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cathode.

2. Cupellation. When the gold is alloyed with easily oxidizable metals, such as copper or lead, it may be refined by cupellation. The alloy is fused with an oxidizing flame on a shallow hearth made of bone ash, which substance has the property of absorbing metallic oxides but not the gold. Any silver which may be present remains alloyed with the gold.

3. Parting with sulphuric acid. Gold may be separated from silver, as well as from many other metals, by heating the alloy with concentrated sulphuric acid. This dissolves the silver, while the gold is not attacked.

Physical properties. Gold is a very heavy bright yellow metal, exceedingly malleable and ductile, and a good conductor of electricity. It is quite soft and is usually alloyed with copper or silver to give it the hardness required for most practical uses. The degree of fineness is expressed in terms of carats, pure gold being twenty-four carats; the gold used for jewelry is usually eighteen carats, eighteen parts being gold and six parts copper or silver. Gold coinage is 90% gold and 10% copper.

Chemical properties. Gold is not attacked by any one of the common acids; aqua regia easily dissolves it, forming gold chloride (AuCl3), which in turn combines with hydrochloric acid to form chlorauric acid (HAuCl4). Fused alkalis also attack it. Most oxidizing agents are without action upon it, and in general it is not an active element.

Compounds. The compounds of gold, though numerous and varied in character, are of comparatively little importance and need not be described in detail. The element forms two series of salts in which it acts as a metal: in the aurous series the gold is univalent, the chloride having the formula AuCl; in the auric series it is trivalent, auric chloride having the formula AuCl3. Gold also acts as an acid-forming element, forming such compounds as potassium aurate (KAuO2). Its compounds are very easily decomposed, however, metallic gold separating from them.

EXERCISES

1. From the method of preparation of platinum, what metal is likely to be alloyed with it?

2. The "platinum chloride" of the laboratory is made by dissolving platinum in aqua regia. What is the compound?

3. How would you expect potassium aurate and platinate to be formed? What precautions would this suggest in the use of platinum vessels?

4. Why must gold ores be roasted in the chlorination process?

CHAPTER XXXII SOME SIMPLE ORGANIC COMPOUNDS

Division of chemistry into organic and inorganic. Chemistry is usually divided into two great divisions,—organic and inorganic. The original significance of these terms was entirely different from the meaning which they have at the present time.

1. Original significance. The division into organic and inorganic was originally made because it was believed that those substances which constitute the essential parts of living organisms were built up under the influence of the life force of the organism. Such substances, therefore, should be regarded as different from those compounds prepared in the laboratory or formed from the inorganic or mineral constituents of the earth. In accordance with this view organic chemistry included those substances formed by living organisms. Inorganic chemistry, on the other hand, included all substances formed from the mineral portions of the earth.

In 1828 the German chemist Wöhler prepared urea, a typical organic compound, from inorganic materials. The synthesis of other so-called organic compounds followed, and at present it is known that the same chemical laws apply to all substances whether formed in the living organism or prepared in the laboratory from inorganic constituents. The terms "organic" and "inorganic" have therefore lost their original significance.

2. Present significance. The great majority of the compounds found in living organisms contain carbon, and the term "organic chemistry," as used at present, includes not only these compounds but all compounds of carbon. Organic chemistry has become, therefore, the chemistry of the compounds of carbon, all other substances being treated under the head of inorganic chemistry. This separation of the compounds of carbon into a group by themselves is made almost necessary by their great number, over one hundred thousand having been recorded. For convenience some of the simpler carbon compounds, such as the oxides and the carbonates, are usually discussed in inorganic chemistry.

The grouping of compounds in classes. The study of organic chemistry is much simplified by the fact that the large number of bodies included in this field may be grouped in classes of similar compounds. It thus becomes possible to study the properties of each class as a whole, in much the same way as we study a group of elements. The most important of these classes are the hydrocarbons, the alcohols, the aldehydes, the acids, the ethereal salts, the ethers, the ketones, the organic bases, and the carbohydrates. A few members of each of these classes will now be discussed briefly.

THE HYDROCARBONS

Carbon and hydrogen combine to form a large number of compounds. These compounds are known collectively as the hydrocarbons. They may be divided into a number of groups or series, each being named from its first member. Some of the groups are as follows:

METHANE SERIES CH4 methane C2H6 ethane C3H8 propane C4H10 butane C5H12 pentane C6H14 hexane C7H16 heptane C8H18 octane ETHYLENE SERIES C2H4 ethylene C3H6 propylene C4H8 butylene BENZENE SERIES C6H6 benzene C7H8 toluene C8H10 xylene ACETYLENE SERIES C2H2 acetylene C3H4 allylene

Only the lower members (that is, those which contain a small number of carbon atoms) of the above groups are given. The methane series is the most extensive, all of the compounds up to C24H50 being known.

It will be noticed that the successive members of each of the above series differ by the group of atoms (CH2). Such a series is called an homologous series. In general, it may be stated that the members of an homologous series show a regular gradation in most physical properties and are similar in chemical properties. Thus in the methane group the first four members are gases at ordinary temperatures; those containing from five to sixteen carbon atoms are liquids, the boiling points of which increase with the number of carbon atoms present. Those containing more than sixteen carbon atoms are solids.

