None
In contact with penicillium glaucum, a solution of inactive leucine becomes levorotatory owing to the destruction of the dextro modification (compare p. 557) ; Z-leucine has properties identical with those of natural leucine, except, of course, that it is levorotatory. Creatine, NH:C(NH2)-N(CH3)-CH2-COOH, is a very im- portant substance found in the muscles, nerves, and blood, and also in considerable quantity in meat extract, from which it was isolated by Chevreul in 1834. Muscles contain about 0-3 per cent, of creatine, and it has been calculated that the total muscles of a full-grown man contain no less than 90-100 grams of this substance. The name creatine is derived from xpfas, meat. Pre^a?-afo'o».— Meat extract (40 grams) is dissolved in water (800 giams), and basic lead acetate added until no further pre- cipitate is produced ; the filtrate is freed from lead by passing hydrogen sulphide, and, after filtering, concentrated to about 40 cc. Tlie crystals whicli separate are washed with dilute alcohol (88 per cent.) and purified by crystallisation from water. Creatine crystallises from water in colourless prisms con- taining one molecule of water, which is driven off at 100°; it is moderately soluble in water, but very sparingly in alcohol. It has a neutral reaction and a bitter taste, and forms salts with 1 equivalent of an acid, but it does not appear to possess acid properties. When boiled with acids it is con- verted into creatinine (p. 604), and when digested with baryta water it is decomposed into urea and sarcosine, 604 APPENDIX. NH:C(NH2).N(CH3)-CH2-COOH + H^O = NHj-CO-NHg + NH(CH3).CH2.COOH. Creatine has been prepared synthetically by heating to- gether cyanamide and sarcosine in alcoholic solution, NiC-NHa + HN(CHg).CH2-C00H = NH:C(NH2)-N(CH3>CH2.COOH. ^^NH CO Creatinine, NH:C\ | the anhydride (lactam) \N(CH3).CH2, of creatine, is formed, as mentioned above, by the action of acids on the latter, and it is reconverted into creatine by treatment with alkalis. It is found in considerable quantities in urine (about 0-25 per cent.), and is also present in the muscles, especially after great exertion ; in both these cases it is evidently produced from creatine. Creatinine crystallises in prisms, and is much more soluble in water than creatine ; it is a strong base, and yields salts such as the hydrochloride C4HyN30,HCl, with I equivalent of an acid. When zinc chloride is added to its solution in water a highly characteristic, sparingly soluble compound, {G^-fNfi)2,ZnGl2, separates in the form of fine needles, and this compound is used in the quantitative determination of creatinine. Creatinine reduces Fehling's solution (part i. p. 268), and gives, with phosphomolybdic acid (p. 501), a yellow crystalline precipitate. NHg-CH-COOH Asparagine, or amidosuccinamic acid, CHa-CO-NHj, contains an asymmetric carbon atom, and therefore exists in two active modifications, both of which have been prepared. l-Asparagirw, the more important modification, is formed in the decomposition of proteids. It occurs in many plants, particularly in asparagus, and in the young shoots of beans. APPENDIX. 605 peas, and lupines, from which it may be obtained by extraction with water. It crystallises from water, in which it is readily soluble, in glistening prisms, and is sparingly soluble in alcohol and ether ; the aqueous solution is levorotatory, but becomes dextrorotatory on the addition of hydrochloric acid. When treated with acids or alkalis, asparagine is converted into ;-aspartic acid, COOH-CH(]S'H5).CH2-COOH (part i. p. 245). d-Asparagine occurs together with Z-asparagine in the young shoots of lupines, and is, of course, identical with the latter in all ordinary properties. It is noteworthy that when mixed in equal quantities in aqueous solution d- and Z-asparagine do not, like the tartaric acids, combine to form an inactive modification, but the solution, on evaporation, deposits crystals of the two active modifications side by side. When treated with hydrochloric acid, tZ-asparagine yields tZ-aspartic acid. Tyrosine, or Tp-hydroxyplienyl-a-amidopropionic acid, OH-C6H^-CH2-CH(NH2).COOH, is formed together with leucine (p. 602) in the decomposition of proteids ; it is found in the liver in some diseases, in the spleen, pancreas, and in cheese (the name is derived from Tvpo^, cheese) ; it was first prepared by Liebig in 1846 by fusing cheese with potash. Tyrosine crystallises in silky needles, which are sparingly soluble in water and alcohol, and almost insoluble in ether ; it combines with both acids and bases to form salts. When its aqueous solution is mixed with a solution of mercuric nitrate, a yellow j)recipitate is produced, which when boiled with dilute nitric acid acquires an intense red colour; this reaction is used as a delicate test for tyrosine. Tyrosine decomposes at 270° into carbonic anhydride and Tp-hydroxyphenylethylamine, OH-CgH^-CHg-CHj-NHg, and when fused with potash it yields j)-hydroxybenzoic acid (p. 451), acetic acid, and ammonia. The constitution of this substance is cleaily indicated by these reaetions, and is proved by the following synthesis which was 606 APPENDIX. carried out by Erlenmeyer and Lipp. Phenylaoetaldeliyde,* CjHj-CHj-CHO, yields, with hydrocyanic acid, the nitrile of phenyllactie acid, CsHs-CHj-CHIOHl-CN. When this compound is heated with alcoholic ammonia on the water-bath, the hydroxyl is displaced by the amido-gronp, and the nitrile of phenylamido- propionic acid, C6H5-CH2-CH(NH3)-CN, is formed ; this nitrile, on hydrolysis, yields phenylamidopropionic acid (phenylalanine), C6H5-CH2.CH(NH2)-COOH. Nitric acid converts this amido-acid into p-nitrophenylamMo- propionic acid, N02-C6H4-CH2-CH(NH2)-COOH, from which, on reduction, the. corresponding amidophenylamidopropionic acid is ' obtained ; the latter, on treatment with nitrous acid, yields tyrosine. Compounds of Unknown Constitution found in Bile. Most of the important compounds of animal origin of known constitution having been described, this section inchides some rather more complex substances of unknown constitution, which are classed together merely because they occur together in bile. The bile contains, besides lecithine (p. 588) and colouring matters, %wo remarkable acids called glycocholic acid and taurocholic acid, and an alcohol named cholesterine. GUycochoIic acid, Cg^HagO^-NH-CHj-COOH, crystallises in colourless needles, and melts at 133°; it is soluble" in water and alcohol, but very sparingly soluble in ether j its alcoholic solution is dextrorotatory. It occurs in bile in the form of its sodium salt, C2eH^2-^^-'^^6> '"'liich crystallises in stellate groups. Preparation. — Fresh bile is mixed with a few drops of hydro- chloric acid and rapidly filtered through sand. The filtrate is mixed with concentrated hydrochloric acid and ether, in the pro- portion of 5 vols, of the former and 30 vols, of the latter to 100 vols. * Phenylacetaldehyde, CsHs-CHs-CHO, is prepared by distilling a mixture of the calcium salts of phenylacetic and formic acids. It is a colourless oil, boiling at 206°, and has properties very similar to those of the aldehydes of the fatty series. APPENDIX. 