Rules for IUPAC names of polyfunctional organic compounds
Organic elements which have two or more functional groups are called polyfunctional compounds. Their IUPAC names are obtained as follows,
(i) Principal functional group : If the organic compound contains two or more functional groups, one of the functional sets is selected as the principal functional group while all the remaining functional groups (also called the secondary functional groups) are treated as substituents. The following order of preference is used while selecting the principal functional group.
Sulphonic acids > carboxylic acids > anhydrides > esters > acid chlorides > acid amides > nitriles > aldehydes > ketones > thiols > alcohols >alkenes > alkynes.
All the remaining functional sets such as halo (fluoro, chloro, bromo, iodo), nitroso (-NO), -nitro (-NO2), amino (-NH2) and alkoxy (-OR) are treated as substituents.
(ii) Selecting the principal chain : Select the longest continuous chain of carbon atoms containing the principal functional group and maximum number of secondary functional groups and multiple bonds, if any.
(iii) Numbering the principal chain : Number the principal chain in such a way that the principal functional group gets the lowest possible number followed by double bond and triple bond and the substituents, i.e.
Principal functional set > double bond > triple bond > substituents
(iv) Alphabetical order : Identify the prefixes and the positional numbers (also called locants) for the secondary functional groups and other substituents and place them in alphabetical order before the word root.
(3) Polyfunctional compounds containing more than two like functional groups : According to latest convention (1993 recommendations for IUPAC nomenclature), if an unbranched carbon reaction chain is directly linked to more than two like functional sets, the organic element is called as a derivative of the parent alkane which does not include carbon atoms of the functional sets. As given,
Following the above rule, citric acid may be named as,
2-Hydroxypropane-1, 2, 3-tricarboxylic acid
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