Nomenclature acyl halides

The nomenclature of acyl halides is simple. Their names are deduced from the name of the constituent acid with the suffix -yl or -oyl and the name of the halide. 

As mentioned in Section 19-9, esters, RCOR, constitute perhaps the most important class of carboxylic derivatives. They are particularly widespread in nature, contributing especially to the pleasant flavors and aromas of many flowers and fruits. Esters undergo typical carbonyl chemistry but with reduced reactivity relative to that of either acyl halides or carboxylic anhydrides. This section begins with a discussion of ester nomenclature. Descriptions follow of the transformations that esters undergo with a variety of nucleophilic reagents. 

In this chapter, we will be discussing the chemistry of carboxylic acids, esters, acyl halides, anhydrides, and amides. This is dominated by substitution, where one group is exchanged with another. Substitution is NOT possible for aldehydes and ketones, as you can t displace H or — they are hopeless leaving groups. First, let s review some nomenclature. The suffix for carboxylic acids is -oic acid and the carbonyl of the acid is always numbered as C-1. The acid takes precedence over most other functional groups. Some examples are shown in Figure 15.1. Notice that when we have both a ketone and an acid in the molecule, it is named as a carboxylic acid, and the ketone is described as oxo. ... 

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. 

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