607 of bile. The crystals of glyoocholic acid, which separate on stand- ing, are washed with water containing hydrochloric acid and ether. Taurocholio acid is contained in the mother-liquors. When boiled with alkalis, glycocholic acid yields cholalia acid and glycine, CaAgOi-NH-CHg-COOH + H^O = G^JL^fi^ + NHj-CHg-COOH. Taurocholic acid, Cj^HggO^-ISrH.CHgCHs.SOgH, occurs in human bile, and generally in the bile of all carnivora. It crystallises in silky needles, is readily soluble in alcohol, and is dextrorotatory. Like glycocholic acid, it occurs in bile in the form of the sodium salt CjeH^NaNO^S. When boiled with water it is decomposed into cholalic acid and taurine, CaAsO^-NH-CHa-CH^-SOgH + H^O Taurocholic Acid. = CatH^oOj 4- NH2-CH2.CH2.SO3H. Cholalic Acid. Taurine. Cholalic acid, C24H4QO5, crystallises in glistening plates, which are sparingly soluble in water, readily in alcohol and ether ; its solutions are dextrorotatory. The only known de- composition which throws any light on the constitution of this interesting acid is the fact that when oxidised with per- manganate it yields acetic acid and o-phthalic acid. Taurine, or amidoisoetMordc acid, NHg-CHj-CHj-SOgH, was discovered by Gmelin in 1824 in oxgall (hence the name from Tavpos, an ox), in which it occurs in the form of tauro- cholic acid (see above). Taurine crystallises in prisms which dissolve readily in water, but are insoluble in absolute alcohol ; it reacts neutral, but forms salts such as the sodium salt NHg-CHg-CHg-SOgNa, with bases. Taurine has been prepared synthetically by carefully treating alcohol with sulphur trioxide, when iscethionic acid is produced, CHg-CHj.OH + SO3 = SOgH.CH^.CHg.OH. This crystalline and very hygroscopic acid, on treatment 608 APPENDIX. with phosphorus pentachloride, yields chlorethylsulphonic acid, CHgCl-CHj-SOgH, from which, by ti'eating -with ammonia, taurine is obtained. Cholesterine, Cj^H^j-OH, is an alcohol which occurs in bile and in the brain, and in considerable quantities in gall- stones and in cancerous and tubercular deposits ; it is also found in the yolk of egg, in the fat obtained from wool, and in guano.* It is readily obtained by extracting gall-stones with absolute alcohol and evaporating the extract ; the residue is purified by treatment with alcoholic potash, which removes extraneous matter, and then crystallised from a mixture of ether and alcohol. Cholesterine crystallises from water in colourless needles, melts at 145°, and distils at about 360° without decomposing appreciably. Reactions of Cholesterine. — If a few centigrams of cholesterine are dissolved in chloroform (2cc.) and tlie solution shaken with concentrated sulphuric acid (2 cc), the chloroform solution is coloured red and then purple, and the sulphuric acid acquires a green fluorescence. If a few drops of the chloroform solution are poured into a dish the colour changes to blue, then to green, and lastly to yellow. Concentrated sulphuric acid containing a little iodine colours cholesterine first violet, then blue, then green, and lastly red. Warmed with dilute (20 per cent.) sulphuric acid, cholesterine crystals are coloured red on the edges. HcBmoglohins. Haemoglobin is the name given to the pigment of the red corpuscles of the blood. 'It exists in the blood in two con- ditions ; in arterial blood it is loosely combined with oxygen, and is called oxyhoemoglohin ; the other condition is the deoxygenated or reduced haemoglobin (often simply called hmmoglohin), which occurs in venous blood — that is, the blood * A substance very similar to cholesterine, and named paracholesterine or phytosterine, is found in the seeds of certain plants. APPENDIX. 609 which is returning to the heart, after it lias supplied the tissues with oxygen. Hsemoglohin is thus the oxygen-carrier of the body, and it may be called a respiratory pigment.' * Oxyhmmoglohin can be obtained from defibrinated blood by mixing it with salt solution (1 vol. of saturated salt solution to 9 vols, of water), which precipitates the blood-corpuscles. These are washed with salt water of the same strength, mixed with a little water, and extracted with ether, which removes cholesterine, &c., all these operations being conducted as nearly as possible at 0°. The ethereal solution is decanted, the aqueous solution fil- tered, the filtrate mixed with one-fourth of its vol. of alcoliol, and cooled to - 10°, when crystals of oxyhjemoglobin separate. These can be purified by again dissolving in water, adding alcohol, and allowing to stand at 0°. ^ Oxyhaemoglobin crystallises in light-red rhombic plates, which dissolve readily in water and are re-precipitated by alcohol. On analysis it gives results which agree closely with those obtained in the analysis of albumin (p. 612), except that oxyhsemoglobin always contains 0-4 per cent, of iron. If the aqueous solution of oxyhsemoglobin is placed in a vacuum, or treated with weak reducing agents, it loses oxygen and is converted into hmmoglohin, a substance which has also been obtained in a crystalline form ; and vice versa, an aqueous solution of haemoglobin is rapidly converted into oxyhsemoglobin in contact with air. If carbonic oxide is led into a solution of oxyhsemoglobin this substance loses its oxygen and combines with the carbonic oxide to form carbonic oxide hmmoglohin, a com- pound which crystallises in large bluish crystals. This compound is not capable of absorbing and giving up oxygen like haemoglobin — a fact which explains the poisonous action of carbonic oxide, since this gas by combining with the oxyhsemoglobin prevents the aeration of the blood. Oxyhsemoglobin, hsemoglohin, and carbonic oxide hemoglobin all show characteristic absorption spectra, * Halliburton, Chemical Physiology, p. 267. 