Naming, acid anhydrides carboxylic acids

Given the IUPAC name of a carboxylic acid, salt, ester, amide, acyl halide, or anhydride, write its structural formula, and given the structure, write the name. 

Most anhydrides are named by dropping the word acid from the name of the carboxylic acid and then adding the word anhydride ... 

The name acid anhydride refers to the fact that you can generate a symmetrical acid anhydride by heating a pure sample of the corresponding carboxylic acid while removing the water that is produced ( anhydride " means without water"). An easier way to generate an acid anhydride is to mix an acid halide with a carboxylate anion, as shown below. 

In naming carboxylic acid anhydrides in which both acyl groups are the same we simply specify the acid and replace acid by anhydride When the acyl groups are dif ferent they are cited m alphabetical order... 

Unsymmetrical anhydrides—those prepared from two different carboxylic acids—are named by citing the two acids alphabetically and then adding anhydride. 

Acid anhydride, amides from, 807 eleclrostatic potential map of, 791 esters from, 807 from acid chlorides, 806 from carboxylic acids, 795 1R spectroscopy of, 822-823 naming, 786... 

Methods for the A-acylation of similar heterocycles, such as simple thiazolidinethiones, have been reported since 1977, namely acyl chlorides in miscellaneous conditions,586 or carboxylic acids under DCC-activation.60,61 However the easiest and most effective method involves acyl chlorides or carboxylic anhydrides in the presence of an amine.47 Applying that procedure on carbohydrate scaffolds Rollin and co-workers62 reported the synthesis of diverse /V-acylated OZTs. The reactions were performed with good yields and the /V-selective acylation was ascertained by NMR— namely the thiocarbonyl 13C chemical shift (Scheme 41). Thanks to the dual nature of the carbanion drifting in the reaction,596 60 no competitive formation of the thioester, as mentioned by Plusquellec el al. in the case of benzothiazole, was observed. 

Commercially available hyperbranched polymer, a poly(ester-amide) is currently being marketed by DSM under the product name Hybrane [13] (Figure 8.2). It is also a hydroxyl-functionalized product, but contains both amide and ester linkages. The synthesis is accomplished in two steps cyclic anhydrides are reacted with diisopropanolamine to give an amide-intermediate, possessing two hydroxyl groups and one carboxylic acid. The subsequent polymerization takes places via an oxazolinium intermediate which results in the formation of a... 

The name, maleic anhydride, came about in the same fashion. as any number of compounds early in the petrochemical Business Many organic acids and their derivatives were given common names based on some early observations, their special source in nature, or on some special feature of their structure. MA was first isolated in the 1850—75 era by dehydration of malic acid, a sugar acid found in apple juice. The Latin word for apple is malum. Hence, malum, malic, maleic. The suffix, anhydride, which follows each alias of MA, has a simple definition a compound derived by the loss of a molecule of water from two carboxyl groups (-COOH). 

Pyridine is often used as a solvent in such reactions, since it is also fnnctions as a weak base. As an aromatic base, pyridine will promote ionization of the carboxylic acid to carboxylate, and also react with the other product of the reaction, namely HCl. Withont removal of HCl, the anhydride formed might be hydrolysed under the acid conditions generated. 

The name anhydride means without water, so that makes it pretty clear that the general idea behind the formation of an acid anhydride is to remove water from a carboxylic acid. Both acyl chlorides and acid anhydrides are very effective at removing water. In some cases, heat can be used to remove water. 

The nomenclature for this homologous series is somewhat confused. The term PANs has been used historically to denote peroxyacyl nitrates, and this terminology continues to be used extensively in the literature, despite the lack of adherence to traditional IUPAC rules of nomenclature. Because the PANs can be considered to be mixed anhydrides of carboxylic acids and nitric acid, another suggestion (Roberts, 1990) has been peroxyacetic nitric anhydride for CH,C(0)00NO2 and peroxy carboxylic nitric anhydrides for the whole class of compounds. Although it does not follow the IUPAC rules, it would be consistent with the widespread use of the name PAN but also reflect the structure more accurately. Table 6.20 shows the structures and commonly used names of some PANs that have been observed in the atmosphere and/or in laboratory studies. 

Carboxylic acids and their derivatives like esters, amides, anhydrides, and acyl halides are formally synthesized from olefins, carbon monoxide, and compounds represented by Nu-H such as H2O, ROH, RNH2, RCOOH (Equations (4) and (5)). Alkynes also react under similar conditions to afford the corresponding unsaturated carboxylic acid derivatives. These reactions have been named hydrocarboxylation, hydroalkoxycarbonylation, and hydroaminocarbonylation. 

Symmetrical acid anhydrides are named by replacing the -acid suffix of the parent carboxylic acids with the word anhydride. Mixed anhydrides that consist of two different acid-derived parts are named using the names of the two individual acids with an alphabetical order. 

Acid anhydrides, as their name implies, are formed from the dehydration reaction of two carboxylic acid groups (Fig. 72). Anhydrides are highly reactive toward nucleophiles and are able to acylate a number of the important functional groups of proteins and other macromolecules. Upon nucleophilic attack, the anhydride yields one carboxylic acid for every acylated product. If the anhydride was formed from monocar-boxylic acids, such as acetic anhydride, then the acylation occurs with release of one carboxylate group. However for dicarboxylic acid anhydrides, such as succinic anhydride, upon reaction with a nucleophile the ring structure of the anhydride opens, forming the acylated product modified to contain a newly formed carboxylate group. 

Alternative reactions employ coupling reagents such as DCC (Steglich Esterification), preformed esters (transesterification), carboxylic acid chlorides or anhydrides. These reactions avoid the production of water. Another pathway for the production of esters is the formation of a carboxylate anion, which then reacts as a nucleophile with an electrophile (similar reactions can be found here). Esters may also be produced by oxidations, namely by the Baeyer-Villiger oxidation and oxidative esterifications. 

The first reagent combination, carboxylic acid chloride/A1C13, reacts via the A1C13 complex A of the acid chloride or via the acylium tetrachloroaluminate B formed from it by /)-elimination. A carboxylic acid anhydride and A1C13 react via analogous electrophiles, namely via the A1C13 complex D of the anhydride or via the acylium salt E formed therefore by a /T elimination. The protonated anhydride F and the protonated carboxylic acid C are the reactive electrophiles of the Friedel-Crafts acylations catalyzed by Bronsted acids. 

Name an aromatic compound, a phenol, an aldehyde, a ketone, a carboxylic acid, an acid chloride, an anhydride, an ester, an amide, a nitrile, and a carboxylic acid salt. (Problems 12.21, 12.31, and 12.33)... 

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