Naming acids

Langmuir also gave needed emphasis to the importance of employing pure substances rather than the various natural oils previously used. He thus found that the limiting area (at the Pockels point) was the same for palmitic, stearic, and cerotic acids, namely, 21 per molecule. (For convenience to the reader, the common names associated with the various hydrocarbon derivatives most frequently mentioned in this chapter are given in Table IV-1.)... 

Trivial acid names are formed by changing the endings -oic acid or -ic acid to -onitrile. For example, CH3CN is acetonitrile. When the —CN group is not the highest priority group, the —CN group is denoted by the prefix cyano-. 

This article uses the former nomenclature. Organoperoxysulfonic acids are named by inserting peroxy in the sulfonic acid name, eg, cyclohexaneperoxysulfonic acid [74232-61 ]. For diacids, the prefixes monoperoxy- or diperoxy- are used, eg, monoperoxysuccinic acid and diperoxyisophthahc acid [1786-87 ]. 

An important aspect of this procedure is the use of latent acid catalysts, such as phenyl hydrogen maleate, phenyl trifluoracetate, and butadiene sulfone. These catalysts reduce the peak exotherm from over 200°C to 130—160°C. The resin catalyst mixture has a working life of up to several days at RT. The elevated temperature of mol ding these latent catalysts generates the corresponding acids, namely, maleic, trifluoracetic, and phenolsulfonic, which cataly2e the resole reaction. Typically, a cycle time of 1—2 min is requited for a mold temperature of - 150° C. 

Acid halides are named by identifying first the acyl group and then the halide. The acyl group name is derived from the carboxylic acid name by replacing the -ic acid ending with -yl or the -carboxylic acid ending with -carbonyl, as described previously in Section 20.1 and shown in Table 20.1 on page 753. For example ... 

Acid Name of Acid Base Name of Base... 

The Common a-Amino Acids (names and abbreviations below structures)... 

Write equations for the reaction of (a) ethanol and formic acid (b) propanol and propionic acid (c) methanol and formic acid. Name the esters produced. 

TABLE P a 10.3 Conjugate Acid-Base Pairs Arranged by Strength Acid name Acid formula Base formula Base name PKb... 

In the formation of C6 acids (namely, organic acids containing 6 or fewer carbon atoms), at OH concentrations greater than 10 mM, route 5 occurs preferentially to route 6, and lactic acid and saccharinic acids predominate in the product,... 

The precursors for >C6 acids (namely, >C6 oi-dicarbonyls) are assumed to form by aldol condensation of ot-dicarbonyl compounds with other carbonyl compounds (route 7), and termination of this oligomerization is... 

Some cyclopropylcarboxylic acids, namely 14 [125] and 15 [46] could be coupled to bicyclopropyl compounds, others led to allylic compounds via ring opening of an intermediate carbenium ion (see chap. 7). Tertiary alkanoates yield predominantly non-Kolbe products (see chap. 8). 

The 2 1 reaction of 9-BBN with a series of dicarboxylic acids, namely oxalic acid, malonic acid, 2,2-dimethylmalonic acid, and succinic acid, in dimeth-oxyethane gives in some cases dimeric and in other cases macrocyclic (acyloxy)diorganoboranes. This has been proved by IR spectroscopy (all C = O groups are bidentate), B-NMR 5 = 10 ppm) and X-ray crystallography [47]. With oxalic acid two structures are possible (IV and V), of which the first with a five-membered boron heterocycle instead of a four-membered one is the more probable formulation (Fig. 13). 

All sixteen of the racemic carba-sugars predicted are known, as well as fifteen of the enantiomers. The most accessible starting-material for the synthesis of racemic carba-sugars is the Diels-Alder adduct of furan and acrylic acid, namely, e i o7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylicacid (29). Furthermore, adduct 29 is readily resolved into the antipodes, (—)-29 and (+)-29, by use of optically active a-methylbenzylamine as the resolution agent. The antipodes were used for the synthesis of enantiomeric carba-sugars by reactions analogous to those adopted in the preparation of the racemates. 