2 M 610 APPENDIX. which allow of their heing easily identified and distinguished from one another. Hsemiu and Hsematein. — When oxyhsemoglobin or dried blood is warmed with a drop of acetic acid and a small crystal of common salt on a microscopic slide, a mass of reddish-brown crystals separates on cooling. These consist of hcemin, the chloride of hsematein, and have the composition CgjHjjN^OjFeCl. If these crystals are treated with alkali, brownish-red flecks of Iwematein, CgjHgjE'^OgFe-OH, separate; and this formation of heemin and haeniateiu serves as a very delicate test for blood. The Proteids or Albuminoids. The substance known as 'white of egg,' or egg-albumin, when separated from the yolk, membrane, and shell, is a colourless, transparent, thick, sticky fluid, soluble in or miscible with water ; on exposure to the air it rapidly loses in weight owing to evaporation of the water contained in it, and if dried artificially it quickly shrivels up, giving a translucent amorphous solid. When white of egg is put into boiling water it undergoes a remarkable change, and is said to have coagulated ; it is now insoluble in water and opaque, and forms a solid mass, which, however, still contains a large percentage of water; during coagulation it is probable that chemical as well as physical changes have occurred. When white of egg is left exposed to the air under ordinary (non-sterile) conditions it soon begins to putrefy — that is to say, it decomposes under the influence of organisms, yielding a great number of products, amongst which are the ptomaines or toxines already described. Further, when white of egg is heated with dilute mineral acids or with alkalies it again undergoes profound decomposition, giving ammonia, carbon dioxide, and a number of other compounds, such as glycine, leucine, tyrosine, &c, APPENDIX, 611 This brief account of the behaviour of white of egg will suffice to show that it is an extremely \mstable and complex substance, and its physical properties are so indefinite that it would be almost impossible to say whether or not it is a definite chemical compound. Now, white of egg, or egg-albumin, may be taken as the representative of a group of substances which are classed together as the prote'ids or albuminoids. These substances form not only the most important part of the contents of the cells of all animals (Trpanlov, pre-eminence), but they also occur in considerable quantities in all plants, especially in the seeds or grain ; it is, in fact, from these vegetable prote'ids that those contained in animals are formed, since the animal, unlike the plant, is incapable of building up more complex substances from simpler food material, except to a very limited extent. The vegetable proteids, then, are assimilated by animals, and apparently they are changed very little during this process. As practically nothing is known of the constitution of these proteids, any attempt to define exactly what is meant by this -term would meet with little success. Proteids differ in physical properties and in behaviour towards various reagents, and these slight differences may be temporarily made use of in order to subdivide them into various groups. As regards their chemical behaviour little can be said, except that they all give a similar complex mixture of products when decom- posed by organisms or by purely chemical agents. There are, however, two statements which are true of all proteids : firstly, they are extremely complex compounds ; and, secondly, they all consist of the five elements, carbon, hydrogen, oxygen, nitrogen, and sulphur. The determination of the percentage composition of a proteid is itself a task of considerable difficulty. As found in nature, all proteids contain mineral matter, and consequently leave on ignition a small percentage of ash ; after the removal of these mineral constituents by repeated precipitation, 612 APPENDIX. dialysis, &c., or allowing for their presence in calculating the result, the percentage composition of the various proteids is found to vary within fairly wide limits, as shown by the following numbers : Carbon 50 -55 percent. Hydrogen 6-9- 7-3 .. Nitrogen 15 -19 n Oxygen 19 -24 n Sulphur 0-3- 2-4 i. JEgg-albumin has been obtained free from mineral matter and in a crystalline condition; its composition is 0 = 51-48, H = 6-76, N = 18-14, O = 22-66, S = 0-96 per cent. The empirical formula calculated from the percentage composition of egg-albumin or from that of some other members of the group of proteids comes out to something like Oi45H226N'44S05|,. This formula, which requires 0 = 51-2, H = 6-6, N=18-0, S = 0-9 per cent., cannot be regarded as having much value, as a very slight difference in the analytical results would make a very great difference in the forrdula. The molecular formulae of the proteids are unknown ; attempts have been made to determine the molecular weight of some of them by the freezing-point method (part i. p. 42), and the results, which are very uncertain, seem to show that egg-albumin may have a molecular weight of 15,000 — a number which will afford an idea of the great complexity of the proteids. The proteids are insoluble in alcohol and ether, and mostly also in water; but many of them dissolve in salt solutions, and the presence of salts probably accounts for their remaining dissolved in the fluids of the animal body. One of the most interesting properties shown by many of the proteids is that of undergoing coagulation, a change which is readily brought about by heat, different proteids coagulating at somewhat different temperatures, varying roughly between APPENDIX. 613 55° and 75° ; some proteids are also coagulated by alcohol and by mineral acids. Those proteids which are coagulated by heat are, for convenience' sake, divided into two groups : (a) Albumins, soluble in water and in solutions of salt or magnesium sulphate. (&) Glohulins, insoluble in water, but soluble in solutions of salt or magnesium sulphate. To the former class belong egg-albumin and serum-albumin; to the latter fibrin-globulin. Those proteids which are not coagulated by heat are divided into : (a) Albuminates, insoluble in water and in salt solutions, but readily soluble in mineral acids and in sodium carbonate; these substances are produced by the action of alkalis on the albumins, globulins, &c. (b) Albumoses and Peptones. When proteids are subjected to the action of the gastric or pancreatic juices, they are first converted into colbumoses,* and finally into peptones, Albumoses are mostly soluble in water and salt solutions ; they are precipitated by alcohol, nitric acid, and ammonium sulphate solu- tion. Peptones are soluble in water, and are precipitated by alcohol, but not by nitric acid or ammonium sulphate solution. Besides those mentioned above, there are several other classes of proteids, for a description of which works on Physiological Chemistry must be consulted. "When subjected to hydrolysis with mineral acids or baryta water, proteids yield, besides ammonia and carbonic anhy- dride, varying quantities of amido-acids of both the fatty and aromatic series, such as glycine (part i. p. 299), leucine * Also called proteoses or propeptones. 614 APPENDIX. (p. 602), tyrosine (p. 605), aspartic acid (p. 605), and P-phenyl-a.-amidopropionic acid {phenylalanine), C6H5-CH2-CH(NH2)-COOH. Under the putrefying influence of certain organisms, pro- teids yield, besides fatty acids, phenylacetie acid (p. 442) and phenol, substances of more complicated structure, such, as indole, CgH^N, and sJcatole, CgHgN. Tests for Proteids. — All proteids are coloured violet-red by a solution of mercuric nitrate containing traces of nitrous acid. This reagent (called Millon's reagent) is prepared by dissolving one part by weight of mercury in two parts of strong nitric acid and diluting the solution with twice its bulk of water ; after standing some time the supernatant lic[uid is decanted from the precipitate. When nitric acid is added to a proteid a yellow colour is produced, which on the addition of ammonia becomes bright orange. Tliis reaction, called the xanthoproteic reaction, is stated to be the most delicate test for proteids. If a few drops of copper sulphate solution are added to a proteid, and then excess of caustic potash, a red to violet colouration is produced. This reaction is called the biuret reaction, because it resembles the colour-reaction obtained under similar circumstances with biuret.