acid obtained by heating the anhydride of the trans-acid, forms prisms which melt at 192° C. When heated with hydrochloric acid it passes into the trans-variety. The racemic trans-acid is produced by the reduction of the dihydrobromide of '-tetrahydrophthalic acid or A dihydrophthalic acid. It is split into its active components by means of its quinine salt (A. Werner and H. E. Conrad, Ber., 1899, 32, p. 3046). Hexahydroisophthalic acids (cyclo-hexane-1-3dicarboxylic acids) are obtained by the action of methylene iodide on disodio-pentane tetracarboxylic ester (W. H. Perkin, Journ. Chem. Soc., 1891, 59, p. 798); by the action of trimethylene bromide on disodio-propane tetracarboxylic ester; and by the reduction of isophthalic acid with sodium amalgam, the tetrahydro acids first formed being converted into hydrobromides and further reduced (A. v. Baeyer and V. Villiger, Ann., 1893, 276, p. 255). The cisand trans- forms can be separated by means of their sodium salts. The trans-acid is a racemic compound, which on heating with acetyl chloride gives the anhydride of the cis-acid.

Hexahydroterephthalic acids (cyclo-hexane-1·4-dicarboxylic acids). These acids are obtained by the reduction of the hydrobromides of the di- and tetra-hydroterephthalic acids or by the action of ethylene dibromide on disodio-butane tetracarboxylic acid. An important derivative is succino-succinic acid, CH2O2(CO2H)2, or cyclo-hexanedione-2-5-dicarboxylic acid-1-4, which is obtained as its ester by the action of sodium or sodium ethylate on succinic ester (H. Fehling, Ann., 1844, 49, p. 192; F. Hermann, Ann., 1882, 211, p. 306). It crystallizes in needles or prisms, and dissolves in alcohol to form a bright blue fluorescent liquid, which on the addition of ferric chloride becomes cherry red. The acid on heating loses CO, and gives cyclo-hexanedione-1.4.

with acetic anhydride. When boiled with caustic soda it isomerizes to a mixture of the 44 and 4 dihydrophthalic acids. The acid is obtained by boiling the dihydrobromide of the acid with alcoholic potash or by continued boiling of the acid with caustic soda. The acid is formed when phthalic acid is reduced in the cold by sodium amalgam or by heating the 44 and 4 acids with caustic soda. The trans-modification of A acid is produced when phthalic acid is reduced by sodium amalgam in the presence of acetic acid. When heated for some time with acetic anhydride it changes to the cis-form. The trans-acid has been resolved by means of its strychnine salts into two optically active isomerides, both of which readily pass to A dihydrophthalic acid (A. Neville, Journ. Chem. Soc., 1906, 89, p. 1744).

Of the dihydroterephthalic acids, the A1 acid is obtained by heating the dibromide of the tetrahydro acid with alcoholic potash. It cannot be prepared by a direct reduction of terephthalic acid. On warming with caustic soda it is converted into the acid. The acid is also obtained by the direct reduction of terephthalic acid. It is the most stable of the dihydro acids. The A acid is obtained by boiling the cis- and trans-A acids with water, which are obtained on reducing terephthalic acid with sodium amalgam in faintly alkaline solution. The relationships existing between the various hydrophthalic acids may be shown as follows:

