The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Hydrolysis of trimethylethylene bromide. Mechanism of ketone formation》. Authors are Suter, C. M.; Zook, Harry D..The article about the compound:2,3-Dibromopropionic acidcas:600-05-5,SMILESS:O=C(O)C(Br)CBr).HPLC of Formula: 600-05-5. Through the article, more information about this compound (cas:600-05-5) is conveyed.
The conversion of Me2CBrCHBrMe (I) into Me2CHAc (II) proceeds in steps through Me2C(OH)CHBrMe (III) and Me2C(OH)CH(OH)Me (IV) as evidenced by rate measurements on the hydrolysis of I and III and on the conversion of IV to II. Preliminary experiments with Me2CBrCH2Br (V) indicate that a similar mechanism holds for the hydrolysis of this compound The V used b17 55°, m. 9-12°. The purest I prepared b19 63°, m. 14-16°, n20D 1.5090; the fraction used in this work m. 12-13°, d254 1.663, n25D 1.5078. III b14 48°, n25D 1.4710; it is unstable and after 30 days gives a dark green mixture containing I, III and II; it decomposes on distillation at 100°. Me2C:CH2 and Br-KBr in H2O give Me2C(OH)CH2Br, b16 49.5°, d254 1.437, n25D 1.4710, which is stable almost indefinitely. II was determined by reaction with NH2OH.HCl, the liberated acid being titrated and plotted against the concentration of II. III can be titrated with standard alkali in hot solution, using phenolphthalein; the distribution ratio of the III between the 2 phases of a system containing H2O, dioxane and CCl4 was convenient for anal. of the aqueous layer.
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Reference:
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