* Gelatin is a substance somewhat similar in composition to egg-albumin, but containing only carbon, hydrogen, nitrogen, and oxygen ; it may be obtained by the action of dilute acids on the white fibres of connective tissue. It is best prepared by digesting bones, first with dilute acids to remove inorganic matter, and then with water under pressure at 110-120° ; the solution after filtering and evaporating yields commercial gelatin. Gelatin is a hard, almost transparent, horn-like substance which is insoluble in alcohol, ether, and in cold water, but * When urea is heated at about 156° ammonia is evolved and the residue Contains biuret, 2KKj-C0'NHs = NH2-CO'NH-CO-NH2+ NH3, a crystalline substance (m.p. 190°), readily soluble in alcohol and water; the formation of biuret (the presence of which can be shown with the aid of the above colour-reaction) affords a very useful test for urea. APPENDIX. 615 dissolves readily in hot water^ yielding a solution which, on cooling, sets to a jelly {gelatinises). If, however, the aqueous solution is boiled for some hours the power of gelatinising is entirely destroyed. Gelatin forms an insoluble compound with tannic acid, and the process of tanning consists partly in converting the gelatin in the hides into this hard insoluble compound by steeping them in tannic acid solution. When digested with dilute sulphuric acid gelatin breaks down much in the same way as the proteids yielding glycine, leucine, and other fatty amido-acids. IJSTDEX. [Where more than one reference is given, and one of tlietn is in heavy type, the latter refers to the systematic description of the substance.] PAGE Acetal 127 Acetaldehyde 84, 96, 122 Acetaldehydeliydrazone 136 Acetaldoxime 124, 134 Acetals 143 Acetamide 164 Acetanilide 372, 374 Acetic acid 96, 149 Acetic acid, electrolysis of. 58 Acetic acid, salts of. 153 Acetic anhydride 163 Acetic ether 189 Acefcoacetic acid 193, 199 Acetone 89, 130 Acetone cyanohydrin 142 Acetone dichloride 142 Acetone hydrazone 136 Acetone mercaptole 188 Acetone pinacone 141 Acetone sodium bisulphite . ./. 131 Acetonedicarboxylic acid 253 Acetonitrile 164, 294 Acetophenone 423 Acetophenonehydrazone 424 Acetophenoneoxime 424 Acetotoluidide 372 Acetoxime 135 Acetyl chloride 161 Acetylbenzene 423 AcetylceUulose 282 Acetylcodei'ne 510 Acetylene 72, 81 Acetylene series 80 Acetylformic acid 200 Acetyl fructose 271 Acetylglucose 268 /3-Acetylpropionic acid 200 Acid amides 164, 169 PAGE Acid anhydrides .162, 169 Acid bromides 162 Acid chlorides 161, 169 Acid dyes 518 Acid green 522 Aconitic acid 253 Acraldehyde 262 Acrolein 255, 261, 262 Acrolein bromide 263 <K-Acrose 272 Acrylaniline 495 Acrylic acid 263 Active aniyl alcohol 106, 544, 545 Additive products 77 Adipicacid 235, 244 Alanine 301 Alcohol 94 Alcohol, determination of. 102 Alcohol, manufacture of. 100 Alcoholic liquors 103 Alcoholometry 101 Alcohols, monohytlric 89, 414 Alcohols, nomenclature of. 103 Alcohols, oxidation of 110 Alcoliols, polyhydric 253, 264 Alcohols, trihydric 253 Aldehyde ammonia 124 Aldehyde cyanohydrin 142 Aldehyde resin 124 Aldehydes * US, 417 Aldehydes, condensation of. 144 Aldehydes, oxidation of. 142 Aldol 126 Aldoximes 134 Aliphatic compounds 332 Alizarin, 478 ; diacetate, 4S0 ; dyeing with , -. 516 Alkali blue. 629 618 INDES. FAOE Alkaloids, 497 ; extraction of 499 Alkaloids, contained in opium, 508; derived from pyridine, 501; derived from quinoline, 504; related to uric acid 510 Alkyl chlorides 117 Alkyl cyanides 293 Alkyl hydrides 117 Alkyl hydrogen sulphates 80, 185 Alkyl isocyanates , 296 Alkyl radicles 117 Alkylauilines 377 Alkylene radicles 117 AUeue 86 Allyl alcohol 260 Allyl bromide 262 Allyl iodide 261 Allyl isothiocyanate 262, 298 Allyl sulphide 262 Allyleue 81, 86, 87 Aluminium ethyl 223 Amalinic acid 510 Amides 164 Amidoacetic acid 229, 299 Amido-acids 299 Amidoazobenzene, 387, 533, 535 ; sul- phouic acid. 534 Amidoazo-compounds 386 Amidoazotoluene hydrochloride 534 Amidobenzaldehydes 421 Amidobenzene 373 Amidobenzenesulphonic acids . . .396, 397 Amidobenzoic acid 435, 450, 540 Amido-compounds 368 Amidoethyl alcohol 439 Amidoethylsul phonic acid. 513 Amidoformic acid 301 Amidonaphtlialene 457, 465 »- Amido-/3-naphthol 468 l:4-Amidonaphthol 468 Amidophenol 427 Aniidopropionic acid 232, 301 Amidotoluene 376 Amines 204, 380 Amines, separation of primary, secondary, and tertiary 213 Amygdalin 287, 418 Aniyl acetate / 193 Amyl alcohol, 106, 107, 545 ; cyanide, 545 ; iodide, 645 ; nitrite 184 Amyl alcohols 106 Amyl hydrogen sulphate 106 FAOd Amylene 78 Amylum 278 Anethole '. 423, 462 Anhydrides 162 Aniline, 373 ; homologues of, 376 ; substitution products of, 376 ; sul- phonic acid ^ 396 Aniline blue 529 Aniline yellow 635 Animal charcoal 7 Anisaldehyde 417, 423 Anisic acid 417, 423, 452 Anisole 405 Anisyl alcohol 417,423 Anthracene 308, 338, 470 Anthracene derivatives, isomerism of 475 Anthracene dichloride 475 Anthracene disulphouic acids 478 Anthracene oil 308 Anthracene picrate 471 Anthranilic acid 435, 450, 540 Anthranol 477 Anthrapurpurin 481 Anthraquinone 476 Anthraquinone-/3-monosulphDnic acid 477, 479 Anthraquinonedisulphonic acid 481 Anthraquinonesulpbonic acid, sodium salt of. 478 Antifebrin 374 Antipyrine 511 Arabinose 264 Arabitol 264 Arbutin 411 Argol 247 Aromatic, alcohols, 414; aldehydes, 417 ; amines, 380 ; compounds, general properties of, 331 ; halo- g6n_ derivatives 352 Arsines 215 Aseptol 408 Asparagin 245 Aspartic acid 245 Asymmetric carbon atom ,. . . ; 544 Atropine , 503 Aurin 524, 530 Azobenzene 391, 514, 533 Azobenzenesulphonic acid 533 Azo-corapounds 390, 533 Azo-dyes 583, 634, 535 Azoxybenzene 390 INDEX. 