A? and A TETRAHYDRO← Heat

AL TETRAHYDRO

Hydrobromide on reduction HEXAHYDRO

Sodium amalgam

A2.5 DIHYDRO

Boil with water

A1.5 DIHYDRO

A 1-4 DIBYDRO

Tetrahydrobenzoic acid (cyclo-hexene1-carboxylic acid-1), CH, CO2H. Three structural isomers are possible. The Aacid results on boiling the 4 acid with alkalis, or on eliminating hydrobromic acid from 1-brom-cyclo-hexanecarboxylic acid-1. The 4 acid is formed on the reduction of benzoic acid with sodium amalgam. The acid is obtained by eliminating the elements of water from 4-oxy-cyclo-hexane-1-carboxylic acid (W. H. Perkin, jun., Journ. Chem. Soc., 1904, 85. p. 431). Shikimic acid (3-4-6-trioxy-4-tetrahydrobenzoic acid) is found in the fruit of Illicium religiosum. On fusion with alkalis it yields para-oxybenzoic acid, and nascent hydrogen reduces it to hydroshikimic acid. Sedanolic acid, C12H2O3, which is found along with sedanonic acid, C12H9O3, in the higher boiling fractions of celery oil, is an orthooxyamyl-A-tetrahydrobenzoic acid, sedanonic acid being orthovaleryl-A-tetrahydrobenzoic acid (G. Ciamician and P. Silber, Ber., 1897, 30, pp. 492, 501, 1419 seq.). Sedanolic acid readily decomposes into water and its lactone sedanolid, CHO2, the odorous constituent of celery oil.

Tetrahydrophthalic acids (cyclohexene dicarboxylic acids). CH(CO2H)2. Of the ortho-series four acids are known. The acid is obtained as its anhydride by heating the acid to 220° C., or by distilling hydropyromellitic acid. Alkaline potassium permanganate oxidizes it to adipic acid. The A2 acid is formed along with the acid by reducing phthalic acid with sodium amalgam in hot solutions. The acid exists in cis- and transforms. The trans-variety is produced by reducing phthalic acid, and the cis-acid by reducing 4 dihydrophthalic acid.

In the meta-series, four acids are also known. The 2 acid is formed along with the (cis) acid by reducing isophthalic acid. The trans acid is formed by heating the cis-acid with hydrochloric acid under pressure. The acid is formed when the anhydride of tetrahydro rimesic acid is distilled (W. H. Perkin, junr., Journ. Chem. Soc., 1905, 87, p. 293).

Sodium amalgam (hot)

A1 TETRAHYDRO

Пlydrobromide on reduction

Remove HBr from dibromide

HEXAHYDRO

Cyclo-heptane Group.

Cyclo-heptane (suberane), CH, obtained by the reduction of suberyl iodide, is a liquid which boils at 117° C. On treatment with bromine in the presence of aluminium bromide it gives chiefly pentabromtoluene. When heated with hydriodic acid to 230° C. it gives methylhexamethylene. On oxidation with nitric acid (sp. gr. 1-4) it yields pimelic acid. Disuberyl, CH13 CH13, a thick oily liquid, boiling at 290–291° C., is obtained by the reduction of suberyl bromide.

Cyclo-heptene, C,H12, is obtained by the action of alcoholic potash on suberyl iodide; and from cyclo-heptane carboxylic acid, the amide of which by the action of sodium hypobromite is converted into cyclo-heptanamine, which, in its turn, is destructively methylated (R. Willstätter, Ber., 1901, 34, 131). Cyclo-heptadiene 1-3, CH10. is obtained from cyclo-heptene (Willstätter, loc. cit.). It is identical with the hydrotropilidine, which results by the destructive methyla tion of tropane.

Cyclo-heptanone (suberone). CHO, is formed on the distillation of suberic acid with lime, and from a-brom-cyclo-heptane carboxylic acid by treatment with baryta and subsequent distillation over lead peroxide (K. Willstätter, Ber., 1898, 31, p. 2507). It is a colourless liquid having a peppermint odour, and boiling at 178.5-179.5° C. Nitric acid oxidizes it to n-pimelic acid.

Tropilene, CHO, is obtained in small quantities by the distillation of a-methyltropine methyl hydroxide, and by the hydrolysis of Bmethyltropidine with dilute hydrochloric acid. It is an oily liquid, with an odour resembling that of benzaldehyde. It forms a benzal compound, and gives an oyxmethylene derivative and cannot be oxidized to an acid, reactions which point to it being a ketone containing the grouping -CH-CO-. It is thus to be regarded as a cyclo-heptene-1-one-7.

