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7] APPENDIX 1149 respect ultraviolet data are less suitable than infrared data for the " fingerprinting " of substances. The spectrum is characteristic of the chromophoric system rather than that of the complete molecule. 2. Determination of purity. The ultraviolet and visible absorption is often a fairly intensive property; thus e values of high intensity bands may be of the order of 10 4 -10 5 . In infrared spectra e values rarely exceed 10 3 . It is therefore often easy to pick out a characteristic band of a substance present in small concentration in admixture with other materials. Thus small amounts of aromatic compounds can be detected in hexane or in cyclohexsme. 3. Determination of structural features. The ultraviolet spectrum has been of value in the determination of the structure of several vitamins. Thus the presence of an a-naphthoquinone system in vitamin K was first detected by this means. Also the 4-methylthiazole and the 2 : 5-dimethyl- 6-aminopyridine system was first identified in vitamin Bx (thiamine), a- and £-Ionones can be distinguished since the former contains two conjugated chromophores and the latter three conjugated chromophores. 4. Quantitative analysis. Spectroscopic analysis is widely used in the analysis of vitamin preparations, mixtures of hydrocarbons (e.g., benzene, toluene, ethylbenzene, xylenes) and other systems exhibiting characteristic electronic spectra. The extinction coefficient at 326 m[x, after suitable treatment to remove other materials absorbing in this region, provides the best method for the estimation of the vitamin A content of fish oils. 5. Determination of the dissociation constants of acids and bases from the change of absorption spectra with pTL. The spectr<strong>ochem</strong>ical method is particularly valuable for very weak bases, such as aromatic hydrocarbons and carbonyl compounds which require high concentrations of strong mineral acid in order to be converted into the conjugate acid to a measurable extent. 6. Detecting steric hindrance. Hindered rotation about single bonds may be studied. Diphenyls containing bulky oriho substituents can exist as two optical enantiomorphs. For a hindered diphenyl to be resolved, the energy barrier must be of the order of 20 k. cal./mol, but electronic spectra are a much more sensitive test of non-planarity. Thus in orthoditolyl the K band near 250 mpi (present in diphenyl) has completely disappeared and the planes of the two rings must be at an angle of over 45°. The method is therefore of advantage when optical resolution cannot be used as a criterion. 7. Study of reaction rates. The above account of infrared and ultraviolet spectra should provide an introduction to the subject. Further information can be obtained by reference to the books listed below. SELECTED BIBLIOGRAPHY Bellamy, The Infra-Red Spectra of Complex Molecules, 1954 (Methuen). Randall, Fowler, Fuson and Dangl, Infrared Determination of Organic Structures, 1942 (Van Nostrand). Gilman, Organic Chemistry, Volume III, 1953 (J. Wiley ; Chapman and Hall).
1160 PRACTICAL ORGANIC CHEMISTRY [A, Braude and Nachod, Determination of Organic Structures by Physical Methods, 1955 (Academic Press). Strouts, Gilfillan and Wilson, Analytical Chemistry. The Working Tools, Volume II, 1955 (Oxford University Press). Gillam and Stern, An Introduction to Electronic Absorption Spectroscopy in Organic Chemistry, 1954 (Arnold). Braude, Ultra-Violet Light Absorption and the Structure of Organic Compounds {Annual Reports, 42, 105 (1945) }.
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A TEXT-BOOK OF P R A C T I C A L O
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PREFACE TO THIRD EDITION THE favour
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PREFACE TO FIRST EDITION vn the new
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CONTENTS CHAPTER I THEORY OF GENERA
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CONTENTS xiii PAGE 11.58. Apparatus
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CONTENTS xv PAGE 111.76. n-Heptaldo
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CONTENTS xvii PAGE SOME ALIPHATIC D
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CONTENTS xix PAGE DIAZONIUM SALTS 5
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CONTENTS xxi PAGE QUINONES 745 IV,1
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CONTENTS XX1J1 PAGE V,20. n-Amylpyr
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CONTENTS XXV PAGE 1X,7. Diethylbarb
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NAME INDEX OF ORGANIC REACTIONS xxv
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2 PRACTICAL ORGANIC CHEMISTRY [I. e
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4 PRACTICAL ORGANIC CHEMISTRY [I. b
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6 PRACTICAL ORGANIC CHEMISTRY [I. L
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8 PRACTICAL ORGANIC CHEMISTRY [I. r
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10 PRACTICAL ORGANIC CHEMISTRY P. L
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12 PRACTICAL ORGANIC CHEMISTRY [!
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14 PRACTICAL ORGANIC CHEMISTRY [I.
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24 PRACTICAL ORGANIC CHEMISTRY [I,
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34 PRACTICAL ORGANIC CHEMISTRY [1.
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CHAPTER IT EXPERIMENTAL TECHNIQUE 1
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48 PRACTICAL ORGANIC CHEMISTRY [II.
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50 PRACTICAL ORGANIC CHEMISTRY PL h
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52 PRACTICAL ORGANIC CHEMISTRY [II,
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64 PRACTICAL ORGANIC CHEMISTRY III.
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66 PRACTICAL ORGANIC CHEMISTRY [H.
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u PRACTICAL ORGANIC CHEMISTRY [II,
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M PRACTICAL ORGANIC CHEMISTRY [II.
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90 PRACTICAL ORGANIC CHEMISTRY [H,
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96 rRACTICAL ORGANIC CHEMISTRY [II,
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102 PRACTICAL ORGANIC CHEMISTRY [II
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11% PRACTICAL ORGANIC CHEMISTRY PL
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114 PRACTICAL ORGANIC CHEMISTRY rn,
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122 PRACTICAL ORGANIC CHEMISTRY [IL
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138 PRACTICAL ORGANIC CHEMISTRY PL
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156 PRACTICAL ORGANIC CHEMISTRY [M.