619 PAGE Azoxy-com pounds 390 Azulmic acid 286 Ballistite 282 Barley-sugai- ^ 275 Basic dyes 518, 534 Baumann and Schotten's metliod 433 Beer, preparation of. 98 Beiizal chloride 362, 418 Benzaldeliyde 418 Benzaldehyde green 522 Benzaldoxime 419 Benzaniide 433 Benzene, 85, 3,07, 308 ; constitution of..313 Benzene derivatives, isomerism of 313 Benzene hexabromide 313 Benzene hexachloride 313 Benzene liexahydride 335 Benzene, homologues of. 339 Benzene, synthesis of. 311 Benzeiie-r?i-dicarboxylic acid 439 Benzene-o-dicarboxylic acid 438 Benzene-j)-dicarboxylic acid 440 Benzenedisulplionic acid 396 Benzenesulphonamide 396 Benzenesulphonic acid 395 Benzenesulphonic chloride 396 Benzidine 391, 537 Benzil 420 Benzine '^^ Benzoic acid, 430; salts of, 431; substitution products of 434 Benzoic anhydride 432 Benzoin 420 Benzonitrile 433 Benzophenone 351, 424 Benzopurpurin 538 Benzoquinone 425 B en zotri chloride 362 Benzoyl chloride 432 Benzoyl derivatives 433 Benzoylbenzene 424 Benzoylbenzoic acid 476 Benzoylglycine 300 Benzoyl-group 432 Benzyl, acetate, 361, 416 ; alcohol, 415 ; bromide, 415 ; chloride, 353, 355, 361, 418, 474; cyanide, 442; radicle 344 Benzylamine 380 Benzylidene radicle 420 Benzylideneacetone 420 PAGE Benzylidenehydrazone 419 Benzylidenehydroxycyanide 420 Benzylmalonic acid 442 Betaine, 512 ; chloride 513 Bioses 266, 283 Bismarck brown 536 Bismuth, alkyl compounds of 217 Boiling-point 9 Bone-oil, Bone-tar 485 Bordeaux 537 Brilliant green 522 Bromacetic acids 166 Bromacetylene 333 Bromanthraquinone 476 Bromethane 179 Bromethylamine 439 Bromethylene 77 Bromethylphthalimide 439 Bromination of acids 167 Bromine, detection of. 16 Bromine, estimation of 27 Bromobenzene 358 Bioinobenzoic acids 435 Bromobenzoylbenzoic acid 476 Bromobeiizyl bromide 474, 482 Bronioform ,. ..178 Bromohexabydrobenzene 335 Bromohexamethylene 335 Bromonaphthalenes 463 Bromonitrobenzenes 367 Bromoplithalic acid, anhydride 476 «-Bromopropionic acid 231, 232 /3-Bromopropionic acid 233 Broniosuccinic acid 245 Bromotoluene 474 Brucine, 507 ; methiodide ; .508 Butaldehyde 129, 137 Butane 61, 67 Butter 173 Butyl alcohol, normal 104, 106 Butyl chloral 129 Butyl chloral, hydrate 129 Butyl iodide 180, 181 Butyl iodide, secondary 80 Butyl iodide, tertiary 181 Butylamine 211 «-Butylene 78 /3-Butylene 78 y-Butylene 78 Butylene dibromide 87 Butylene glycol 80, 227 Butyric acid, normal 168 620 INDEX. PAGE Butyric acid, salts of 159 Butyrolactone 530 Butyroue 137 Butyrophenone 424 Cacodyl 218 Cacodyl chloride 218 Cacodyl cyanide 218 Cacodyl oxide 217 Cacodylic acid 218 Caflfeine 610 Calcium carbide 82 Calico-printing 517 Cane-sugar. 274 Capraldehyde 137 Caproic acid 160 Caramel 275 Carbamic acid 301 Carbamide 301 Carbazole 471 Carbinol 89, 103 Carbohydrates 26G Carbolic acid 307, 308, 404 Carbon, detection of 14 Carbon, estimation of 18 Carbon tetrad iloride 177 Carbonyl chloride 177, 302 Carbon yl-group 132 Carboxyl-group 156 Carboxylic acids 156, 428 Carbylamine reaction 176, 207 Carbylamlnes 294 Carius' method of analysis 27 Carvacrol 349, 409 Casein 277 Catechol 410, 480 Catecholearboxylic acid 452 Catechu 410 Celluloid 282 Cellulose 281 Cellulose nitrates 282 Cetyl alcohol 109 Cetyl palmitate , 192 Chloracetanilide 375 Chloracetic acid 166 Chloral 127 Chloral alcoholate 127 Chloral hydrate 128 Chloranil 428 Chloranilines 375 Chlorethane 178 Chlorethylene 77 PAGE Chlorine carrier 166, 352 Chlorine, detection of. 16 Chlorine, estimation of 27 Chlorobenzene 357 Chlorobenzoic acid . .-. 360 Chlorobenzyl chloride 354 Chlorofonn,. 56, 128, 176 .. «-Chlorohydriu 257, 258 /3-Chlorohydrin 257, 258 Chlorohydrins 80, 228, 257 Chloromalonic acid 245 Chloromethane 174 Chloronaphthalenes 462, 463 Chloronitrobenzenes 367, 375 «-Chloropropionic acid 166, 231 /3-Chloropropionic acid 166, 233 Chlorotoluenes 360 Choline .' 512 Chrysoidine 535 Cinchomeronic acid 496 Cinch on a- bark, alkaloids of 506 Cinchonine 506 Cinchoninic acid 506 Cinnamic acid 443 Cinnamic aldehyde 417 Citric acid 251 Citric acid, salts of 252 Closed-chain compounds 332 Coal-tar, distillation of 305, 309 Coca, alkaloids of. 504 Cocaine 504 Codeine 508, 510 Coke 305 Collidines 491 Collodion 282 Colour-base 520 Combustion apparatus 19, 20 Condensation 133 Congo group of dyes 537 Congo-red 468, 537 Coniine 501 Constitution of organic compounds.. 48 Constitutional fonnulse 50 Copper acetylide 83 Cordite 260, 282 Cream of tartar 249 Creosote oil 308 Cresols 308, 408 Crotonaldehyde 126, 263 Crotonic acid 264 Crotonylene 81, 87 Crystallisation 6 INDEX. 621 PAGE Cumene .349 Gumic acid 349 Cyamelide 295 Cyanic acid 295 Cyanides 290 Cyanides, double 291 Cyanogen 285 Cyanogen chloride i. 287 Cyanogen compounds 285 Cyanohydrins 136, 142 Cyanuric acid 287 Cyanurio chloride 287 Oyinene. 349 Dahlia 527 Daturine 603 Decane 67 Dextrin 98, 280 Dextrose 267 Dextrotartario acid 251, 542, 543 Diacetin 256 Diacetylchloroliydrin 258 Diallyl 87 Diallyl tetrabromide : 87 Diamidoazobenzene hydrochloride. , ..536 Diamidoazobenzenes 366, 368, 376 Diainido-compounds 373, 376 Diainidodiphenyl 391 l:4-DianiidonaphthaIene 468 Diarsenic tetrainet^hyl 218 Diastase 98, 277, 280 Diazoaniidobenzene 387 Diazoamido-compounds 386 Diazobenzeue, chloride, 382 ; nitrate, 382 ; sulphate 382 Diazobenzenesulphonic acid 397, 534 Diazo-compounds 381 Diazo-coinpounds, constitution of — 385 Diazopseudocuinene chloride 537 DiazotoUiene chloride 383, 634 Diazoxylene chloride 537 Dibasic acids, electrolysis of 72, 81 Dibenzylamine 381 Dibromanthraquinone 479 Dibromethylbenzene 445 Dibromethylene 84 Dibromobenzenes 330 Dibromohexahydrobenzene 336 Dibromohexamethyleiie 336 Dibromopropionio acid 263 Dibrombpyridine 436 Dibromosuccinic acid 247, 260 PAGE Dicarboxylic acids 234, 436 Dichloracetic acid 166 Dichloracetone, asymmetrical 134 Dichloracetone, symmetrical — 134, 252, 258 Dichloranthracene 475 Dichlorethylene 84 Dichlorobenzene 313 «ot-Diohlorohydrin 252, 267, 268 Bt/3-Diohlorohydriu 257, 258 Dichloronaphtbalene 463 /3-Diohloropropane 131, 142 <»;3-Dichloropropionio acid 268 Dicyanogen 285 Diethyl ketone 137 Diethylamine 208 Dietliylamine, salts of 209 Dietliylnitrosamine 208 Diethylphosphine 214 Diethylphospliine hydriodide 215 Digallic acid 453 Dihexyl Itetone 187 Dihydric phenols '.399, 401, 410 Dihydrobenzene 336 Dihydrobenzene tetrabromide 336 Dihydroxyacetone 272 Dihydroxyanthraquinones 478, 481 Dihydroxyazobeuzene 534 Dihydroxybenzenes 410 Dihydroxybenzoic acids 452 Dihydroxynaphthalenes 469 Dihydroxypbenanthrene 483 Dihydroxyphthalophenone 631 Diliydroxysuccinic acid 247 Di-isoaniyl ether ' 115 Di-isobutyl ether 115 Di-isopropyl 66 Di-isopropyl ether 115 Di-isopropyl ketone 137 Dimethyl carbinol 103, 105 Dimethyl ketone 130, 137 Dimethylacetic acid 159 Diniethylacetylene 87 Dimethylamidoazobenzene 388 Dimethylamidoazobenzene hydro- chloride ^3* Dimethylamidoazobenzenesnl phonic acid '. 