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LAEVULINIC ACID ((3-acetopropionic ac...

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Originally appearing in Volume V16, Page 66 of the 1911 Encyclopedia Britannica.
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LAEVULINIC

ACID ((3-acetopropionic acid), C5H803  or CH3CO•CH2•CH2•CO2H, a ketonic acid prepared from laevulose, inulin,
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starch, &c., by boiling them with dilute hydrochloric or sulphuric acids . It may be synthesized by condensing sodium acetoacetate with monochloracetic ester, the acetosuccinic ester produced being then hydrolysed with dilute hydrochloric acid (M . Conrad,
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Ann., 1877, 188, p . 222) . CH,•CO•CH•Na CH 3•CO•CH•CH2•CO2R —> I -CH3000H2•CH2•CO2OH . CO2R CO2R It may also be prepared by
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heating the anhydride of y-methyloxyglutaric acid with concentrated sulphuric acid, and by oxidation of methyl heptenone and of geraniol . It crystallizes in plates, which melt at 32'5-33° C. and
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boil at 148-149° (15 mm.) (A . Michael, four. prak . Chem., 1891 [2], 44, p . 114) . It is readily soluble in
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alcohol, ether and
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water . The acid, when distilled slowly, is decomposed and yields a and (3-
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angelica
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lactones .

When heated with hydriodic acid and

phosphorus, it yields n-valeric acid; and with iodine and caustic soda solution it gives iodoform, even in the cold . With hydroxylamine it yields an oxime, which by the
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action of concentrated sulphuric acid rearranges itself to N-methylsuccinimide [CH2•CO]2N•CH3 . LA FARGE, JOHN (1835—1910),
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American artist, was born in New York, on the 31st of March 1835, of French parentage . He received instruction in
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drawing from his grandfather, Binsse de St Victor, a painter of miniatures; studied law and architecture; entered the atelier of Thomas Couture in Paris, where he remained a short time, giving especial attention to the study and copying of old masters at the Louvre; and began by making illustrations to the poets (1859) . An intimacy with the artist William M . Hunt had a strong influence on him, the two working together at
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Newport, Rhode Island . La Farge painted landscape, still
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life and figure alike in the early sixties . But from 1866 on he was for some time incapacitated for
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work, and when he regained strength he did some decorative work for Trinity church, Boston, in 1876, and turned his attention to stained glass, becoming president of the Society of Mural Painters . Some of his important commissions include windows for St Thomas's church (1877), St Peter's church, the Paulist church, the Brick church (1882), the churches of the Incarnation (1885) and the Ascension (1887), New York; Trinity church,
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Buffalo, and the "
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Battle Window " in Memorial Hall at Harvard; ceilings and windows for the house of Cornelius Vanderbilt, windows for the houses of W . H . Vanderbilt and D . 0 .

Mills, and panels for the house of Whitelaw Reid, New York; panels for the Congressional Library, Washington; Bowdoin College, the Capitol at St Paul, Minn., besides designs for many stained glass windows . He was also a prolific painter in oil and water colour, the latter seen notably in some water-colour sketches, the result of a voyage in the South Seas, shown in 1895 . His influence on American
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art was powerfully exhibited in such men as Augustus St Gaudens,
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Wilton Lockwood, Francis Lathrop and John Humphreys Johnston . He became president of the Society of American Artists, a member of the
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National Academy of Design in 1869; an officer of the Legion of Honour of France; and received many medals and decorations . He published Considerations on
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Painting (New York, 1895), Hokusai: A Talk about Hoksuai (New York, 1897), and An Artist's Letters from
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Japan (New York, 1897) . See Cecilia Waern, John La Farge, Artist and Writer (
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London, 1896, No . 26 of The Portfolio) . LA FARINA, GIUSEPPE (1815-1863),
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Italian author and politician, was born at
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Messina . On account of the
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part he took in the insurrection of 1837 he had to leave Sicily, but returning in 1839 he conducted various
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newspapers of liberal tendencies, until his efforts were completely interdicted, when he removed to Florence . In 184o he had published Messina ed i suoi monumenti, and after his removal to Florence he brought out La Germania
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coi suoi monumenti (1842), L' Italia coi suoi monuments (1842), La Svizzera storica ed artistica (1842—1843), La
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China, 4 vols . (1843—1847), and Storia d' Italia, 7 vols . (1846—1854)• In 1847 he established at Florence a democratic journal, L'
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Alba, in the interests of Italian freedom and unity, but on the outbreak of the revolution in Sicily in 1848 he returned thither and was elected deputy and member of the committee of war .

