Carboxylic acid derivatives summary

Addition-Elimination of Carboxylic Acid Derivatives Summary... 

A summary of nomenclature rules for carboxylic acid derivatives is given in Table 21.1. 

SUMMARY OF CARBOXYLIC ACID DERIVATIVE CHEMISTRY PREPARATION... 

The most important reactions of carboxylic acids are the conversions to various carboxylic acid derivatives, e.g. acid chlorides, acid anhydrides and esters. Esters are prepared by the reaction of carboxylic acids and alcohols. The reaction is acid catalysed and is known as Fischer esterification (see Section 5.5.5). Acid chlorides are obtained from carboxylic acids by the treatment of thionyl chloride (SOCI2) or oxalyl chloride [(COCl)2], and acid anhydrides are produced from two carboxylic acids. A summary of the conversion of carboxylic acid is presented here. All these conversions involve nucleophilic acyl substitutions (see Section 5.5.5). 

In summary, therefore, the detailed mechanism of the hydrolysis of carboxylic anhydrides is still in doubt and we must hope for further experimental evidence to clarify the position. As for the hydrolysis of the other carboxylic acid derivatives dealt with in this chapter, none of the mechanistic criteria, that have been used to interpret the kinetic data, gives an unambiguous interpretation, resulting in a situation where details of mechanism are open to argument. This is particularly the case for solvolysis reactions where uncertainty as to the structure and effect of the solvent preclude a firm assignment of transition state structures. This is not to say that the mechanisms are not... 

In summary, reductions of carboxylic acid derivatives to primary alcohols are usually accomplished by reaction of esters or acids with lithium aluminum hydride. The following equations provide several examples ... 

Summary Nomenclature of Carboxylic Acid Derivatives and Nitriles... 

The various carboxylic acid derivatives vary in their reactivity (stability of the leaving group). Acid chlorides, for example, are more reactive than anhydrides (don t leave as easily). A summary of the relative reactivities appears in Figure 12-32. 

Merzcr reports in his summary (1973) that rats metabolise chlortoluron to carboxylic acid derivatives. 

Carboxylic acids and carboxylic acid derivatives can also be prepared by methods other than nucleophilic acyl substitution reactions. A summary of the methods used to synthesize these compounds is given in Appendix IV. 

Carboxylic Acid Derivatives of Special Interest Summary of Reactions Summary Key Terms... 

Evans and coworkers have published an interesting study of the electrochemical behavior of a ferrocene-carboxylic acid derivative in the presence of BCD [18] and a summary of general guidelines on the electrochemical methodology that can be used to assess the complexation of redox-active molecules by cyclodextrin hosts [19]. However, the amphiphilic character of the surfactant viologens used in this work prevented us from applying most of these methods because the voltammetric... 

In Summary Nucleophilic attack on the carbonyl group of carboxylic acid derivatives is a key step in substitution by addition-elimination. Either acid or base catalysis may be observed. For carboxylic acids, the process is complicated by the poor leaving group (hydroxide) and competitive deprotonation of the acid by the nucleophile, acting as a base. With less basic nucleophiles, addition can occur. 

In Summary The relative electronegativity and the size of L in RCL controls the extent of resonance of the lone electron pair(s) and the relative reactivity of a carboxylic acid derivative in nucleophilic addition-elimination reactions. This effect manifests itself structurally and spectroscopically, as well as in the relative acidity and basicity of the a-hydrogen and the carbonyl oxygen, respectively. 

In Summary Acyl chlorides are attacked by a variety of nucleophiles, the reactions leading to new carboxylic acid derivatives, ketones, and aldehydes by addition-elimination mechanisms. The reactivity of acyl halides makes them useful synthetic relay points on the way... 

The oxidation of aldehydes (alkanals) and ketones (alkanones) has been reviewed extensively [1-3], and there are compilations based on reagent types [4-8] and oxidation methods for most functionalized compounds including those having carbonyl groups. Books [9, 10] and comprehensive review articles [11-16] on carboxylic acids and their derivatives also provide important background information on the oxidation of carbonyl compounds. This account will focus exclusively on the synthesis of carboxylic acid derivatives. After a brief summary of the well-estabHshed methods, new directions in oxidative transformations of carbonyl compounds will be described. Among these, in particular, catalytic [17, 18] and asymmetric versions will be emphasized. 

Brdnsted-Lowry theory, 194 contrast definitions, 194 indicators, 190 reactions, 188 titrations, 188 Acids, 183 aqueous, 179 carboxylic, 334 derivatives of organic, 337 equilibrium calculations, 192 experimental introduction, 183 names of common, 183 naming of organic, 339 properties of, 183 relative strengths, 192, 451 strength of, 190 summary, 185 weak, 190, 193 Actinides, 414 Actinium... 

Those polyester FBAs containing a benzoxazole group are usually prepared from the appropriate o-aminophenol and carboxylic acid (11.45 Y = OH) or one of its derivatives, as shown in Scheme 11.10. The reaction proceeds via an intermediate amide and it can be advantageous to start from an acid derivative such as the acid chloride (11.45 Y = Cl) or ester (11.45 Y = OEt), which are both more effective acylating agents. The preparation of compound 11.36, shown in Scheme 11.11, illustrates this process, but the optimum conditions for ring closure vary considerably from one structure to another. The article by Gold contains a valuable and detailed summary [4]. 

Figure 4.1 Summary of structural requirements for high teratogenic potency of carboxylic acids, a) Information obtained or derived from (50-58]. b) Esters of carboxylic...

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