I'm afraid I can't find an image for this organic compound, but when applying lowest locant rule in the numbering (1-methylethenyl) gets 2 and Cl gets 4. (2,4) is less than (3,5). Why then is lowest locant rule not applied here? Also here (1-methylethenyl) is an alkene, and isn't priority order of alkenes before halogens which have no priority?


1 Answer 1


The most important simplified criteria for the numbering are:

  1. lower locants for the group that is expressed as suffix
  2. lower locants for multiple bonds
  3. lower locants for prefixes
  4. lower locants for substituents cited first as a prefix in the name

The corresponding actual wording in the current version of Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) reads as follows:


When several structural features appear in cyclic and acyclic compounds, low locants are assigned to them in the following decreasing order of seniority:


(c) principal characteristic groups and free valences (suffixes);


(e) saturation/unsaturation:

  (i) low locants are given to hydro/dehydro prefixes (…) and ‘ene’ and ‘yne’ endings;

  (ii) low locants are given first to multiple bonds as a set and then to double bonds (…);

(f) detachable alphabetized prefixes, all considered together in a series of increasing numerical order;

(g) lowest locants for the substituent cited first as a prefix in the name;


The principal characteristic group of the compound that is given in the question is the $\ce{-OH}$ group. It is expressed as the suffix “-ol”. According to Rule (c), a low locant is assigned first to this group, i.e. “-1-ol”.

In the next step, low locants are assigned to the double bonds according to Rule (e), i.e. “cyclopenta-1,3-dien-1-ol”.

That leaves only one possible locant set for the remaining substituents, i.e. “3-chloro” and “5-(prop-1-en-2-yl)”. The rules (f) and (g) are not needed to make a decision.

Therefore, the complete name for the compound that is given in the question is 3-chloro-5-(prop-1-en-2-yl)cyclopenta-1,3-dien-1-ol.


Note that the preferred prefix for the “isopropenyl” or “1-methylethenyl” (completely: “1-methyleth-1-en-1-yl”) is now “prop-1-en-2-yl”.


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