Cyclo-heptane carboxylic acid (suberanic acid), CHCO2H, is obtained by the reduction of cyclo-heptene-1-carboxylic acid; from brom-cyclo-heptane by the Grignard reaction; and by the reduction of hydrotropilidine carboxylic acid by sodium in alcoholic solution (R. Willstätter, Ber., 1898, 31. p. 2504). The corresponding oxyacid is obtained by the hydrolysis of the nitrile, which is formed by the addition of hydrocyanic acid to suberone (A. Spiegel, dnn., 1882, 211, p. 117).

Four cyclo-heptene carboxylic acids are known. Cyclo-heptene-1carboxylic acid-1 is prepared from oxysuberanic acid. This acid when heated with concentrated hydrochloric acid to 120-130° C. yields a chlor-acid, which on warming with alcoholic potash is transformed into the cyclo-heptene compound. Cyclo-heptene-2-carboxylic acid-1 is formed by the reduction of cyclo-heptatriene 2-4 6-carboxylic acid-1. On boiling with caustic soda it isomerizes to the corresponding 1-acid.

CH, CH-CH, CH; CH-CH, CH, CH:CH
CH,NMe CH,CH,HO NMeCH,CH, ČH
CH2 CH=CH ĊH2- CH=CH CH, CH, CH
A-'des-methyl
cyclo-octadiene

-

granatanine Cyclo-octadiene, CH, as above prepared, is a strong-smelling oil which decolorizes potassium permanganate solution instantaneously. It readily polymerizes to a di-cyclo-octadiene and polymer (CH2) (R. Willstätter, Ber., 1905, 38, pp. 1975, 1984; G. Ciamician and P. Silber, Ber., 1893, 26, p. 2750; A. Piccinini, Gaza., 1902, 32, 1 p. 260). B-cyclo-octadiene has been prepared from methyl granatinine iod methylate. Cyclo-octane, CHis is obtained by the reduction of the above unsaturated hydrocarbon by the Sabatier and Senderens's method. It is a liquid which boils at 146-3-148° C. and possesses a strong camphor odour. On oxidation it yields suberic acid (R. Willstätter, Ber., 1907, 40, pp. 957). O. Doebner (Ber., 1902, 35, pp. 2129, 2538; 1903, 36, p. 4318) obtained compounds, which in all probability are cyclo-octadienes, by the distillation of B-vinylacrylic acid, sorbic acid, and cinnamenyl acrylic acid with anhydrous baryta. Cyclo-nonane Group.

According to N. Zelinsky (Ber., 1907, 40, p. 780) cyclononanone, CHO, a liquid boiling at 95-97° C., is formed on distilling sebacic acid with lime, and from this, by reduction to the corresponding

The a-acid (a-isophenylacetic acid) is obtained by the hydrolysis of pseudophenylacetamide, formed by condensing diazoacetic ester with benzene, the resulting pseudophenyl acetic ester being then left in contact with strong ammonia for a long time. B-Isophenylacetic acid is formed by strongly heating pseudophenylacetic ester in an air-free scaled tube and hydrolysing the resulting 8-isophenylacetic ester. y-Isophenylacetic acid is obtained by heating the 8 and 8 acids for a long time with alcoholic potash (A. Einhorn, Ber., 1894. 27, p. 2828; E. Buchner, Ber., 1898, 31, p. 2249). 8-Isophenylacetic acid is obtained by heating the iodmethylate of anhydroecgonine ester with dilute caustic soda (A. Einhorn, Ber., 1893, 26, P. 329). Numerous amino-derivatives of the cyclo-heptane series have been prepared by R. Willstätter in the course of his investigations on the constitution of tropine (q.v.). Amino-cyclo-heptane (suberylamine) is obtained by the reduction of suberone oxime or by the action of sodium hypobromite on the amide of cycloheptane carboxylic acid. Cyclo-octane Group.

