Derivatives of isocamphoric acid, decomposition of isodihydroaminocampholytic acid with nitrous acid . tertiary Weyl^ (1868) suggested that camphoric acid was either a normal ^COOH dibasic acid, CsHl4 > or an hydroxylated acetone acid, ^COOH 1. 0. Aschan, Ann. 316, 209. 2. Roscoe and Schorlemmer, Treatise on Chemistry (1889) vol. Ill,pt . 5, p . 412 . 3. Ann .22, 38, 50 . 4. J. W. Bruhl, Eerichte 24, 3409. 5. Berichte 1, 94. X0H (GqIi40) , in which the hydroxy 1 group functioned, as an acid. v ^00 OH V. Meyer^ (1870) expressed the opinion that it was the normal di-basic acid. N. Men
Derivatives of isocamphoric acid, decomposition of isodihydroaminocampholytic acid with nitrous acid . tertiary Weyl^ (1868) suggested that camphoric acid was either a normal ^COOH dibasic acid, CsHl4 > or an hydroxylated acetone acid, ^COOH 1. 0. Aschan, Ann. 316, 209. 2. Roscoe and Schorlemmer, Treatise on Chemistry (1889) vol. Ill,pt . 5, p . 412 . 3. Ann .22, 38, 50 . 4. J. W. Bruhl, Eerichte 24, 3409. 5. Berichte 1, 94. X0H (GqIi40) , in which the hydroxy 1 group functioned, as an acid. v ^00 OH V. Meyer^ (1870) expressed the opinion that it was the normal di-basic acid. N. Menschutkin2 (1881) in studying the rate of esteri-fication of dibasic acids, concluded that camphoric acid was a ter-tiary acid because of its slow rate of esterification. To him thisseemed to indicate the correctness of Ballos formula , CH3 H2<? C-COOH H20 C-COOH C3H7 0. Friedel4 (1888-1891) made a study of the ethyl esters ofcamphoric acid. He prepared two different mono-ethyl esters, andthe di-ethyl ester. To account for the two series of mono-estershe proposed this formula for camphoric acid:. 7 Friedel was further strengthened in his belief that camphoric acidhad but one carboxyl group by the fact that in titrating it withalkali les3 than one equivalent of the alkali was necessary toproduce color with phenolphthalein. 5 From a similar study of the esters, J. W. Brfthl (1890) andR. Braunschweig6 (1891) came to a different opinion. They prepared 1. Eerichte 3, 116. 24, 3409. 2. Eerichte 14, 2 630. 2J>, 1796. 3. Eerichte i5, 337 . 4. Bull. Soc . (2) 50, 132; (3)3, 849; Comp. rend. 1_13, 825. 12 di-methyl, di-ethyl, ortho-ethyl-allo-methyl, ortho-methyl-allo-ethyl, ortho-methyl, ortho-ethyl, allo-methyl, and alie-ethyl estersof camphoric acid. They designated as ortho the group that was theeasier to esterify and to saponify. Ballos formula^- explainedthe difference in behavior of the ortho and the alio series of es-ters better, in their opinion, than
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