In

August of that,
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year he was appointed minister of public instruction and later of war and marine . After vigorously conducting a
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campaign against the Bourbon troops, he was forced into exile, and repaired to France in 1849 . In 1850 he published his Storia documentata della Rivoluzione Siciliana del 1848—1849, and in 1851—1852 his Storia d' Italia dal 1815 al 1848, in 6 vols . He returned to Italy in 1854 and settled at
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Turin, and in 1856 he founded the Piccolo Corriere d' Italia, an
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organ which had
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great influence in propagating the
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political sentiments of the Society Nazionale Italiana, of which he ultimately was chosen president . With Daniele Manin (q.v.), one of the founders of that society, he advocated the unity of Italy under Victor Emmanuel even before Cavour, with whom at one time he had daily interviews, and organized the emigration of
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volunteers from all parts of Italy into the Piedmontese army . He also negotiated an interview between Cavour and Garibaldi, with the result that the latter was appointed
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commander of the Cacciatori delle Alpi in the war of 1859 . Later he supported Garibaldi's expedition to Sicily, where he himself went soon after the occupation of Palermo, but he failed to bring about the immediate annexation of the island to Piedmont as Cavour wished . In 186o he was chosen a member of the first Italian parliament and was subsequently made councillor of state . He died on the 5th of September 1863 . See A . Franchi, Epistolario di Giuseppe La Farina (2 vols., 1869) and L . Carpi, Il Risorgimento Italiano, vol. i .

(

Milan, 1884) . LA FAYETTE, GILBERT MOTIER DE (138o-1462), marshal of France, was brought up at the court of Louis II., 3rd duke of Bourbon . He served under Marshal Boucicaut, in Italy, and on his return to France after the evacuation of Genoa in 1409 became seneschal of the Bourbonnais . In the
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English
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wars he was with John I., 4th duke of Bourbon, at the capture of Soubise in 1413, and of
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Compiegne in 1415 . The duke then made him
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lieutenant-general in
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Languedoc and
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Guienne . He failed to defend
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Caen and
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Falaise in the
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interest of the dauphin (after-wards Charles VII.) against Henry V. in 1417 and 1418, but in the latter year he held Lyons for some time against
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Jean sans Peur, duke of
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Burgundy . A series of successes over the English and Burgundians on the
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Loire was rewarded in 1420 with the government of Dauphiny and the office of marshal of France . La Fayette commanded the Franco-Scottish troops at the battle of Bauge (1422), though he did not, as has been sometimes stated, slay Thomas, duke of Clarence, with his own hand . In 1424 he was taken prisoner by the English at Verneuil, but was released shortly afterwards, and fought with
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Joan of Arc at Orleans and Patay in 1429 . The marshal had become a member of the
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grand council of Charles VII., and with the exception of a short disgrace about 1430, due to the
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ill-will of Georges de la Tremouille, he retained the royal favour all his life . He took an active part in the army reform initiated by Charles VII., and the establishment of military posts for the suppression of brigand-age . His last campaign was against the English in
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Normandy in 144Q .

He died on the 23rd of

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February 1462 . His
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line was continued by Gilbert IV. de La Fayette, son of his second
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marriage with Jeanne de Joyeuse . LA FAYETTE, LOUISE DE (c . 1616-1665), was one of the fourteen children of John, comte de La Fayette, and
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Marguerite de Bourbon-Busset . Louise became maid of honour to Anne of Austria, and Richelieu sought to attract the attention of Louis XIII. to her in the hope that she might counterbalance the influence exercised over him by
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Marie de Hautefort . The affair did not turn out as the minister wished . The king did indeed make her the confidante of his affairs and of his resentment against the cardinal, but she, far from repeating his confidences to the minister, set hgrself to encourage the king in his resistance to Richelieu's dominion . She refused, nevertheless, to become Louis's
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mistress, and after taking leave 'of the king in Anne of Austria's presence retired to the convent of the Filles de Sainte-Marie in 1637 . Here she was repeatedly visited by Louis, with whom she maintained a correspondence . Richelieu intercepted the letters, and by omissions and falsifications succeeded in destroying their mutual confidence . The cessation of their intercourse was regretted by the queen, who had been reconciled with her
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husband through the influence of Louise . At the time of her
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death in
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January 1665 Mlle de La Fayette was
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superior of a convent of her order which she had founded at Chaillot .

