Nitrobenzoic acid140 167 142153

2-Nitrobenzoic acid146 167 174155

2-Aminobenzoic acid146 136 109131

Diphenylacetic acid148 212 168180

Benzilic acid150 228 153174

2-Bromobenzoic acid150 201 155141

Hexanedioic acid (adipic acid)153 146 220 (di) 240 (di)

3-Chlorobenzoic acid158 156 134122

2-Hydroxybenzoic acid (salicylic acid)159 138 139136

1-Naphthoic acid160 172 203163

2-Iodobenzoic acid162 248 110141

2,4-Dichlorobenzoic acid162 191 194 ÑÑ

(1)-Tartaric acid169 150 195 (di) 263 (di)

4-Methylbenzoic acid180 136 160145

3,4-Dimethoxybenzoic acid182 182 164154

4-Methoxybenzoic acid184 152 167169

Butandioic acid (succinic acid)185 118 260 (di) 230 (di)

4-Aminobenzoic acid189 136ÑÑ

Hippuric acid (

N -benzoylglycine)190 179 183208 ? -Alanine200d 89 ÑÑ ÑÑ

Phthalic acid206d 166 220 (di) 253 (di)

4-Hydroxybenzoic acid215 138 162196

Glycine230d 75 ÑÑ ÑÑ

4-Nitrobenzoic acid241 167 201211

4-Chlorobenzoic acid242 156 179194

Fumaric acid286 116 266 (di) 313 (di)To accompany Techniques in Organic Chemistry, Second Edition, by Jerry R. Mohrig, Christina Noring Hammond, and Paul F. Schatz.

Appendix • Tables of Unknowns and Derivatives363

Esters (continued)

Compoundbp, °C mp, °C

TABLE 5

Ethyl hexanoate168

Ethyl trichloroacetate168

Methyl acetoacetate170

2-Furylmethyl acetate176

Ethyl acetoacetate181

Methyl 2-furoate181

Dimethyl butanedioate196

Phenyl acetate197

Methyl benzoate199

4-Hydroxybutanoic acid lactone 204

Ethyl 4-oxopentanoate206

4-Hydroxypentanoic acid lactone 207

Ethyl benzoate213

Benzyl acetate216

Diethyl butanedioate217

Diethyl (

E )-2-butenedioate218

Diethyl (

Z )-2-butenedioate222

Methyl 2-hydroxybenzoate223

( ? )-Bornyl acetate223 29

Ethyl 2-hydroxybenzoate234

1-Butyl 4-oxopentanoate237

Ethyl decanoate244

1-Butyl benzoate250

Glyceryl triacetate258

Ethyl benzoylacetate265

Ethyl dodecanoate269

Ethyl cinnamate (

trans )271

Dimethyl phthalate284

Dibutyl phthalate340

Benzyl benzoate323 21

Methyl 3-pyridinecarboxylate209 42

Phenyl 2-hydroxybenzoate42

1-Naphthyl acetate48

Methyl 2-hydroxy-2-phenylacetate52

Phenyl benzoate70

Diphenyl phthalate75

Cholesteryl acetate116 (94)

Ethyl 4-hydroxybenzoate116

Acetylsalicylic acid (Aspirin)136To accompany Techniques in Organic Chemistry, Second Edition, by Jerry R. Mohrig, Christina Noring Hammond, and Paul F. Schatz.

364Part 4 • Organic Qualitative Analysis

Ketones

2,4-Dinitrophenyl

Compoundbp, °C mp, °C hydrazone Semicarbazone

TABLE 6

Acetone56126190

2-Butanone80117136

2,3-Butanedione88314 (di) 278 (di)

235 (mono)

3-Methyl-2-butanone94120113

2-Pentanone102144110

3-Pentanone102156139

3,3-Dimethyl-2-butanone (pinacolone) 106125157

4-Methyl-2-pentanone11695133

2,4-Dimethyl-3-pentanone12595160

3-Hexanone125130113

2-Hexanone129106 (110) 12

Cyclopentanone131146210

2,4-Pentanedione139209 (di) 209 (di)

122 (mono)

4-Heptanone14475133

3-Hydroxy-2-butanone (acetoin)145318185 (202)

3-Heptanone148ÑÑ103 (152)

2-Heptanone15189127

Ethyl 2-oxopropanoate155ÑÑÑÑ

Cyclohexanone156162166

4-Hydroxy-4-methyl-2-pentanone166203ÑÑ

3-Octanone167ÑÑÑÑ

2,6-Dimethyl-4-heptanone16866 (92) 126

3-Methylcyclohexanone169155179 (191)

Methyl acetoacetate170ÑÑ152

4-Methylcyclohexanone171134199

2-Octanone17258122

Ethyl acetoacetate18193133

Cycloheptanone181148163

5-Nonanone187ÑÑ90

2,5-Hexanedione194257 (di) 224 (di)

185 (mono)