Few members of this group are known. By the distillation of the calcium salt of azelaic acid H. Mayer (Ann., 1893. 275. p. 363) obtained azelain ketone, C,HO, a liquid of peppermint odour. It boils at 90-91° C. (23 mm.) and is readily oxidized by potassium permanganate to oxysuberic acid. It is apparently cyclo-octanone (see also W. Miller and A. Tschitschkin, Centralblatt, 1899, 2., p. 181).

Pseudopelletierine (methyl granatonine), C,H,NO, an alkaloid of the pomegranate, is a derivative of cyclo-octane, and resembles tropine in that it contains a nitrogen bridge between two carbon atoms. It is an inactive base, and also has ketonic properties. On oxidation it yields methyl granatic ester, which, by the exhaustive methylation process, is converted into homopiperylene dicarboxylic ester, HOC CH CH CH, CH2 CH CH COH, from which suberic acid may be obtained on reduction. When reduced in alcoholic solution by means of sodium amalgam it yields methyl granatoline, CHOH NCH; this substance, on oxidation with cold potassium permanganate, is converted into granatoline, CH, NO, which on distillation over zinc dust yields pyridine. Methyl granatoline on treatment with hydriodic acid and red phosphorus, followed by caustic potash, yields methyl granatinine, CH1sN, which when heated with hydriodic acid and phosphorus to 240° C. is converted into methyl granatanine, CHNCH2, and granatanine, CH, NH. The hydrochloride of the latter base when distilled over zinc dust yields a-propyl pyridine. By the electrolytic reduction of pseudopellet ierine, N-methyl granatanine is obtained, and this by exhaustive methylation is converted into Ades-dimethyl granatanine. This latter compound readily forms an iodmethylate, which on treatment with silver oxide yields the corresponding ammonium hydroxide. The ammonium hydroxide on distillation decomposes into trimethylamine, water and cyclo-octadiene 1·3.

CH, CH-CH, CH, CH-CH, CH-CH-CH, CHINME COCH,NMe CH, →CH2HO·ÑMĚCH,→ CH, CH-CH, CH, CH-CH, CH-CH-CH, Pseudopelletierine N-methyl

granatanine

subsequent reduction of this with zinc, cyclo-nonane, C,His, a liquid boiling at 170-172° C. is obtained.

POLYNESIA, (Gr. woλús, many, and vĥoos, island), a term sometimes used to cover the whole of the oceanic islands in the central and western Pacific, but properly for the eastern of the three great divisions of these islands. The chief groups thus included are Hawaii, the Ellice, Phoenix, Union, Manihiki and Marquesas groups, Samoa and Tonga, the Cook, Society, Tubuai and Tuamotu groups, and many other lesser islands. (See PACIFIC OCEAN, section on Island, and separate articles on the principal groups, &c.)

The Polynesian Race.-For the ethnological problems offered by Polynesia no thoroughly satisfactory solutions have yet been found. By some the term Polynesian has been treated as a synonym for Malayo-Polynesian, and has been made to include all the brown races of Malaysia, Melanesia, Micronesia and Polynesia. Linguistically, physically and mentally this view is untenable. Whatever be the origin of the Polynesians, they are not Malays, though, themselves of mixed blood, they have probably certain racial elements in common with the latter, who are undoubtedly hybrids. There is every reason to believe that the Polynesians are ethnologically a far older race than the Malays, who, as they now exist, are a comparatively modern people; and thus Friedrich Müller's and D. G. Brinton's theory, that they form a branch of the Malays, fails. Joseph Deniker declares the Polynesians a separate ethnic group of the Indo-Pacific area, and in this view he is followed by A. H. Keane, who suggests that they are a branch of the Caucasic division of mankind who possibly migrated in the Neolithic period from the Asiatic mainland. Of the migration itself no doubt is now felt, but the first entrance of the Polynesians into the Pacific must have been an event so remote that neither by tradition nor otherwise can it be even approximately fixed. The journey of these Caucasians would naturally be in stages. Their carliest halting place was probably the Malay Archipelago, where a few of their kin linger in the Mentawi Islands on the west coast of Sumatra. Thence at a date within historic times a migration eastward took place. The absence of Sanskrit roots in the Polynesian languages appears to indicate that this migration was in pre-Sanskritic times. Whether anything like a definite date can be fixed for it may well be questioned. Abraham Fornander has, however, with great probability, traced back the history of the Hawaiians to the 5th century. He has studied the folk-lore of those islands exhaustively, and from this source comes to the conclusion that the Polynesian migration from the Indian Archipelago may be approximately assigned to the close of the 1st or to the 2nd century. The traditions of many of the Polynesian peoples tend to make Savaii, the largest of the Samoan Islands, their ancestral home in the East Pacific, and linguistic and other evidence goes to 1 An Account of the Polynesian Race (1878), i. 168.

