Carbonyl compounds carboxylic acids and derivatives

Carboxylic acids (RCO2H) are members of a class of acyl compounds which aU contain an electronegative group bonded to RCO. 

RCONH2 is a primary amide, RCONHR is a secondary anude, and RCONR2 is a tertiary amide 

Keynotes in Organic Chemistry, Second Edition. Andrew F. Parsons. 

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REDUCTION OF CARBONYL COMPOUNDS, CARBOXYLIC ACIDS AND THEIR DERIVATIVES... 

See also page 403, Section 6, for the synthesis of a,/3-unsaturated nitriles, carboxylic acids and derivatives, and page 1711, Section 4, for the homologation of carbonyl compounds. 

D. W Boykin and A. L. Baumstark, 170 NMR spectroscopic data for carbonyl compounds I. Aldehydes and ketones II. Carboxylic acids and derivatives, in 17O NMR Spectroscopy in Organic Chemistry, D. W. Boykin, ed., CRC Press, Boca Raton, 1991. 

Like all carbonyl compounds, carboxylic acid derivatives have a strong C=0 absorption between 1600 and 1850 cm. ... 

Acyl compounds—carboxylic acids and their derivatives—typically undergo nucleophilic substitution in which —OH, —Cl, —OOCR, —NH2, or —OR is replaced by some other basic group. Substitution takes place much more readily than at a saturated carbon atom indeed, many of these substitutions do not usually take place at all in the absence of the carbonyl group, as, for example, replacement of-NHjby-OH. 

Most information on cyclocondensation reactions of ZV-aminoazoles is concerned with vicinal N.C-diaminoazoles. In most cases, reactions were carried out with various carbonyl-containing compounds carboxylic acids and their derivatives, aldehydes and ketones, 1,2- an 1,3-dicarbonyl compounds, etc. Depending on the structure of these synthons, cyclocondensations lead to the formation of five-, and six- or seven-membered heterocycles. 

Primary and secondary alcohols (e.g., cyclohexanol) add to the carbon of the carbonyl of carboxylic acids and compounds derived from carboxyUc acids to form... 

Participation of fluorocarbocations, derived from carboxylic acids and from halo acetones, in reactions of carbonyl compounds with sulfur tetrafluoride has been directly evidenced by trapping them with aromatic hydrocarbons [207, 20S],... 

In this period, the most important reactions of the isocyanides were the formations of tetrazole derivatives from isocyanides and hydrazoic acid, a process introduced in 1910 by Oliveri-Mandala and Alagna, and then in 1921 Passerini introduced the reaction (P-3CR), which was the first 3-component reaction of the isocyanides. In the 1940s Baker,and later Dewar, proposed mechanisms of the P-3CR. The important role of the intermediate hydrogen bond between the carboxylic acid and the carbonyl compound in suitable solvents was mentioned. ... 

Carbonylation is one of the most important reactions leading to C-C bond formation. Direct synthesis of carbonyl compounds with CO gives rise to carboxylic acids and their derivatives, such as esters, amides, lactones, lactams etc. The process can be represented by the simple reactions of Scheme 5.1. 

Types of compounds are arranged according to the following system hydrocarbons and basic heterocycles hydroxy compounds and their ethers mercapto compounds, sulfides, disulfides, sulfoxides and sulfones, sulfenic, sulfinic and sulfonic acids and their derivatives amines, hydroxylamines, hydrazines, hydrazo and azo compounds carbonyl compounds and their functional derivatives carboxylic acids and their functional derivatives and organometallics. In each chapter, halogen, nitroso, nitro, diazo and azido compounds follow the parent compounds as their substitution derivatives. More detail is indicated in the table of contents. In polyfunctional derivatives reduction of a particular function is mentioned in the place of the highest functionality. Reduction of acrylic acid, for example, is described in the chapter on acids rather than functionalized ethylene, and reduction of ethyl acetoacetate is discussed in the chapter on esters rather than in the chapter on ketones. 

In Part 111 we cover that broad category of organic compounds called the carbonyls. First we give you an overview of Ccirbonyl basics, including structure, reactivity, and spectroscopy. Then we go into more detail on aldehydes and ketones, enols and enolates, and carboxylic acids and their derivatives. 

The carbonyl stretch in the 1,700 cm region of the infrared spectra of carbonyl compounds is a very obvious feature of the spectrum for these compounds, in this section we look at some other spectral features of carboxylic acids and their derivatives, and also at some chemical tests that can help you determine what you re dealing with. 

Formation of carboxylic acids and their derivatives. Aryl and alkenyl halides undergo Pd-catalyzed carbonylation under mild conditions, offering useful synthetic methods for carbonyl compounds. The facile CO insertion into aryl- or alkenylpalladium complexes, followed by the nucleophilic attack of alcohol or water affords esters or carboxylic acids. Aromatic and a,/3-unsaturated carboxylic acids or esters are prepared by the carbonylation of aryl and alkenyl halides in water or alcohols[301-305]. 

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