IUPAC nomenclature for many multiple bonds

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Discussion Overview

The discussion revolves around the IUPAC nomenclature rules for organic compounds with multiple bonds, specifically the prioritization of double versus triple bonds in numbering carbon chains. Participants express confusion regarding the correct application of these rules when both types of bonds are present in a molecule.

Discussion Character

  • Debate/contested
  • Conceptual clarification

Main Points Raised

  • One participant states that their previous teacher taught that double bonds take precedence over triple bonds in numbering, while their current teacher suggests that the lowest number should be assigned to whichever multiple bond is closest to the end of the chain.
  • Another participant refers to the "lowest sum of locants" rule as a guideline for numbering when multiple bonds are present.
  • Some participants suggest checking the IUPAC website for definitive rules rather than relying on informal sources.
  • There is mention of the IUPAC site redirecting to ACD Labs ChemSketch pages as a source of nomenclature rules, although it is noted that the most current rules may only be available in print due to copyright issues.
  • One participant emphasizes the importance of consulting original sources for accurate information rather than seeking opinions from others.

Areas of Agreement / Disagreement

Participants express differing views on the correct approach to numbering carbon atoms in the presence of multiple bonds, indicating that there is no consensus on the matter. Some advocate for the double bond's priority, while others support the lowest locants rule.

Contextual Notes

There are references to potential changes in IUPAC rules over time and the limitations of accessing the most current nomenclature guidelines due to copyright restrictions.

donaldparida
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My previous Chemistry teacher while teaching IUPAC nomenclature said that the double bond is always given greater priority over the triple bond and the numbering of the carbon atom chain is done in such a way that the double bond gets the lowest possible number while my present Chemistry teacher says that the numbering of the carbon atoms is done in such a way that the multiple bond gets the lowest number whether it is the double bond or the triple bond (whichever multiple bond is nearest to the end when both the ends are considered, numbering is done from that end).

On surfing through the various sites on the Internet, i came across the lowest sum of locants rule.

I am confused and cannot understand how to number the carbon atoms for IUPAC nomenclature purposes when many multiple bonds are present in the molecule. What is the actual rule?
 
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Very general remark: why don't you try to find IUPAC rules on the IUPAC site to check the source, instead of asking random people on the random site?

If memory serves me well at some point in time IUPAC site was redirecting to the ACD Labs ChemSketch pages as the definitive source, still, that meant it WAS the definitive source.
 
Borek said:
Very general remark: why don't you try to find IUPAC rules on the IUPAC site to check the source, instead of asking random people on the random site?

If memory serves me well at some point in time IUPAC site was redirecting to the ACD Labs ChemSketch pages as the definitive source, still, that meant it WAS the definitive source.

As the disclaimer on the ACD Labs webpage mentions the current nomenclature rules (2013) is present only in print form due to copyright issues. I don't know how much has changed but I don't think it'll matter to us students.
 
No matter what the situation is (I admit I have not checked) it doesn't change fact that it is best to consult the original source instead of asking for opinions. That's all I tried to say.
 
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