support the theory that the first Polynesian settlement in the | East Pacific was in Samoa, and that thence the various branches of the race made their way in all directions. Most likely Samoa was the first group permanently occupied by them. Owing to the admixture of the Polynesians with the Papuans in Fiji some authorities have thought the first settlement was in those islands, and that the settlers were eventually driven thence by the Papuan occupiers. We can, however, account for the presence of Polynesian blood in Fiji in another way, viz. by the intercourse that has been kept up between the people of Tonga and Fiji. If the first resting-place of the Polynesians was in that group, there is good reason to believe that Samoa was the first permanent home of the race.

It used to be doubted whether these people could have gone from the Indian archipelago so far eastward, because the prevailing winds and currents are from the east. But it is now well known that at times there are westerly winds in the region over which they would have to travel, and that there would be no insuperable difficulties in the way of such a voyage. The Polynesians are invariably navigators. There is ample evidence that in early times they were much better seamen than they are at present. Indeed their skill in navigation has greatly declined since they have become known to Europeans. They used to construct decked vessels capable of carrying one or two hundred persons, with water and stores sufficient for a voyage of some weeks duration. These vessels were made of planks well fitted and sewn together, the joints being caulked and pitched. It is only in recent times that the construction of such vessels has ceased. The people had a knowledge of the stars, of the rising and setting of the constellations at different seasons of the year; by this means they determined the favourable season for making a voyage and directed their

course.

The Polynesians were by no means a savage people when they entered the Pacific. Indeed their elaborate historical legends show that they possessed a considerable amount of civilization. Those who are familiar with these legends, and have studied native manners and customs, see many unmistakable proofs that the Polynesians had, at their migration, considerable knowledge and culture, and that the race has greatly deteriorated.

The Polynesians are physically a very fine race. On some islands they average 5 ft. 10 in. in height. De Quatrefages, in a table giving the stature of different races of men, puts the natives of Samoa and Tonga as the tallest people in the world. He gives 5 ft. 9.92 in. as their average height. They are well developed in proportion to their height. Their colour is a brown, lighter or darker generally according to the amount of their exposure to the sun-being darker on some of the atolls where the people spend much time in fishing, and among fishermen on the volcanic islands, and lighter among women, chiefs and others less exposed than the bulk of the people. Their hair is dark brown or black; smooth and curly, very different from the frizzly mop of the Papuan or the lank straight locks of the Malay. They have very little beard. Their features are generally fairly regular and often beautiful; eyes invariably black, and in some persons oblique; jaws not projecting, except in a few instances; lips of medium thickness; the noses are naturally long, well shaped and arched, but many are artificially flattened at the bridge in infancy. Their foreheads are fairly high, but rather narrow. The young of both sexes are good-looking.

The men often have more regular features than the women, Formerly the men paid more attention to personal appearance than the women. Polynesians generally are of singularly cleanly habits, love bathing, and have a taste for neatness and order. Their clothing is simple: a loin cloth for the men and for the women a girdle or petticoat of leaves. Sometimes women cover the shoulders, and on great occasions the men robe themselves in tapa, bark-cloth. The men are usually 1 Coco-nut, fibre and the gum which exudes from the bread-fruit tree are generally used for "caulking" and "pitching" canoes.

