form addition compounds which on the addition of water yield tertiary alcohols, except in the case of ethyl formate, where a secondary alcohol is obtained.
R·CO2C2H5 → R·C |
OMgBr | → R·C |
OMgBr | → | R′ |  C·OH.
|
| OC2H5 | R′ | R′ | ||||
| R′ | R′ | R′ | ||||
| H·CO2C2H5 → H·C |
OMgBr | → H·C |
OMgBr | → R′ R′  CH·OH.
| ||
| OC2H5 | R′ | |||||
| R′ | R′ | |||||
N. Menschutkin (Ber., 1882, 15, p. 1445; Ann., 1879, 195, p. 334) examined the rate of esterification of many acids with alcohols. It was found that the normal primary alcohols were all esterified at about the same rate, the secondary alcohols more slowly than the primary, and the tertiary alcohols still more slowly. The investigation also showed that the nature of the acid used affected the result, for in an homologous series of acids it was found that as the molecule of the acid became more complex, the rate of esterification became less. The formation of an ester by the interaction of an acid with an alcohol is a “reversible” or “balanced” action, for as M. Berthelot and L. Péan de St Gilles (Ann. Chim. Phys., 1862 (3), 65, p. 385 et seq.) have shown in the case of the formation of ethyl acetate from ethyl alcohol and acetic acid, a point of equilibrium is reached, beyond which the reacting system cannot pass, unless the system be disturbed in some way by the removal of one of the products of the reaction. V. Meyer (Ber., 1894, 27, p. 510 et seq.) showed that in benzenoid compounds ortho-substituents exert a great hindering effect on the esterification of alcohols by acids in the presence of hydrochloric acid, this hindering being particularly marked when two substituents are present in the ortho positions to the carboxyl group. In such a case the ester is best prepared by the action of an alkyl halide on the silver salt of the acid, and when once prepared, can only be hydrolysed with great difficulty.
Ethyl formate, H·CO2C2H5, boils at 55° C. and has been used in the artificial preparation of rum. Ethyl acetate (acetic ether), CH3·CO2C2H5, boils at 75° C. Isoamylisovalerate, C4H9·CO2C5H11, boils at 196° C. and has an odour of apples. Ethyl butyrate, C3H7·CO2C2H5, boils at 121° C. and has an odour of pineapple. The fats (q.v.) and waxes (q.v.) are the esters of the higher fatty acids and alcohols. The esters of the higher fatty acids, when distilled under atmospheric pressure, are decomposed, and yield an olefine and a fatty acid.
Esters of the mineral acids are also known and may be prepared by the ordinary methods as given above. The neutral esters are as a rule insoluble in water and distil unchanged; on the other hand, the acid esters are generally soluble in water, are non-volatile, and form salts with bases. Ethyl hydrogen sulphate (sulphovinic acid), C2H5·HSO4, is obtained by the action of concentrated sulphuric acid on alcohol. The ester is separated from the solution by means of its barium salt, and the salt decomposed by the addition of the calculated amount of sulphuric acid. It is a colourless oily liquid of strongly acid reaction; its aqueous solution decomposes on standing and on heating it forms diethyl sulphate and sulphuric acid. Dimethyl sulphate, (CH3)2SO4, is a colourless liquid which boils at 187°-188° C., with partial decomposition. It is used as a methylating agent (F. Ullmann). Great care should be taken in using dimethyl and diethyl sulphates, as the respiratory organs are affected by the vapours, leading to severe attacks of pneumonia. Ethyl nitrate, C2H5·ONO2, is a colourless liquid which boils at 86.3° C. It is prepared by the action of nitric acid on ethyl alcohol (some urea being added to the nitric acid, in order to destroy any nitrous acid that might be produced in secondary reactions and which, if not removed, would cause explosive decomposition of the ethyl nitrate). It burns with a white flame and is soluble in water. When heated with ammonia it yields ethylamine nitrate, and when reduced with tin and hydrochloric acid it forms hydroxylamine (q.v.) (W. C. Lossen). Ethyl nitrite, C2H5·ONO, is a liquid which boils at 18° C.; the crude product obtained by distilling a mixture of alcohol, sulphuric and nitric acids and copper turnings is used in medicine under the name of “sweet spirits of nitre.” Amyl nitrite, C5H11·ONO, boils at 96° C. and is used in the preparation of the anhydrous diazonium salts (E. Knoevenagel, Ber., 1890, 23, p. 2094). It is also used in medicine.