See Memoires de Madame de

Motteville; Victor Cousin, Madame de Hautefort (Paris, 1868) ; L'Abbe Sorin, Louise-Angele de La Fayette (Paris, 1893) . LA FAYETTE, MARIE JOSEPH PAUL YVES ROCH GILBERT DU MOTIER,
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MARQUIS DE (1757-1834), was born at the chateau of Chavaniac in
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Auvergne, France, on the 6th of September 1757 . His
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father' was killed at
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Minden in 1759, and his
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mother and his grandfather died in 1770, and thus at the age of thirteen he was
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left an
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orphan with a princely fortune . He married at sixteen Marie Adrienne Francoise de
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Noailles (d . 1807), daughter of the duc d'Ayen and granddaughter of the duc de Noailles, then one of the most influential families in the
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kingdom . La Fayette chose to follow the career of his father, and entered the Guards . La Fayette was nineteen and a captain of dragoons when the English colonies in
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America proclaimed their independence . " At the first
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news of this
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quarrel," he afterwards wrote in his
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memoirs, " my heart was enrolled in it." The count de
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Broglie, whom he consulted, discouraged his zeal for the cause of liberty . Finding his purpose unchangeable, however, he presented the young enthusiast to Johann Kalb, who was also seeking service in America, and through Silas Deane, American agent in Paris, an arrangement was concluded, on the 7th of December 1776, by which La Fayette was to enter the American service as major-general . At this moment the news arrived of
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grave disasters to the American arms . La Fayette's friends again advised him to abandon his purpose . Even the American envoys, Franklin and Arthur Lee, who had superseded Deane, withheld further encouragement and the king himself forbade his leaving .

At the instance of the

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British ambassador at
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Versailles orders were issued to seize the
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ship La Fayette was fitting out at
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Bordeaux, and La Fayette himself was arrested . But the ship was sent ' The
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family of La Fayette, to the cadet branch of which he be-longed, received its name from an estate in
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Aix, Auvergne, which belonged in the 13th century to the Motier family . xvI . 3from Bordeaux to a neighbouring
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port in Spain, La Fayette escaped from custody in disguise, and before a second lettre de cachet could reach him he was afloat with eleven chosen companions . Though two British cruisers had been sent in pursuit of him, he landed safely near
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Georgetown, S.C., after a tedious voyage of nearly two months, and hastened to
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Philadelphia, then the seat of government of the colonies . When this lad of nineteen, with the command of only what little English he had been able to pick up on his voyage, presented himself to Congress with Deane's authority to demand a commission of the highest rank after the commander-in-chief, his reception was a little chilly . Deane's contracts were so numerous, and for
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officers of such high rank, that it was impossible for Congress to ratify them without injustice to Americans who had become entitled by their service to promotion . La Fayette appreciated the situation as soon as it was explained to him, and immediately expressed his
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desire to serve in the American army upon two conditions—that he should receive no pay, and that he should act as a volunteer . These terms were so different from those made by other foreigners, they had been attended with such substantial sacrifices, and they promised such import-ant indirect advantages, that Congress passed a
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resolution, on the 31st of
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July 1977, " that his services be accepted, and that, in consideration of his zeal, illustrious family and connexions, he have the rank and commission of major-general of the
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United States." Next day La Fayette met Washington, whose lifelong friend he became . Congress intended his appointment as purely honorary, and the question of giving him a command was left entirely to Washington's discretion . His first battle was
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Brandy-wine (q.v.) on the 11th of September 1777, where he showed courage and activity and received a wound . Shortly afterwards he secured what he most desired, the command of a division—the immediate result of a communication from Washington to Congress of November 1, 1777, in which he said: " The marquis de La Fayette is extremely solicitous of having a command equal to his rank .