The Human Species (International Scientific Series), pp. 57-60.

tattooed in elaborate designs from the navel to the thigh, and often around mouth and eyes.

As a race the Polynesians are somewhat apathetic. An enervating climate and lavish natural resources incline them to lead easy lives. On the more barren islands, and on those more distant from the equator, they show more energy. Under certain circumstances they become excitable, and manifest a kind of care-for-nothing spirit. As savages they were strict in their religious observances and religion came into almost every action of life, and they have been, in most instances, easily led to accept Christianity. Their essential trait is their perennial cheerfulness, and their fondness for dance and song and every sort of amusement. They are shrewd, intelligent and possess much common sense. Where they have from early years enjoyed the advantages of a good education, Polynesian youths have proved themselves to possess intellectual powers of no mean order. They are almost invariably fluent speakers; with many of them oratory seems to be a natural gift; it is also carefully cultivated. An orator will hold the interest of his heàrers for hours together at a political gathering, and in his speech he will bring in historical allusions and precedents, and will make apt quotations from ancient legends in a manner which would do credit to the best parliamentary orators. Many of them are very brave, and think little of self-sacrifice for others where duty or family honour is concerned.

Polynesian society is divided into the family and the clan. Each clan has a name which is usually borne by one of the oldest members, who is the chief or head for the time being. This clan system no principal chieftainships. But changes have been made in most of doubt generally prevailed in early times, and was the origin of the the islands. In some the head of one clan has become king over several. In many cases large clans have been divided into sections under secondary heads, and have even been subdivided.

As a rule near relations do not intermarry. In some islands this rule is rigidly adhered to. There have been exceptions, however, especially in the case of high chiefs; but usually great care is taken to prevent the union of those within the prescribed limits of consanguinity. Children generally dwell with their kin on the father's side, but they have equal rights on the mother's side, and sometimes they take up their abode with their mother's family. The only names used to express particular relationships are father and mother, son and daughter, brother and sister. There is usually no distinction between brothers (or sisters) and cousins, all the children of brothers and sisters speak of each other as brothers and sisters, and they call uncles and aunts fathers and mothers. Above the relationship of parents all are simply ancestors, no term being used for grandfather which would not equally apply to any more remote male ancestor. In the same way there is no distinctive term for grandchild. A man speaks of his grandchild as his son or daughter, or simply as his child. Polygamy was often practised, especially by chiefs, and also concubinage. In some places a widow was taken by the brother of her deceased husband, or, failing the brother, by some other relative of the deceased, as an additional wife. rule, a divorced wife would not marry again without the consent of Divorce was an easy matter, and of frequent occurrence; but, as a her former husband. An adulterer was always liable to be killed by the aggrieved husband, or by some member of his clan. the culprit himself could not be reached, any member of the clan highly regarded. Perhaps of all the groups Samoa stood highest was liable to suffer in his stead. In some islands female virtue was in this respect. There was a special ordeal through which a bride passed to prove her virginity, and a proof of her immorality brought disgrace upon all her relatives. But in other islands there was much freedom in the relations of the sexes. Owing to the almost promiscuous intercourse which prevailed among a portion of the race, in some groups titles descended through the mother and not through the father. In Hawaii there was a peculiar system of marriage

If

foot races, walking-matches, swimming, archery, cockfighting, 'Wrestling and boxing, a kind of hockey and football, canoe and fishing-matches and pigeon-catching are among their pastimes. Of indoor games they have a number, many being of a gambling nature. Much time is spent, especially after the evening meal, in asking riddles, in rhyming, &c. The recital of songs and myths is a common amusement, and on special occasions there is dancing.. The night-dances were generally accompanied by much indecency and immorality.

Dr Lewis H. Morgan, in Ancient Society, pp. 419-423, makes the Polynesians to have distinctive terms for grandfather, grandmother, grandson and granddaughter. In this he is mistaken. It is evident from his own lists that the Hawaiian kupuna means simply an ancestor. In like manner moopuna simply means a descendant of any generation after the first.