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172 PRACTICAL ORGANIC CHEMISTRY [«
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176 PRACTICAL ORGANIC CHEMISTRY in.
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206 PRACTICAL ORGANIC CHEMISTRY [">
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228 PRACTICAL ORGANIC CHEMISTRY [11
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234 PRACTICAL ORGANIC CHEMISTRY [HI
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246 PRACTICAL ORGANIC CHEMISTRY [IU
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250 PRACTICAL ORGANIC CHExMISTRY [H
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252 PRACTICAL ORGANIC CHEMISTRY fil
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TABLE 111,27. Alcohol Diacetone alc
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TABLE 111,42, Halide ALIPHATIO HALO
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TABLE 111,42. ALIPHATIC HALOGEN COM
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TABLE 111,70. Formaldehyde Aldehyde
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344 PRACTICAL ORGANIC CHEMISTRY [Hi
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TABLE III, 74. ALIPHATIC KETONES Ke
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TABLE 111,85. ALIPHATIC CARBOXYLIC
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394 PRACTICAL ORGANIC CHEMISTRY I H
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396 PRACTICAL ORGANIC CHEMISTRY TAB
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412 PRACTICAL ORGANIC CHEMISTRY [in
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TABLE 111,123. Amine Methylamine Et
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TABLE 111,132. AMINO ACIDS—Contin
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TABLE 111,136. POLYHYDRIC ALCOHOLS
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LACTOSAZONE MALTOSAZONE CELLOBIOSAZ
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CHAPTER IV AROMATIC COMPOUNDS AROMA
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510 PRACTICAL ORGANIC CHEMISTRY [IV
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TABLE IV,9. Hydrocarbon Diphenyl .
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530 PRACTICAL ORGANIC CHEMISTRY Liv
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TABLE IV.28. AROMATIC HALOGEN COMPO
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552 PRACTICAL ORGANIC CHEMISTRY [VI
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562 PRACTICAL ORGANIC CHEMISTRY (IV
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TABLE IV,100A. Amine Aniline . o-To
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TABLE IV,100A. PRIMARY AROMATIC AMI
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TABLE IV,100C. Amine p-Bromodimethy
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668 PRACTICAL ORGANIC CHEMISTRY tiv
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TABLE IV,106. AROMATIC ETHERS (cont
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TABLE IV,114. PHENOLS (continued) P
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TABLE IV,U4A. ENOLS Compound Acetyl
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702 PRACTICAL ORGANIC CHEMISTRY LIV
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718 PRACTICAL ORGANIC CHEMISTRY tiv
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TABLE IV,135. AROMATIC ALDEHYDES [c
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TABLE IV,148. Ketone Benzophenone p
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TABLE IV,152. Quinone Thymoquinone
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TABLE IV.175. Add Benzoic o-Toluic
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TABLE IV,205. Alcohol Benzyl P-Phen
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CHAPTER V SOME HETEROCYCLIC AND ALI
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830 PRACTICAL ORGANIC CHEMISTRY [V,
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834 PRACTICAL ORGANIC CHEMISTRY [V.
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888 PRACTICAL ORGANIC CHEMISTRY IV1
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910 PRACTICAL ORGANIC CHEMISTRY IVI
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CHAPTER IX SOME PHYSIOLOGICALLY ACT
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998 PRACTICAL ORGANIC CHEMISTRY [IX
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1000 PRACTICAL ORGANIC CHEMISTRY [I
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1010 PRACTICAL ORGANIC CHEMISTRY fi
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CHAPTER X SYNTHETIC POLYMERS X,l. B
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1016 PRACTICAL ORGANIC CHEMISTRY [X
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CHAPTER XI QUALITATIVE ORGANIC ANAL
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1034 PRACTICAL ORGANIC CHEMISTRY 1X
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1074 PRACTICAL ORGANIC CHEMISTRY IX
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1088 PRACTICAL ORGANIC CHEMISTRY TA
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1090 PRACTICAL ORGANIC CHEMISTRY IX
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Page 1177 and 1178: TABLE A,8,2. 1 PER CENT. CH8OH BY 1
Page 1179 and 1180: TABLE A,8,5. AQUEOUS NITRIC ACID PE
Page 1181 and 1182: TABLE A,8,9. PER CENT. HBr BY WEIGH
Page 1183 and 1184: TABLE kfi,12. AQUEOUS AMMONIA SOLUT
Page 1185 and 1186: TABLE A,8,/6. AQUEOUS POTASSIUM CAR
Page 1187 and 1188: A,9. DENSITY AND VAPOUR PRESSURE OF
Page 1189 and 1190: INDEX Page numbers in bold-faced ty
Page 1191 and 1192: a-Amino-n caproic acid, 427, 432 4-
Page 1193 and 1194: a-Benzilmonoxime, 720 P-Benzilmonox
Page 1195 and 1196: m-Chlorobenzoic acid, 929, 932 o-Ch
Page 1197 and 1198: Diethylaniline, 562, 573 purificati
Page 1199 and 1200: p-Ethylbenzyl chloride, 540 Ethyl b
Page 1201 and 1202: Halogen carriers, 533 Halogen compo
Page 1203 and 1204: Magnesium sulphate, as desiccant, 4
Page 1205 and 1206: m-Nitroaniline, 563, 574 7>-Nitroan
Page 1207 and 1208: a-Picoline, purification of, 177 p-
Page 1209 and 1210: Semimicro apparatus—cord, distill
Page 1211 and 1212: Thermometers, 72 calibration curve
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