From The need for good nomenclature by Edward W. Godly:
[T]he IUPAC ‘Blue Book’ rules are something of a patchwork quilt. It is intended to cover the entire bed of Organic Chemistry although some parts are covered more than once.
Even if a beautifully simple and appealing new system were devised and promulgated now, it would not result in immediate abandonment of existing procedures nor even a gradual supplanting of them. An attempt was made to re-think the whole approach to systematic nomenclature following the discernment by the author of a lack of logicality in the patchwork of revision and extension to organic nomenclature over the past 200 years. This is the so-called HIRN system, the principles for which were published in 1984. Its author claims it to be simple, logically consistent and to use far fewer rules than those of IUPAC. So far, it has not won many converts and this characterizes the general attitude to chemical nomenclature, even among chemists, i.e. almost total lack of interest.
The mid-century devising of line notations was seen as a liberation from all the complexity of systematic naming. Unfortunately, the Wiswesser Line Notation — the one which most widely caught on — requires mastery of a set of encoding and decoding rules filling well over 200 pages of an instruction manual. The system is easy to apply in the sense that playing the violin is easy; in other words the required facility is achieved only by constant practice.
It probably comes as a shock to discover that the rules do not constitute a beginner’s instruction manual but are couched in terse language and require months if not years of study and practice before a fairly complicated molecule can be tackled with confidence. A commonplace reaction is to riffle through the Blue Book looking for an example that looks fairly close to the molecule in question and try to name it by analogy.
I tried to meet certain aspects of this demand by writing a stand-alone instruction manual on naming new organic compounds. <...> Initial trials on user panels gave promising results, the only failures being due to certain subjects inserting bits of their own knowledge instead of blindly following the instructions.