538 Dimethylamine 211 Dimethylaniline 370, 378 Dimethylarsine oxide 217 Diinethylbenzidine 391, 638 622 INDEX. PAGE Dimathylcateohol 411 Dimethylethylamine 211 Dimethylethylmethane 546 Diinethylinalonie acid 244 Dimethylphenylenediamiiies — 376, 635, 536, 539 Dimethylpyridines - 491 Dinaphthols 4(17 Diiiifcro-«-naphthol 467, 638 Dinitro-oe-iiaphthol-disulphonicacid, potassium salt of 467 Dinitrobenzene 365, 366 Di-olefines 87, 88 Diphenio acid 482, 483, 484 Dipheaic anhydride 484 Diphenyl, 338, 350, 4S2 ; Icetone, 351, 424 Diplienylapine 371, 379 Diphenyldicarboxylic acid 482 Diphenylethylene 482 DiphenyliodoiiiuiTi hydroxide 360 Diphenyliodonium iodate 360 Diphenylinethaiie 351, 425 Diphenyl-m-tolylmethane 523, 526 Dippel's oil 486 Dipropargyl 87, 314 Dipropyl ether 115 Dipropyl Itetone 137 Dipropylamine 204 Disacryl 262 Distillation 8 Distillation in steam 7 Distillation of wood 90 Ditolyl 482 Dulcitol 265, 270 Dutch liquid 71 Dyes and their application 514 Dynamite 259 Earth-wax 67 Ecgonine 504 Elementaiy analysis 14 Empirical formula 32 Emulsin 288 Enantiomorphous crystals 549 Enzymes 99, 276 Eosin 532 Epiohlorhydrin 268 Brythritol 264 Erythrosin 533 Bsteriflcation 191 Esters 174 Bthaldehyde 122 PAGB Ethane 58, 67, 84 E theiie 71 Etliene glycol 224 Ether Ill Ethereal salts 174 Ethers Ill Ethoxides 95 Ethyl acetate 188 Ethyl acetoaoetate 193 Ethyl acetoacetate, hydrolysis of 197 Ethyl acetylglycollate 230 Ethyl aoetyllactate 282 Ethyl alcohol 94, 107 Ethyl benzenesulphonate 394 Ethyl benzoate 431 Ethyl benzylraalonate 442 Ethyl bromide 179, 181 Ethyl butylacetoaoetate 198 Ethyl carbinol 105 Ethyl carbonate 302 Ethyl chloride 178, 181 Ethyl chloroformate 302 Ethyl copper acetoacetate 195 Ethyl diethylacetoncetate 196 Etliyl dimethylacetoacetate 196 Ethyl dipropylacetoacetate 196 Ethyl ether Ill Ethyl ethylacetoacetate 196 Ethyl ethylmalonate 202 Ethyl etliylmethylacetoacetate 196 Ethyl ethylpropylacetoacetate 198 Ethyl formate 192 Ethyl glycollate 233 Ethyl hydride j 58 Ethyl hydrogen sulphate 74, 185 Ethyl hydroxycrotonate 200 Ethyl iodide 180, 181 Ethyl isocyanate 296 Ethyl isonitrile 294 mthyl isopropylacetoacetate 196 Ethyl lactate 232 Ethyl malonate 201 Ethyl mandelate 454 Ethyl mercaptan 187 Ethyl methylacetoaoetate 196, 198 Ethyl nitrate 182 Ethyl nitrite 183 Ethyl oxalate 239 Ethyl phthalate 438 Ethyl propylacetoacetate 195, 196 Ethyl propylethylmalonate 202 Ethyl propylmalonate 203 INDEX. 623 PAGE Bthyl salicylate 451 Ethyl sodioacetoacetate 194 Ethyl sodiomalonate 202 Ethyl snccinimide 244 Ethyl sulphate 186 Ethyl sulphide 188 Ethylamine 205 Ethylamine, salts of. 208 Bthylates 95 Bthylbenzene 345, 347 Ethylhenzylaniline 522 Bthylcarbylamine 207, 294 Ethylene 71, 79 Ethylene alcohol 224 Ethylene chlorohydrin 227, 228 Ethylene cyanohydrin 234 Ethylene diamine 439 Ethylene dibromide 77 Ethylene dichloride 77 Ethylene glycol 80, 224 Ethylene oxide 228 Ethylene series 71 Bthylenediphthalimide 439 Ethylenelactic acid 234 Ethylidene bromide 142 Ethylidene chloride 142 Ethylidenelactic acid 234 Ethylnialonic acid 244 Etliylphosphine 214 Ethylphosphine hydriodide 215 Ethylphthalimide 439 Ethylpropylacetio acid 203 Ethylpropylmalonic acid 203 Bthylsulphone 188 Bthylsulphonic acid 187 Pats 169 Fatty acids. 145 Fatty acids, electrolysis of 68, 68 Fatty acids, synthesis of, from ethyl acetoacetate 193 Fatty acids, synthesis of, from ethyl malonate 201 Fatty acids, synthesis of, from next higher homologues 205 Fatty acids, synthesis of, from next lower homologues 206 Fatty compounds 332 Pehling's solution 268 Ferment 97 Fermentation, acetic 96, 150 Fermentation, alcoholic 97-100 PAGE Fermentation, butyric 159 Fermentation, diastatic 98, 280 Fermentation, lactic 159 Fittig's reaction. ; 341 Fluorescein, 437, 632 ; reaction.. 411, 437 Formaldehyde 93, 118, 1S7 Formaldoxime 120 Forinamide 165 Formanilide 875 Formic acid 93, 145, 167 Formic acid, salts of 148 ■Formose 122, 272 Formula, calculation of a SO Fractional crystallisation 7 Fractional distillation 11 Friedel and Crafts' reaction 340, 424 Fructose 270 Fructosephenylhydrazone 273 Friictosoxime 272 Fruit-sugar 270 Fuchsine 525 Funiaric acid 247, 658 Fusel oil 98, 100, 106 Galactosazone 270 Galactose 269 Gallic acid 462 Gas liquor 305 Gasoline 70 General formulie 66 Glacial acetic acid 152 Gluconic acid 269 Glucosates 268 Glucosazone 273, 274 Glucose 267 Glucosephenylhydrazone 269, 272 Glueosides 287 Glucosone 274 Glncosoxime 269 Glutario acid 235, 244 Gluten 2S0 Glyceraldehyde 272 Glyceric acid 256 Glycerides 1^^ Glycerin 264 Glycerol 170,172,254 Glycerose ..' 272 Glyceryl acetate 266, 256 Glyceryl trichloride 267 Glyceryl trinitrate 258 Glycine 299 Glycine hydrochloride 300 624 INDEX. PAGE Glycol diacetate 226 Glycol, sodium compounds of. 225 GlycoUic acid 228, 229, 271 GlycoUic aldehyde 22's Glycols 223, 224 Glyoxal. 228, 229, 248 Glyoxylie acid 228 Granulose 279 Grape-sugar 267 Graphic formulae 50 Guaiacol 410 Gum benzoin 430 Gun-cotton 282 Halogen carrier. 166, 352 Halogen derivatives 174, 352 Hard soap 172 Heavy oil 306 Helianthin 536 Hemihedral crystals 543, 549 Hemimellitene 349 Hemlock, alkaloids of. 501 Heptaldehyde 129, 137 Heptane 67 Heptyl alcohol, normal 129 Heptylic acid 129, 160 Hexachloracetone 134 Hexahydrobenzene 335 Hexahydropyridiiie 486, 489 Hexahydrotetrahydroxybenzoic acid.. 505 Hexamethylene 335 Hexamethylpararosaniline chloride . .528 Hexane 65, 67 Hexyl alcohol 265 Hexyliodide 265 Hexylene 79 Hexylic acids 160 Hippuricacid 300, 430 Hofmann's violet 527 Homologous series 66 Hydracrylic acid 231, 233 Hydranthracene 474, 475 Hydrazines 385, 388 Hydrazobenzene 391 HydrazOnes 134, 136, 272, 389 Hydrobenzamide 420 Hydrocarbons, aromatic, oxidation of 429 Hydroeinnamie acid 443 Hydrogen cyanide 287 Hydrogen, detection of '. . . . 15 Hydrogen, estimation of. 18 Hydrolysis 172^ 192 PAGE Hydroquinone 410, 411, 426 Hydroxides, quaternary ammonium . .210 Hydroxides, quaternary arson ium 216 Hydroxides, quaternary phosphonium 215 Hydroximes 134, 212 Hydroxyacetic acid 229, 231 Hydroxyaldehydes, arotnatic 421 Hydroxyanthraquinone 477, 479 Hydroxyazobeuzene 533, 534 Hydroxyazobenzenesulphonic acid ...534 Hydroxybenzaldehydes 422, 423 Hydroxybenzene 404 Hydroxy ben zoic acids ; 450, 451 Hydroxybenzyl alcohols 416, 417 /3-Hydroxy butyric acid 199, 264 y-Hydroxybutyric acid 530 Hydroxycarboxylic acids. . . .142, 231, 446 Hydroxy cyanides 142 Hydroxydicarboxylic acids 245 Hydroxyethyl cyanide 142 Hydroxyethylsulphonic acid 513 Hydroxyethyl tri I nethylammon i urn hydroxide 513 Hydroxyhydroquinone 412, 414 Hydroxyisopropyl cyanide 142 Hydroxylamine 134, 183 Hydroxymalonic acid 245 «-Hydroxypropionic acid 231 /3-Hydroxypropionic acid 231, 233 Hydroxysuccinic acid 245 Hydroxysulphonic acids 140, 408 Hydroxy toluenes 408 Hydroxy tricarboxylic acids 251 y-Hydroxy valeric acid 201 Hyoscine 503 Hyoscyamine 503 Hypnone 424 Indican 539 Indigo-blue, 421, 446, 539 ; carmine, 539 ; dyeing with, 519 ; synthesis of 540 Indigo-vi'hite 519, 539 Indigodisulphonic acid.. 539 Indigotin 539 Indoxyl 540 Indoxylic acid.... 540 Inulin 270 Inverse substitution 57 Inversion 276 Invert sugar 270, 276 Invertase 100, 276 INDEX. 625 paoe: lodacetic acids 166 lodethaiie 180 Iodine, detection of. 16 Iodine, estimation of 27 Iodine green 527, 528 lodobenzene 358 lodobenzene dichloride 359 Iodoform 175 Iodoform reaction 96 lodonitrobenzenes 367 lodosobenzeue 359 lodoxy benzene 359 Isethionic acid 513 Iso-alcohols 104 Isoamyl alcohol 106 Isoamyl isovalerate 193 /3-l8oamylene. . , 78 Isobutaldehyde 137 Isobntane 61, 65, 67 Isobiityl alcohol 104, 106 Isobutyl carbiuol 104 Isobutylene 78 Isobutyric acid 159, 167 Isobutyrone 137 Isoeyanides 294 Iso-hydrocarbons 65 Isomerism-. 64 Isonicotinic acid 492 Isonitriles-. . . .