I do not know in what

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light Congress will view the
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matter, but it appears to me, from a consideration of his illustrious and, important connexions, the
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attachment which he has manifested for our cause, and the consequences which his return in disgust might produce, that it will be advisable to gratify his wishes, and the more so as several gentlemen from France who came over under some assurances have gone back disappointed in their expectations . His conduct with respect to them stands in a favourable point of view—having interested himself to remove their uneasiness and urged the impropriety of their making any unfavourable representations upon their arrival at home . Besides, he is sensible, discreet in his manners, has made great proficiency in our language, and from the disposition he discovered at the battle of
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Brandywine possesses a large share of bravery and military ardour." Of La Fayette's military career in the United States there is not much to be said . Though the commander of a division, he never had many troops in his charge, and whatever military talents he possessed were not of the kind which appeared to conspicuous
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advantage on the theatre to which his
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wealth and family influence rather than his soldierly gifts had called him . In the first months of 1778 he commanded troops detailed for the projected expedition against
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Canada . His retreat from Barren Hill (May 28, 1778) was commended as masterly; and he fought at the battle of Monmouth (
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June 28) and received from Congress a formal recognition of his services in the Rhode Island expedition (August 1778) . The
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treaties of commerce and defensive
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alliance, signed by the insurgents and France on the 6th of February 1778, were promptly followed by a declaration of war by England against the latter, and La Fayette asked leave to revisit France and to consult his king as to the further direction of his services . This leave was readily granted; it was not difficult for Washington to replace the major-general, but it was impossible to find another equally competent, influential and devoted champion of the American cause near the court of Louis XVI . In fact, he went on a
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mission rather than a visit . He embarked on the
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ruth of January 1779, was received with
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enthusiasm, and was made a colonel in the French cavalry . On the 4th of March following Franklin wrote to the president of Congress: " The marquis de La Fayette .. . is infinitely esteemed and beloved here, and I am persuaded will II do everything in his power to merit a continuance of the same affection from America." He won the confidence of Vergennes .

La Fayette was absent from America about six months, and his return was the occasion of a complimentary resolution of Congress . From

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April until
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October 1781 he was charged with the defence of Virginia, in which Washington gave him the credit of doing all that was possible with the forces at his disposal; and he showed his zeal by borrowing
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money on his own account to provide his soldiers with necessaries . The battle of
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Yorktown, in which La Fayette
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bore an honourable if not a distinguished part, was the last of the war, and terminated his military career in the United States . He immediately obtained leave to return to France,where it was supposed he might be useful in negotiations for a general peace . He was also occupied in the preparations for a combined French and
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Spanish expedition against some of the British West India Islands, of which he had been appointed chief of staff, and a formidable
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fleet assembled at Cadiz, but the armistice signed on the loth of January 1783 between the belligerents put a stop to the expedition., He had been promoted (1781) to the rank of marechal de camp (major-general) in the French army, and he received every token of regard from his
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sovereign and his countrymen . He visited the United States again in 1784, and remained some five months as the guest of the nation . La Fayette did not appear again prominently in public life until 1787, though he did good service to the French Protestants, and became actively interested in plans to abolish
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slavery . In 1787 he took his seat in the Assembly of Notables . He demanded, and he alone signed the demand, that the king convoke the states-general, thus becoming a leader in the French Revolution . He showed Liberal tendencies both in that assembly and after its dispersal, and in 1788 was deprived, in consequence, of his active command . In 1789 La Fayette was elected to the states-general, and took a prominent part in its proceedings . He was chosen
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vice-president of the National Assembly, and on the 11th of July 1789 presented a declaration of rights, modelled on Jefferson's Declaration of Independence in 1776 .

On the 15th of July, the second day of the new regime, La Fayette was chosen by

acclamation colonel-general of the new National Guard of Paris . He also proposed the combination of the colours of Paris, red and blue, and the royal white, into the famous tricolour cockade of
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modern France (July 17) . For the succeeding three years, until the end of the constitutional monarchy in 1792, his
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history is largely the history of France . His life was beset with very great responsibility and perils, for he was ever the minister of humanity and order among a frenzied
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people who had come to regard order and humanity as phases of treason . He rescued the queen from the hands of the populace on the 5th and 6th of October 1789, saved many humbler victims who had been condemned to death, and he risked his life in many unsuccessful attempts to rescue others . Before this, disgusted with enormities which he was powerless to prevent, he had resigned his commission; but so impossible was it to replace him that he was induced to resume it . In the Constituent Assembly he pleaded for the abolition of arbitrary imprisonment, for religious tolerance, for popular representation, for the establishment of trial by
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jury, for the gradual emancipation of slaves, for the freedom of the press, for the abolition of titles of
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nobility, and the suppression of privileged orders . In February 1790 he refused the supreme command of the National Guard of the kingdom . In May he founded the " Society of 1789 " which afterwards became the Feuillants Club . He took a prominent part in the celebration of July 14, 1790, the first anniversary of the destruction of the Bastille . After suppressing an emeute in April 1791 he again resigned his commission, and was again compelled to retain it . He was the friend of liberty as well as of order, and when Louis XVI. fled to Varennes he issued orders to stop him .

Shortly afterwards he was made lieutenant-general in the army . He commanded the troops in the suppression of another emeute, on the occasion of the

proclamation of the constitution (September 18, 1791), after which, feeling that his task was done, he retired into private life .

End of Article: LAEVULINIC ACID ((3-acetopropionic acid), C5H803
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