Epimerization at C-5 of hexuronic acids is a reaction that proceeds both on the polymer and on the sugar nucleotide level. In addition to the three pairs of parent acids, namely, the u-glucolL-ido-, D manno/L-gulo-, and D-ga-lacto/L-altro-he uron c acids, the 2-amino-2-deoxy acids belonging to the last two and the 2,3-diamino-2,3-dideoxy acids belonging to the middle pair have been found. 

The presence of the denominator term in the rate equation (17) suggests that the equilibrium (18) precedes the oxidation step. Two sequences of reactions are proposed (see below), depending on whether the sulphite radical ion dimerises (20) or attacks further acid chromate ion (21). It should be noted that of the species prevalent in dilute aqueous chromic acid, namely CrOj , Cr207, HCrO and H2Cr04, only the last is regarded as possessing oxidising powers. This fact, noted by Westheimer , is tacitly assumed in all recent discussion of... 

The GC-MS data (Figure 16.11) of the violet zone of B. carterii revealed that the unchanged diterpenes (verticillatriene, cembrene A, and cembrene C) and the nortriterpenes with carbohydrate structure originated from the pyrolyzed triterpenes (Figure 16.12) of the a- and (3-boswellic acids, named 24-norursa-3,12-diene (compound 7), 24-norursa-3,9(ll),12-triene (compound 8), 24-noroleana-3,12-diene (compound 9), and 24-noroleana-3,9(ll),12-triene (compound 10). 

Vercellotti and associates121,126 were the first to apply the Helferich -Wedemeyer procedure127 (which uses mercury dicyanide as the acid acceptor) for the preparation of a glycosylamino acid, namely, 3-0-(2-acetamido-3,4,6-tri-0-acetyl-2-deoxy-/ -D-glucopyranosyl)-N-(2,4-di-nitrophenyl)-L-serine and -DL-threonine methyl ester derivatives (162). 

Enantiomerically pure 4,5,6-trihydroxy-norleucins (for instance 325) were obtained (197) from the hex-2-enono-1,4-lactone-2-mesylates (such as 152). These butenolides were stereoselectively hydrogenated to afford, upon treatment with sodium azide, the C-2-inverted derivatives, such as 324. Reduction of the azide function and hydrolysis of the acetal group gave the amino acids (namely 325), which were converted into lactones in acid media. 

A pentaacyl lipid A is also found in R. sphaeroides (Fig. 7) (88). This lipid A has the same distribution of fatty adds as B.fragilis (79) but, as a notable feature, it contains two rare types of fatty acids, namely, A7-14 1 and 14 0(3-oxo), the former being present as a 3-acyloxytetradecanoic acid group amide-linked to GlcN (II), the latter being amide-bound to GlcN(I). 

The napkthols are in many respects still more reactive than phenol. This is shown most distinctly by the fact that the naphthyl ethers can be obtained by the method used for the preparation of esters of carboxylic acids, namely, directly by the action of hydrogen chloride on the phenol in the presence of the alcohol. The naphthols, moreover, react readily with zinc-ammonium chloride and with ammonium sulphite and ammonia to yield naphthylamines. The second of these two methods is a general one. It was investigated by H. Bucherer. 

Ternary acids are usually named with the suffixes ic or ous. The exceptions are the acids derived from ions with an ide suffix (see HCN in the preceding section). These acids undergo many reactions to form salts, compounds of a metal, and the ion of an acid. The ions from the acids H2S04 and HN03 are S042, N03. If an acid name has the suffix ic, the ion of this acid has a name with the suffix ate. If an acid name has the suffix ous, the ion has a name with the suffix ite. Salts have the same suffixes as the suffixes of the ions. The difference between the acid with a suffix ic and the acid with the suffix ous can many times be determined by visual inspection of the formula. The acid with the suffix ous usually has one fewer oxygen atom than the acid with the suffix ic. Examples ... 

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