- 294 Isopentane <33 Isophthalic acid 439 Isopropyl alcohol 105, 107, 131 Isopropyl bromide 80 Isopropyl carbinol 104, 106 Isopropyl iodide 181 Isopropyl acetic acid 158 Isopropyl benzene. 349 Isopropylbenzoic acid 349 Tsoqninoline 485, 496 Isosuccinic acid 235, 244 Isothiocyanates, alky] 298 Isovaleraldehyde 137 Isovaleric acid 158, 159, 167 Kerosene 70 Ketones 130, 423 Ketones, condensation of 144 Ketones, oxidation of. 142 Ketoximea 134 K.ieldahVs metliod 27 Komer's method of determining con- stitution 320 Chem. 7/6 ^ Lactic acid 200, 231, 544, 545 Lactic acid, salts of. 232 Lactones 530 Lactose 159, 277 Lakes 480, 518 Lard 170 Laubenheimer's reaction 484 Laudanum..'..'. 508 Laurie acid, 16? Laurone 137 Lead ethyl 223 Le Bel and vau't-Hoflfs theory. 544 Lecithin 512 Leucaniline 523, 526 Leuco-base 520 Leuco-compound .518 Leuco-malacliite green 521 Lenco-pararosaniline 523, 524 Leuco-rosaniline 523, 526 Levotartaric acid 251, 543, 553 Levulinic acid 200 Levulose 270 Liebermann's reaction 209, 462 Light oil 306 Light petroleum 70 Ligroin 70 Lutidines ..491 Magenta 525 Malachite green 521 Maleic acid 247, 558 Maleic anhydride 247, 558 Malic acid 245, 250,-544, 545, 549 Malonic acid 235, 239 Maltosazone 277 Maltose v. 98, 276 Mandelic acid 453 Mannitol 265, 271 Mannose 269 Margaric acid 160 Margarine 173 Marsh-gas S5 Martins' yellow 538 Meconic acid 508 Melissyl alcohol 109 Melting-point 13 MRndius' reaction 205 Mercaptans ■. .187 Mercaptides 1 87 Mercuric ethiodide 222 Mercuric etlmcliloride 222 ATercuric etbohydroxide 223 N 626 INDEX. PAGE Mercuric ethyl 222 Mesityl oxide 183, 134 Mesitylene , . . ..328, 333, 348 Mesitylenio acid 328, 349 Mesotartaric acid 251, 543, 553 Metachloral 128 Meta-coinpounds 322 Metaldehyde 127 Mebanilic acid 397 Methaldehyde 118 Methane 63, 67 Methane series 53, 67 Methene dicliloride 175 Metlioxides 91 ■ Methoxybenzaldehyde 423 Methoxybenzoic acids 409, 452 Methoxybenzyl alcohol 417 Methoxycinchonine 505 Metlioxy-group 498 Methoxyquinoline-y-carboxylic acid. .505 Methyl acetate 193 Methyl alcohol 89, 107 Methyl bromide 177, 181 Methyl butyrate 193 Methyl carbinol 94 Methyl chloride .66, 91, 174, 181 Metliyl cyanide 289, 294 Methyl ether Ill Methyl ethyl ether 115 Methyl hydrogen sulphate 91 Methyl iodide. . , 177, 181 Methyl isonitrile 294 Methyl isophthalate 440 Methyl isopropyl ether 116 Methyl methylsalicylate 449, 451 Methyl nitrate 183 Metliyl nitrite 184 Methyl orange , , , , 536 Methyl oxalate .90, 238 Methyl potassiosalicylate 449 Methyl propionate . , 193 Methyl propyl ether, 116 Methyl salicylate 449, 461 Methyl sulphate 91 Methyl terephthalate 440 Methyiacetainide 136 Methylacetylene 87 Methylal 122 Methylainine 211 Methylaniline 370, 378 Methylated spirit 101 Methylates 91 paqb: Methylbenzene 844 Methyloatechol 410 Methylcinnamic acids 444 Methylcresols 409- Methylene blue 53a Methylene dicliloride 175- Methylenitan 272 Methylethyl 60 Methylethyl carbinol 104, 106 Methylethyl ketone 139' Methylethylacetie acid 158, 160, 545- Metliylethylainine 211 ' Methylethylene 7» Methylisopropyl ketone 137 Methylisopropylbeiizene 349* Methylmorphine 510 Metliylnaphthalenes 462 Methyl phosphine J2]i Methylpiperidine 490 Methylpropyl 61 Methylpropyl ketone 131 Methylpyridijies , 491 Metliylquinoline 49& Methylsalicylic acid 449, 451 Methylsuccinic acid 214 Methylsulphonic acid 184 Methyltheobroiniiie 510 Methyltriphenylmethane 523 Methyl violet 528 Middle oil 306, 807 Milk-sugar 277 Mineral naphtha 69 Mirbane, essence of.. 365 Mixed amines 211 Mixed anhydrides 164 Mixed ethers 115 Mixed ketones 137 Molecular formula 32' Molecular weight, determination of. . 3^ Molecular weight, determination of, by chemical methods 32' Molecular weight, determination of, by physical methods 36 Monacetin 256 Monobroinopyrldine 486 Monocarboxylic acids 157 Monochloracetone 134 Monochloranthracene 475 Monoformin .147, 260 Monohydric alcohols 89 Monohydrio phenols 404 Monohydroxynaphthalenes 466' •INDEX. 627 Monosea 266, 2S3 Uonlanta 616 Morpliiiie, 509 ; inethiodide 609 Mnoio acid 270 Hnstard-oil 298 Myristic acid 167 Uyroain 298 Naphtha, crude, 306 ; solvent 307 Naphthalene 307, 308, 338, 455 Naphthalene, ainido-derivatives of. ..464 Naphthalene, constitution of 466 Naphthalene, derivatives of 462 Naphthalene derivatives, isomerism of 460 Naphthalene, homologues of. 462 Naphthalene, nitro-derivatives of 464 J^^aplithalene picrate 456 Naphthalene, sulphonic acids of. 467 Naphthalene tetrachloride 438, 463 Naphthalene yellow 467 Naphthalene-(K-sulphonic acid 468 Naphthalene-/3-sulphsnic acid 468 27aphthalenedisulphonic acids 468 Naplithalic acid 484 .te-Naphthaquinone 465, 468 ,/S-Naphthaquinone 469 Naphthionic acid 468, 637 -«-Naphthol, 459, 466 ; ^-Naphthol. . ..467 Naphthol yellow 467, 638 -A'NaplitholdisuIphonic acid 538 .^-Naphtholdisulphonic acid 537 ■«'Naphtholmonosulphonic acid 638 Naphtholmonosnlphonic acids 468 Naphthols 466 «-Naphtholtrisulphonic acid 467, 538 ^-Naphthylamine 45S, 465 ^S-Naphthylamine 465 Naphthylaminemonosul phonic acids.. 467 1 :4-Naphthylaminesulphonic acid 468 Narcotine 608 Natural gas 69 Neurine 513 Nicotine, 502 ; dimethiodide 502 Nicotinic acid 485, 492, 502 ITightshade, alkaloids of 503 Nitracetanilides 375 Nitranilines 375 Nitrates, ethereal. 182 Nitrates of cellulose 282 Nitriles 136, 293 Nitrites, ethereal 183 I Nitroalizarln 481 Nitrobenzaldehydes 420 Nitrobenzene 365 Nitrobenzoic acids ...'.'.'. 435 Nitroe.ijnianiic acids 445 Nitro-compoands ....;: 334, 362 Nitroethane 184 Nitrogen,- detection of. 15 Nitrogen, estimatiicm of .■..'.■.■.■ 23 Nitroglycerin ; ; 258 Nitrometer, Schiff's;.; 24 /3-Nitro-«-naphthylamine 464 «-Nitronaphtlialene.'. .'.'. 458, 464 /3-Nitroiraplithalene. ; ; ; 464 Nitroparaffins 184 Nitrophenols. . . ..::::; 405 Nitrophenyldibromopropionic acids . . 445 Nitrophenylpropiolicacid 445 Nitrophthalic acid-. .■.■.■ 467 Nitrosamines 209, 377 Nitrosobenzene ■.-,; 369 Nitrosodimethylaniline; ; . . ; 378, 539 Nitrosomethylaniline .:;;:: 378 Nitrosophenol 379 Nitrosopiperidine - 490 Nitro toluenes - 367 Nonane ; . ; 67 Normal alcohols ....:;... 104 Nonnal butylene -.'.-. 78 Nonnal hydrocarbons 66 Nux vomica, alkaloids of 606 Octacetylmaltose - 277 Octacetylsucrose 276 Octane 67 CEnanthol 129, 137 (Enanthone 137 Oil of, aniseed, 423, 452; bitter almonds, 418; garlic, 262; mus- tard, 298 ; wintergreen 89, 450 Oils. .169 Oleflant gas 71 defines ^ 71 Oleic acid 171, 264 Oleomargarine ;-.::; 173 Open-chain compounds-.-. -.ir-..-; 332 Opium, 608 ; alkaloids of.-. 508 Optical isomerides .- j 548 Optically active substances. -. ; 641 Organic acids, ethereal salts of 188 Organic compounds, classification of.: 331 628 INDEX. PAGE Organo-metallio compounds 220 Ortho-compouiids 322 Orthoquiiioiies 469 Osazoiies ' 273 OSOIIBS '. .'. 273 Oxalic acid f.--235 Oxalic acid, salts of 236 Oxamide 239 Oxainines 215 Oxanilide 377 Oxanthrol '..'. 477 Oxidising agents 92 Oxiines 134, 212 Ozokerite. 