2,6-Dimethyl-2,5-heptadien-4-one (phorone) 198 27 118221 (186)

Acetophenone204 20 240 (250) 198

Ethyl 4-oxopentanoate206102148

1-Phenyl-2-propanone216 27 156199

Propiophenone218 20 191174

2-Methyl-1-phenyl-1-propanone222163181

1-Phenyl-2-butanone226ÑÑ135 (146)

4-Methylacetophenone226 28 260205

( )-Carvone230191162

4-Chloroacetophenone232231204 (160)

Butyl 4-oxopentanoate237ÑÑÑÑ

4-Methoxyacetophenone258 37 220 (231) 197

Ethyl benzoylacetate265ÑÑ125

1-Acetylnaphthalene302ÑÑ289 (233)

1,3-Diphenylacetone330 33 100146 (126)

2-Benzoylpyridine42 199ÑÑ

Benzoin methyl ether48 ÑÑÑÑTo accompany Techniques in Organic Chemistry, Second Edition, by Jerry R. Mohrig, Christina Noring Hammond, and Paul F. Schatz.

Appendix • Tables of Unknowns and Derivatives365

Ketones (continued)

2,4-Dinitrophenyl

Compoundbp, °Cmp, °ChydrazoneSemicarbazone

TABLE 6

Benzophenone48239 (229) 164

4-Bromoacetophenone51230 (237) 208

2-Acetylnaphthalene53262235

1,3-Diphenyl-2-propen-1-one

(benzalacetophenone)58244170 (179)

Benzoin ethyl ether60 - - - -

4-Methoxybenzophenone62180 - -

4-Nitroacetophenone80 - - - -

3-Nitroacetophenone81228257

Fluorenone83283234

Benzil95189 (di)244 (di)

174 (mono)

2-Benzoylbenzoic acid128 - - - -

Benzoin133 (137) 245206

4-Hydroxybenzophenone134242194

( ? )-Camphor174164247 (237) ( ? )-Camphor180177 - -

Ninhydrin243 - - - -

Phenols

Bromo 1-Naphthyl- 3,5-Dinitro-

Compoundbp, °C mp, °C derivative urethane benzoate

TABLE 7

2-Hydroxybenzaldehyde196 - - - - - -

2-Methoxyphenol (guaiacol)205 32 116 (tri) 118 141

4-Chlorophenol217 37 (43) 90 (di) 166 186

Methyl 2-hydroxybenzoate223 - - - - - -

2-tert-Butylphenol224 - - - - - -

Ethyl 2-hydroxybenzoate234 - - - - - -

Phenyl 2-hydroxybenzoate42 - - - - - -

2-Nitrophenol45 117 (di) 113 155

5-Methyl-2-isopropyl-

phenol (thymol)50 55 (mono) 160 103

4-Hydroxy-3-methoxy-

benzaldehyde (vanillin)80 160 - - - -

1-Naphthol94 105 (di) 152 217

4-tert-Butylphenol100 65 (di) 110 - -

3-Hydroxybenzaldehyde104 - - - - - -

1,2-Dihydroxybenzene

(catechol)106 192 (tetra) 175 152 (di)

1,3-Dihydroxybenzene

(resorcinol)110 112 (di) 206 201 (di)

2-Chloro-4-nitrophenol111 - - - - - -

4-Nitrophenol114 142 (di) 151 186

4-Hydroxybenzaldehyde116 181 (di) - - - -

Ethyl 4-hydroxybenzoate116 - - - - - - To accompany Techniques in Organic Chemistry, Second Edition, by Jerry R. Mohrig, Christina Noring Hammond, and Paul F. Schatz.

366Part 4 • Organic Qualitative Analysis

Phenols (continued)

Bromo 1-Naphthyl- 3,5-Dinitro-

Compoundbp, °C mp, °C derivative urethane benzoate

TABLE 7

1,3,5-Trihydroxybenzene

(phloroglucinol) 117 (dihyd) 151 (tri) - - - -

219 (anhy)

3-Aminophenol122 - - - - 179

2-Naphthol123 84156 210

1,2,3-Trihydroxybenzene

(pyrogallol)133 158 (di) - - 205 (tri)

4-Hydroxybenzophenone134 - - - - - -

2-Hydroxybenzanilide136 - - - - - -

2-Hydroxybenzamide141 - - - - - -

2-Hydroxybenzoic acid

(salicylic acid)159 - - - - - -

4-Acetamidophenol169 - - - - - -

1,4-Dihydroxybenzene

(hydroquinone)171 186 (di) - - 317 (di)

2-Aminophenol174 - - - - - -

4-Aminophenol184 - - - - 178

4-Hydroxybenzoic acid215 - - - - - -

Phenolphthalein265 - - - - - - To accompany Techniques in Organic Chemistry, Second Edition, by Jerry R. Mohrig, Christina Noring Hammond, and Paul F. Schatz.