Name the following molecule (common name and IUPAC)?

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    Iupac Molecule
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Discussion Overview

The discussion revolves around the naming of organic molecules, specifically focusing on the common and IUPAC names for a given structure. Participants explore the implications of using traditional nomenclature such as "sec-", "iso-", and "tert-" in comparison to IUPAC naming conventions.

Discussion Character

  • Debate/contested
  • Technical explanation
  • Conceptual clarification

Main Points Raised

  • One participant identifies molecule #1 as sec-pentylcyclohexane and seeks the name for molecule #2.
  • Another participant suggests the name 3-pentylcyclohexane as a possible IUPAC name.
  • Questions arise regarding the applicability of iso-, sec-, and tert- nomenclature for the discussed molecules.
  • A participant challenges the initial identification of sec-pentylcyclohexane, prompting further clarification.
  • Concerns are raised about the ambiguity of the term sec-pentylcyclohexane, as it could refer to substitutions at either the 2 or 3 position on the cyclohexane ring.
  • One participant argues that traditional nomenclature is less useful for larger carbon chains due to the complexity and potential for confusion.
  • Another participant expresses the need to understand iso-, sec-, and tert- names for exam purposes, indicating a preference for these terms in certain contexts.
  • There is a discussion about the ambiguity of sec-pentylcyclohexane compared to sec-butylcyclohexane, which is viewed as unambiguous.
  • Participants note that the traditional names can lead to miscommunication and suggest that IUPAC names are more precise.

Areas of Agreement / Disagreement

Participants express differing views on the usefulness and clarity of traditional nomenclature versus IUPAC naming. There is no consensus on the best approach to naming the molecules discussed, and the ambiguity of certain terms remains a point of contention.

Contextual Notes

Participants highlight that the use of sec-, iso-, and tert- names can lead to confusion, especially with larger carbon chains, and that these terms may not be well-defined in all contexts. The discussion reflects the complexity of organic nomenclature and the challenges in achieving clarity.

oferon
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http://img43.imageshack.us/img43/2916/95953925.jpg

I understand molecule #1 is sec-pentylcyclohexane
But how would you call molecule 2?

Please give common and IUPAC names (no need for too much detailed explanations)
Thank you.
 
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any iso/sec/tert name for it?
 
oferon said:
http://img43.imageshack.us/img43/2916/95953925.jpg

I understand molecule #1 is sec-pentylcyclohexane

No you don't. Try again.
 
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Why not?
Here is sec-butylcyclohexane:
cas7058-01-7.gif


And another carbon to the chain simply makes it pentyl, am I wrong?
 
Here is http://www.chemindustry.com/chemicals/0330843.html and http://www.chemindustry.com/chemicals/0434357.html.

sec-pentyl(stuff) isn't well-defined.
 
yes, the two systems are 2-pentylcyclohexane and 3-pentylcyclohexane.

These are both common and IUPAC names.

The sec- iso- tert- type names are confusing and only really useful for industrial compounds commonly known by these names or chains of 4 or fewer carbon atoms. For pentyl systems, the traditional nomenclature is even more confused by the intrusion of "amyl"

"Common" or "industrial" names are not really worth knowing these days unless you are working with shipments of stuff. There are about 20 isomers of octane. n-octane is the straight chain isomer. There is no possible way you could know without looking it up or working with it that iso-octane is 2,2,4-trimethylpentane!
 
I would need to know iso, sec and tert for my exam.. Some answers you should pick appear as iso\sec\tert rather than IUPAC formal names.. I wish it wasn't like that
 
I think you'll find that where you are presented 'sec-' or 'tert-' substituted alkanes there will be only one obvious answer. Sec-butylcyclohexane is unambiguous since the cyclohexyl substitution at either secondary carbons results in a single product. That isn't the case with sec-pentylcyclohexane. Substitution at either the 2 or the 3 position is correct for that name so the ambiguity resulting from that nomenclature will result in misidentification or miscommunication and shouldn't be used.

BTW, a typical test question reads, "The name sec-butyl alcohol defines a specific structure but the name sec-penty alcohol is ambiguous. Explain."

So now you know.
 
  • #10
chemisttree said:
I think you'll find that where you are presented 'sec-' or 'tert-' substituted alkanes there will be only one obvious answer. Sec-butylcyclohexane is unambiguous since the cyclohexyl substitution at either secondary carbons results in a single product. That isn't the case with sec-pentylcyclohexane. Substitution at either the 2 or the 3 position is correct for that name so the ambiguity resulting from that nomenclature will result in misidentification or miscommunication and shouldn't be used.

BTW, a typical test question reads, "The name sec-butyl alcohol defines a specific structure but the name sec-penty alcohol is ambiguous. Explain."

So now you know.

Tongue in cheek and only very marginally relevant to the OP question :-

Another test question: "The name sec-butyl alcohol does not unambiguously define a single substance. Nor does the IUPAC designation 2-butanol. Explain why not, and how to rectify the nomenclature."
 

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