ESTHER. The Book of Esther, in the Bible, relates how a
Jewish maiden, Esther, cousin and foster-daughter of Mordecai,
was made his queen by the Persian king Ahasuerus (Xerxes)
after he had divorced Vashti; next, how Esther and Mordecai
frustrated Haman’s endeavour to extirpate the Jews; how
Haman, the grand-vizier, fell, and Mordecai succeeded him;
how Esther obtained the king’s permission for the Jews to
destroy all who might attack them on the day which Haman
had appointed by lot for their destruction; and lastly, how the
feast of Purim (Lots?) was instituted to commemorate their
deliverance. Frequent incidental references are made to Persian
court-usages (explanations are given in i. 13, viii. 8), while on
the other hand the religious rites of the Jews (except fasting),
and even Jerusalem and the temple, and the name of Israel,
are studiously ignored. Even the name of God is not once
mentioned, perhaps from a dread of its profanation during the
Saturnalia of Purim. The early popularity of the book is shown
by the interpolated passages in the Septuagint and the Old
Latin versions.
The criticism of Esther began in the 18th century. As soon as the questioning spirit arose, the strangeness of many statements in the book leaped into view. A moderate scholar of our day can find no historical nucleus, and calls it a sort of historical romance.[1] The very first verses in the book startle the reader by their exaggerations, e.g. a banquet lasting 180 days, “127 provinces.” Farther on, the improbabilities of the plot are noticeable. Esther, on her elevation, keeps her Jewish origin secret (ii. 10; cf. vii. 3 ff.), although she has been taken from the house of her uncle, who is known to be a Jew (iii. 4; cf. vi. 13), and has remained in constant intercourse with him (ii. 11, 19, 20, 22; cf. iv. 4-17). We are further told that the grand-vizier was an Agagite or Amalekite (iii. 1, &c.); would the nobility of Persia have tolerated this? Or did Haman too keep his non-Persian origin secret? Also that Mordecai offered a gross affront to Haman, for which no slighter punishment would satisfy Haman than the destruction of the whole Jewish race (iii. 2-6). Of this savage design eleven months’ notice is given (iii. 12-14); and when the danger has been averted by the cleverness of Esther, the provincial Jews are allowed to butcher 75,000, and those in the capital 800 of their Persian fellow-subjects (ix. 6-16).
It is urged, on the other hand, that the assembly mentioned in i. 3 may be that referred to by Herodotus (vii. 8) as having preceded the expedition against Greece. This hypothesis, however, requires us to suppose that Xerxes had returned from Sardis to Susa by the tenth month of the seventh year of his reign, which is barely credible. In the reckoning of 127 provinces (cf. Dan. vi. 1; 1 Esd. iii. 2) satrapies and sub-satrapies may be confounded. It is at any rate correct to include India among the provinces; this is justified, not only by Herodotus (iii. 94), but by the inscriptions of Darius at Persepolis and Naksh-i-Rustam. Herodotus again (vii. 8) confirms the custom referred to in Esth. ii. 12. But what authority can make the conduct of Mordecai credible? To-day the harem is impenetrable, while “any one declining to stand as the grand-vizier passes is almost beaten to death.”[2] This, surely, is what a real Mordecai would have suffered from a real Haman. Even the capricious Xerxes would never have permitted the entire destruction of one of the races of the empire, nor would a vizier have proposed it.
Serious difficulties of another kind remain. Mordecai is represented as a fellow-captive of Jeconiah (597 B.C.), and grand-vizier in Xerxes’s twelfth year (474 B.C.)! This is parallel to the strange statement in Tobit xiv. 15. And how can we find room for Esther as queen by the side of Amestris (Herod. vii. 14, ix. 112)? How, too, can a Jewess have been a legal queen (see Herod. iii. 84)? Then take the supposed Persian proper names. “Ahasuerus” may no doubt stand, but very few of the rest (see Nöldeke, Ency. Bib. col. 1402). As to the style, the general verdict is that it points to a late date (see Driver, Introd.6, p. 484). Altogether, critics decline to date the book earlier than the 3rd or even 2nd century B.C.
So far we have only been carrying on 18th-century criticism. In more recent years, however, new lines of inquiry have been opened up. First of all by the great Semitic scholar Lagarde. His thesis (seldom defended now) was that Purim corresponds to Fūrdigan, the name of the old Persian New Year’s and All Souls’ festival held in spring, on which the Persians were wont to exchange presents (cf. Esth. ix. 19). In 1891 came a new explanation of Esther from Zimmern. It is true that in its earlier form his theory was very incomplete. But in justice to this scholar we may notice that from the first he looked for light to Babylonia, and that many other critics now take up the same
