Glycine, and acetic acid

This year has seen the application of carbohydrates in the synthesis of enantiomerically pure acids, amino acids and diols, including those containing isotopic labels. l,2 5,6-Di- >-isopropylidene-a-D-glucofuranose has been converted to diastereomerically pure epoxide 102 and diol 103 and the reactivity of these units has been exploited for the synthesis of enantiomerically pure labelled glycine and acetic acid, as well as 1,2-diols (Scheme 2 )P ... 

If a phenol is not indicated, the solution may contain an aliphatic acid. Transfer to a distilling-flask, make definitely acid with dih H2SO4, and distil the volatile formic and acetic acids if present will distil over. If the distillation gives negative reactions, test the residual solution in the flask for oxalic, succinic, lactic, tartaric and citric acids and glycine, remembering that the solution is strongly acid. 

A. AcetamidoaceUme. A mixture of 75.0 g. (l.O mole) of glycine (Note 1), 475 g. (485 ml., 6 moles) of pyridine (Note 1), and 1190 g. (1.1 1., 11.67 moles) of acetic anhydride (Notes 1 and 2) is heated under reflux with stirring for 6 hours (Note 3) in a 3-1., three-necked, round-bottomed flask. The reflux condenser is replaced by one set for downward distillation, and the excess pjnidine, acetic anhydride, and acetic acid are removed by distillation under reduced pressure. The residue is transferred to a simple distillation apparatus such as a Claisen flask and is distilled to give 80-90 g. (70-78%) of a pale yellow oil, b.p. 120-125° (1 mm.). This product is of satisfactory purity for use in step B. 

C6H8N N)2N.CH2.COOH mw 283.28, N 24.72% crysts m" expl 124° was prepd from glycine(amino-acetic acid), NaOH and benzene-diazonium chloride at 0°... 

Experiment 5.181 AMINOACETONITRILE AND GLYCINE (Amino-acetic acid)... 

The presence of fixation of CO by minerals led to acetate, pyruvate, acetaldehyde, glycerol-aldehyde, acetone, methyl mercaptan (also called methanethiol), methyl-thioacetate, glycine, and aspartic acid. Alanine forms by reduction of pyruvate with ammonia. Iron sulfide and hydrogen sulfide reduce molecular nitrogen to ammonia according to the overall reaction ... 

A mixture of Z-menthyl glycine [39] (19.7 g, 92 mmol), isoamyl nitrite (12.0 g, 100 mmol), and acetic acid (1.6 g, 27 mmol) in chloroform (400 mL) was heated under reflux for 25 min [40]. The reaction mixture was washed with IM sulfuric acid, with a saturated aqueous solution of sodium bicarbonate, and finally with water. After removal of the solvent, the residue was purified by column chromatography on silica gel (160 g, methylene chloride) to give yellow waxy crystals (15.0 g, 73%), [a]p-86.8 ° (c 1.0, chloroform), IR t) 2125 cm (film) and H-NMR 8 5.29 ppm (chloroform-d, TMS). 

Suppose one were to titrate an equimolal mixture of ammonium chloride and acetic acid with two equivalents of sodium hydroxide. How would the neutralization of acetic acid and ammonium chloride be expected to differ from that of glycine hydrochloride shown in the figure below ... 

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