Carboxylic acids qualitative/quantitative analyses

Synthetic operations involving ozonolysis lead to formation of aldehydes, ketones or carboxylic acids, as shown in Scheme 16, or to various peroxide compounds, as depicted in Scheme 7 (Section V.B.5), depending on the nature of the R to R substituents and the prevalent conditions of reaction no effort is usually made to isolate either type of ozonide, but only the final products. This notwithstanding, intermediates 276 and 278 are prone to qualitative, quantitative and structural analysis. The appearance of a red-brown discoloration during ozonization of an olefin below — 180°C was postulated as due to formation of an olefin-ozone complex, in analogy to the jr-complexes formed with aromatic compounds however, this contention was contested (see also Section V1I.C.2). 

Ozone, while somewhat inconvenient to use, is way qiecific in its reactions with alkenes. It is widely employed for selective synthesis, for qualitative and quantitative analysis of unsaturated compounds, and for studying the position of double bonds in macromolecules. The nature of the products obtained from ozonolysis reactions is determitted by the way in which the reaction is carried out Different workup procedures (hydrolytic, reductive or oxidative) can be used to produce alcohols, aldehydes, ketones, carboxylic acids or esters. 

A very comprehensive analysis of hydrocarbons (linear, acyclic and cyclic - steranes, hopanes etc.- isoprenoids) carboxylic acids, aldehydes, ketones and amines of the Vale do Paraiba and Marau oil shales was made by Chicarelli (27). An extremely careful quantitative and qualitative analysis of hydrocarbons (n-, iso-and anteiso-paraffins, isoprenoids, steranes and triterpanes) and carboxylic acids of Irati oil shale was presented by Carvalhaes (28). Nooner Oro (29) also reported data on the hydrocarbons pres ent in the Irati Formation. Polycyclic aromatic hydrocarbons in I-rati were determined by Youngblood Blumer (40). 

In Section IV.B we will discuss the ortho-effect of NO2 as manifested in the ionization of carboxylic and other acids and (in Section IV.C) in the reactions of substituted benzoic acids with diazodiphenylmethane (DDM). Only in the case of the latter system can really satisfactory correlation analysis be taken as the basis for discussion. For most of the other systems discussion will have to be qualitative or, at best, semi-quantitative. 

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