Sources of the hydrocarbons. There are two chief sources of the hydrocarbons, namely, (1) crude petroleum and (2) coal tar.

1. Crude petroleum. This is a liquid pumped from wells driven into the earth in certain localities. Pennsylvania, Ohio, Kansas, California, and Texas are the chief oil-producing regions in the United States. The crude petroleum consists largely of liquid hydrocarbons in which are dissolved both gaseous and solid hydrocarbons. Before being used it must be refined. In this process the petroleum is run into large iron stills and subjected to fractional distillation. The various hydrocarbons distill over in the general order of their boiling points. The distillates which collect between certain limits of temperature are kept separate and serve for different uses; they are further purified, generally by washing with sulphuric acid, then with an alkali, and finally with water. Among the products obtained from crude petroleum in this way are the naphthas, including benzine and gasoline, kerosene or coal oil, lubricating oils, vaseline, and paraffin. None of these products are definite chemical compounds, but each consists of a mixture of hydrocarbons, the boiling points of which lie within certain limits.

2. Coal tar. This product is obtained in the manufacture of coal gas, as already explained. It is a complex mixture and is refined by the same general method used in refining crude petroleum. The principal hydrocarbons obtained from the coal tar are benzene, toluene, naphthalene, and anthracene. In addition to the hydrocarbons, coal tar contains many other compounds, such as carbolic acid and aniline.

Properties of the hydrocarbons. The lower members of the first two series of hydrocarbons mentioned are all gases; the succeeding members are liquids. In some series, as the methane series, the higher members are solids. The preparation and properties of methane and acetylene have been discussed in a previous chapter. Ethylene is present in small quantities in coal gas and may be obtained in the laboratory by treating alcohol (C2H6O) with sulphuric acid:

C2H6O = C2H4 + H2O.

Benzene, the first member of the benzene series, is a liquid boiling at 80°.

The hydrocarbons serve as the materials from which a large number of compounds can be prepared; indeed, it has been proposed to call organic chemistry the chemistry of the hydrocarbon derivatives.

Substitution products of the hydrocarbons. As a rule, at least a part of the hydrogen in any hydrocarbon can be displaced by an equivalent amount of certain elements or groups of elements. Thus the compounds CH3Cl, CH2Cl2, CHCl3, CCl4 can be obtained from methane by treatment with chlorine. Such compounds are called substitution products.

Chloroform (CHCl3). This can be made by treating methane with chlorine, as just indicated, although a much easier method consists in treating alcohol or acetone (which see) with bleaching powder. Chloroform is a heavy liquid having a pleasant odor and a sweetish taste. It is largely used as a solvent and as an anæsthetic in surgery.

Iodoform (CHI3). This is a yellow crystalline solid obtained by treating alcohol with iodine and an alkali. It has a characteristic odor and is used as an antiseptic.

ALCOHOLS

When such a compound as CH3Cl is treated with silver hydroxide the reaction expressed by the following equation takes place:

CH3Cl + AgOH = CH3OH + AgCl.

Similarly C2H5Cl will give C2H5OH and AgCl. The compounds CH3OH and C2H5OH so obtained belong to the class of substances known as alcohols. From their formulas it will be seen that they may be regarded as derived from hydrocarbons by substituting the hydroxyl group (OH) for hydrogen. Thus the alcohol CH3OH may be regarded as derived from methane (CH4) by substituting the group OH for one atom of hydrogen. A great many alcohols are known, and, like the hydrocarbons, they may be grouped into series. The relation between the first three members of the methane series and the corresponding alcohols is shown in the following table:

CH4 (methane) CH3OH (methyl alcohol). C2H6 (ethane) C2H5OH (ethyl alcohol). C3H8 (propane) C3H7OH (propyl alcohol).

Methyl alcohol (wood alcohol) (CH3OH). When wood is placed in an air-tight retort and heated, a number of compounds are evolved, the most important of which are the three liquids, methyl alcohol, acetic acid, and acetone. Methyl alcohol is obtained entirely from this source, and on this account is commonly called wood alcohol. It is a colorless liquid which has a density of 0.79 and boils at 67°. It burns with an almost colorless flame and is sometimes used for heating purposes, in place of the more expensive ethyl alcohol. It is a good solvent for organic substances and is used especially as a solvent in the manufacture of varnishes. It is very poisonous.

Ethyl alcohol (common alcohol) (C2H5OH). 1. Preparation. This compound may be prepared from glucose (C6H12O6), a sugar easily obtained from starch. If some baker's yeast is added to a solution of glucose and the temperature is maintained at about 30°, bubbles of gas are soon evolved, showing that a change is taking place. The yeast contains a large number of minute organized bodies, which are really forms of plant life. The plant grows in the glucose solution, and in so doing secretes a substance known as zymase, which breaks down the glucose in accordance with the following equation:

C6H12O6 = 2C2H5OH + 2CO2.

Laboratory preparation of alcohol. The formation of alcohol and carbon dioxide from glucose may be shown as follows: About 100 g. of glucose are dissolved in a liter of water in flask A (Fig. 90). This flask is connected with the bottle B, which is partially filled with limewater. The tube C contains solid sodium hydroxide. A little baker's yeast is now

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