Acyl chlorides nomenclature

This chapter concerns the preparation and reactions of acyl chlorides acid anhydrides thioesters esters amides and nitriles These com pounds are generally classified as carboxylic acid derivatives and their nomenclature is based on that of carboxylic acids... 

In Chapter 9 you see the basic structure of each of the carboxylic acids and Ccirboxylic acid derivatives. In this chapter we focus on the carboxylic acids and related compounds, such as esters, acyl chlorides, and acid anhydrides, and we also include some information on amides (see Chapter 13 for an additional examination of cimides). Before you can get into synthesis and reactions, though, you need to understand the structure and nomenclature of these compounds. 

When the hydroxyl is replaced by chlorine, an acyl chloride is obtained R-C-Cl. The nomenclature of an acyl... 

Recently, a three-component 1,2,4-triazole synthesis involving Nef-Huisgen cascade was developed." Thus addition of acyl chloride 22 to isocyanide 23 (Nef reaction) generated the imidoyl chloride [nomenclature... 

The nomenclature of this class of compounds is not at all clear. For example, the following names can be found in the literature hydroxamic acid chlorides, hydroxamic chlorides, hydroximic chlorides (Beilstein lists them as Hydroximsaure chloride ), and acyl and aroylchloride oximes. The latter names are used by Chemical Abstracts, Although the name benzoyl chloride oxime for benzhydroxamoyl chloride is formally correct, it does not reflect the close relationship between hydroxamoyl chlorides and hydroxamic acids, their hydrolysis products. In order to be consistent with the nomenclature used in the earlier chapters, I prefer the term hydroxamoyl to hydroxamic chloride. The interrelationship of the halides with the corresponding acids is shown below, and R is representative of the alkyl, aryl, acyl, aroyl, and carbalkoxy group. 

This chapter will revisit the lUPAC nomenclature system for aldehydes, ketones, and carboxylic acids, as well as introduce nomenclature for the four main acid derivatives acid chlorides, anhydrides, esters, and amides. The chapter will show the similarity of a carbonyl and an alkene in that both react with a Br0nsted-Lowry acid or a Lewis acid. The reaction of a carbonyl compound with an acid will generate a resonance stabilized oxocarbenium ion. Ketones and aldehydes react with nucleophiles by what is known as acyl addition to give an alkoxide product, which is converted to an alcohol in a second chemical step. Acid derivatives differ from aldehydes or ketones in that a leaving group is attached to the carbonyl carbon. Acid derivatives react with nucleophiles by what is known as acyl substitution, via a tetrahedral intermediate. 

Many authors include these reactions among acylations, based on the similarity of the processes and the nomenclature of some reagents, for example from picric acid (13) one prepares picryl chloride which yields a picramide according to equation (18). 

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