67, 70 Palmitic acid . . . . ; 160, 167 Palmitoue 137 Papaverine 508 Paracetaldehyde 126, 143 Para-compounds 322 Paracyanogen 286 Paraffins.... 53, 66, 67 Paraffin-wax 66 Paraformaldehyde 120 Paralactic acid 233 Paraldehyde .126 Paraleucaniliue 623, 524 Paraquinones 469 Pararosaniline 523 Parchment paper 231 Pentamethylene diamine j . . .491 Pentane 63, 67 Pentylene 78 Pepper, alkaloid of 503 Perchloracetone 134 Peri-position 461 Perlcin's reaction 444 Peru balsam 430 Petroleum 69 Petroleum ether , 70 Fhenanthraquinone 483 Phenanthraquinone, bisulphite com- pound of 483 Fhenanthraquinone dioxime 483 Fhenanthrene 308, 474, 481 Phenetole 405 Phenol 307, 404 Phenolphthalein 531 Phenols 398 Phenolsulphonic acids 397, 408 Phenyl, bromide, 858 ; chloride, 867 ; cyanide, 433; ethyl ether, 405; / PAGE. group, 338 ; iodide, 368 ; methyl ether, 405 ; radicle 344, 40* Plienylacetalileliyde 405, 417 Plienylacetic acid 442 Phenylacetonitrile 434, 442 Pli'enylacetylene 445 Phenylaerylic acid 441, 443 Phenylamine ." 373 Phenyl-/3-broniopFopionic acid 444 Phenylbutyleiie, 459; dibromide 459 Phenylbutyric acid 441 Phenylcarbijiol .»415 Phenylcarbylamine 176, 372, 374 Phenylchloroform 362 Phenyl-fl6j3-dibromopropionic acid 444 Phenylene radicle 344, 403 Fhenylenediamines 373, 376, 426, 53& Fhenylethane 347 Fhenyletliyl alcohol 417 Fhenylethylene 443. Fhenylforniic acid 441 Phenylglycine '. 540 Phenylglycinecarboxylie acid 64» Fhenylglycollio acid 45S Fhenylhydrazine 388 Phenylhydrazones 134, 272, 389- Fhenylhydroxylamine 369' Phenylisocroionic acid 444, 459' Phenylisocyanide 176 Phenylmaltosazone 277 Phenylmethane 344 Phenylmethyl, carbinol, 424 ; ketone.428 Phenylmethylacrylic acid 444 Phenylmethylpyrazolono 511 Phenylpropiolic acid 441, 445 Phenylpropionie acid 441, 44& Phenyltrimethylammonium Iodide . . .372 Phloroglucinol 413, 413' Phloroglucinol triacetate.^^ A1S Phloroglucinol trioxim&:\y 418- Phorone 133, 134 Phosphines 214 Phcsphomolybdic acid 501 Phosphorus, detection of 18 Phosphorus, estimation of. 39' Phosphotungstic'acid 501 Fhotogene 70 Phthaleins 630 Phthalic acid 436, 466 Phthalic acids 327, 436 Phthalic anhydride 439, 476, 540 Phthalimlde 439, S4ft INDEX. 629 PAGE Phthalophenone 530 Phtlialyl chloride 438 Physical isoiuerldes 548, 558 Picolines 491 Picolinic acid 492 Picric acid , 406, 501, 514 Pinacoline 141 Pinacones . 141 Piperio acid 490, 503 Piperidine 486, 489 Piperine 490, 603 Pitch 303 Polariineter 268 Polyhydric alcohols. . , 262 Polymerisation 121 Polyoses 278, 283 Ponceau SR 537 Ponceaux 537 Potassium, acetylide, 84; cresate, 403 ; diphenylamine, 379 ; phenate, 405 ; phthalimide, 439 ; picrate ... .407 Potassium fevricyanide 293 Potassium ferrocyanide 292 Potassium myrouate 298 Primary alcohols 104 Primary hydrocarbons 65 Primula B27 Proof-spirit 102 Propaldehyde 106, 129, 137 Propane 60, 67 Propenyl acetate , 255 Propenyl alcohol 254 Propenyl chlorohydrin 257 Propenyl dichlorohydrin 257 Propenyl iodide 261 Propenyl tribromide 254 Propenyl trichloride .257 Propenyl trinitrate 258 -— —ECDpionamide 206 Propione 137 Propionic acid 105, 158, 167 Propionic acid, salts of 158 Propionitrlle 294 Propionyl chloride 162 Propiophenone 424 Propyl alcohol 105, 107 Propyl bromide 180 Propyl carbinol 104 Propyl formate 193 Propyl hydride 60 Propyl iodide 181 Propylacetic acid 158 Propylamine 204, 211 Propylene , 7s Propylene chlorohydrin 228 Propylene dibromide 78, 254 «/3-Propylene glycol : . . .227, 231 Bty-Propylene glycol 23S Propylene oxide 228 Propylmalonic acid 205 «-Propylpiperidine, d 602 Protoeatechuic acid 462 Prussian blue 293 Prussic acid 287 Pseudocnmene 349 Purification of compounds 4 Purpurin 478, 481 Pyridine, 307, 338, 484, 485; alka- loids derived from, 501 ; deriva- tives, isomerism of, 488 ; horao- logues of, 491 ; methiodide 486 Pyridine-«^-dicarboxylic acid 492 Pyridine-^-carboxylic acid 502 Pyridine-zSy-dicarboxylic acid 496 Pyridiuecarboxylic acids «, j8, y . . 491, 492 Pyrocatechol 410 Pyrogallic acid, Pyrogallol 412 Pyrogallolcarboxylic acid 462 Pyrogalloldimethyl ether 418 Pyroligneous acid 150 Pyrotartaric acid 244 Pyrnvio acid 200, 233 Pyruvic acid hydrazone,. 200 Qualitative elementary analysis 14 Quantitative elementary analysis 18 Quinic acid 505 Quinine, 504 ; dimethiodide 505 Qulninic acid 505 Quiiiol 411 Quinoline, 338, 484, 493; alkaloids derived from, 504; j-carboxylic acid, 506; methiodide 494 Quinolinic acid, 492 ; anhydride 49S Quinone *25 Quinone chlorimides 42S Quinone dichlorodiiraides 428 Quinonedioxime 426 Quinonemonoxime 426 Quinones 425 Racemic acid 248, 251, 542, 554 Racemic compound 549 Bacemic compounds, res.olution of. . .656 630 IXDEX. PAGE Badiclea 116, 343 Babional formulse 50 Reducing agents 55 Refined petroleum 70 Refined spirit 101 Reiiner's reaction 421, 448 Resorcin yellow 536 Resorcinol 410, 411 Resorcylic acids 448 Rhodonates 297 Bocellin -. 537 Boohelle salt 249 Bosaniline 523, 625 Rosolic acid 530 Ruberythric acid ■ -. .- 478 Saccharic acid 269 Saccharimeter 268 Saccharin 435 Saccharosates 276 Saccharose 274 Salicin 416 Salicyl alcohol 416 Salicylaldeliyde 422 Salicylic acid, 450 ; salts of 451 Saligenin, 416, 421 ; methyl ether 417 Sandineyer's reaction... 357, 858, 384, 434 Saponification 172 Sansolactic acid 133, 544, 545 Satnrated compounds....- ,. ,. 58 Scarlet E 637 ScliifF's, or the rosaniline reaction . , .124 Schweinfurter green 153 Schweitzer's reagent 281 Sealed tubes .- ; 28 Secondary alcohols 104 Secondary aromatic bases 496 Secondary hydrocarbons 65 Seminin 269 Sepaipation of coinpounds 4 Side-cliains 337 Silicon, organic compounds of. 218 Silicon tetramethyl 219 Silicon tetrethyl 219 Silicononane 219 Silicononyl acetate 219 Silicononyl alcohol 219 Silicononyl chloride 219 Silver acetylide 84 Silver theobromine 511 Skraup's reaction 493 Soaps 169 pjiob Sodium ammonium racemate. S57 Sodium glycerol 256 Sodium hydroxyethylsnlphonate 140 Sodium hydroxyisopropylsulphonate..l40 Sodium phenylcarbouate 447, 450 Sodium picrate 407 Soft soap 172 Solar oil 70 Sorbitol 265, 269, 271 Spirit of wine 94 Spirits, manufacture of . , . , lOO Stannic ethyl 223 Stannous ethyl. 223 Starch 278 Starch cellulose. . , 279 Stearic acid , 160, 167 Stearin! 172 Stearone 137, 139 Stereo-chemical isomerides 558 Stereo-isomerism 558 Stibines 216 Stilbene,"482 ; dibromide 482 Storax 418, 443 Strontium sucrosate 276 Strychnine, 506 ; methiodide 507 Styrolene 445 Substitution. . ; 57 Substitution, rule of 364 Succinamide 243 Succinic acid .'.-.■..- 240 Succinic acid, electrolysis of. 72, 76 Succinic acid, salts of 241 Succinic anhydride 241 Succinimide 243 Succinimide, metallic derivatives of. .243 Succinyl chloride 242 Sucrosates 276 Sucrose ; 274 Sugars 266 Sugars, hydrazones 6f.> ■.-.-.; 272 Sulphanilic acid... ... -. 396 Sulphates, «ther«al 185 Sniphides 186 Sniphocyanicacid.. 296 Sulphonal 188 Sulphonamides.... 894 Sulphonation 893 Sulphones 188 Sulphonic, acids, 187, 334, 392; chlorides 394 Sulphovinic acid 185 Sulphur, detection of 18 INDEX. 