The following structure represents the compound cyclohexylbenzene:


Why can't the benzene ring be treated as a substituent and the compound be called benzylcyclohexane?

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    $\begingroup$ There is no benzyl there, just phenyl. $\endgroup$ – Poutnik Nov 23 '20 at 6:24
  • $\begingroup$ First of all see the comment above. Then, consider that the "why" where dealing with nomenclature is always a rule. Studying the chemistry of cyclohexane, your proposal would be appropriate and reasonable. But imagine someone searching for your work. S/he would have to look for two different options.... In other words, plenty virtual infinite examples like that exist. Nomenclature is needed to uniquely determine what is what in a general homogenous way readable by all. $\endgroup$ – Alchimista Nov 23 '20 at 8:46
  • $\begingroup$ And even with nomenclature on place, there exist accepted or tolerated names, either for historical reasons or because belongs to different systems of rules. $\endgroup$ – Alchimista Nov 23 '20 at 9:58
  • $\begingroup$ Same size rings, the one with more double bonds is the parent. But it is phenylcycloheptane where 7>6. $\endgroup$ – user55119 Nov 23 '20 at 20:56

The relevant rule for the seniority order of parent structures in the current version of Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) reads as follows.


P-44.4.1 If the criteria of P-44.1 through P-44.3, where applicable, do not effect a choice of a senior parent structure, the following criteria are applied successively until there are no alternatives remaining. These criteria are illustrated in P- through P-
The senior ring, ring system, or principal chain:
(a) has the greater number of multiple bonds (P-;

P- The senior ring, ring system or principal chain has the greater number of multiple bonds; for the purpose of this criterion, mancude rings or ring systems are considered as consisting of noncumulative double bonds [criterion (a) in P-44.4.1].

Therefore, the name of the compound that is given in the question is cyclohexylbenzene rather than “phenylcyclohexane” since benzene has more multiple bonds than cyclohexane.

Note that this rule is not to be confused with the rules for systems composed of rings and chains, which are less strict. For systems composed of rings and chains, the context may favor the ring or the chain; nevertheless, the ring is selected as the parent structure for the preferred IUPAC name. In case of cyclohexylbenzene, however, benzene is always the parent structure – not only for the preferred IUPAC name.


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