Drawing 1-bromo-6-chlorodispiro [2.1.2^5.1^3] octane

In summary, the conversation discusses confusion over two possible compounds for a specific nomenclature. Both compounds have the same name when plugged into an online IUPAC namer, but upon further examination, they are distinct compounds. The correct compound is determined by following the IUPAC guidelines and considering the lower locant. To differentiate between the two compounds, a cis/trans convention or the absolute chiral configuration can be used.
  • #1
Sunwoo Bae
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Homework Statement
The nomenclature for a compound is given: 1-bromo-6-chlorodispiro [2.1.2^5.1^3] octane
Draw the structure of this compound
Relevant Equations
none
1618413891884.png

I tried drawing the structure, and I do not know which one of the two is the correct compound for the nomenclature.
Which one would be the correct one, and why?

Thank you!
 
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  • #2
First of all, kudos to you for getting the right ring structure! Polycyclic IUPAC conventions caused me no end of headaches in school.

Actually answering your question is a bit tricky. If you, for instance, plug both formulas into an online IUPAC namer, you get the same name for both compounds. However, if you actually look at models of the two, you see that they are in fact distinct compounds. This means you have to go to the source IUPAC documents for the answer. I found one of relevance here (possibly paywalled):
https://www.degruyter.com/document/doi/10.1351/pac199971030531/html
See section SP-9 in the link above. The numbering always goes to the lower locant. So both compounds are in fact 1-bromo-6-chloro. To distinguish them, per the document above, a cis/trans convention is used (apparently E and Z are only used for double bonds). Alternatively, you can determine the absolute chiral configuration (R vs. S) at the 3 and 5 carbons.
 
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FAQ: Drawing 1-bromo-6-chlorodispiro [2.1.2^5.1^3] octane

What is the chemical structure of 1-bromo-6-chlorodispiro [2.1.2^5.1^3] octane?

The chemical structure of 1-bromo-6-chlorodispiro [2.1.2^5.1^3] octane is a complex compound with a spiro structure, meaning it has two rings connected at a single atom. It also contains a bromine atom and a chlorine atom attached to different carbon atoms in the structure.

What is the molecular formula of 1-bromo-6-chlorodispiro [2.1.2^5.1^3] octane?

The molecular formula of 1-bromo-6-chlorodispiro [2.1.2^5.1^3] octane is C10H14BrCl.

What are the physical properties of 1-bromo-6-chlorodispiro [2.1.2^5.1^3] octane?

1-bromo-6-chlorodispiro [2.1.2^5.1^3] octane is a colorless liquid with a boiling point of approximately 180-185°C and a melting point of around -20°C. It is insoluble in water but soluble in organic solvents.

What are the uses of 1-bromo-6-chlorodispiro [2.1.2^5.1^3] octane?

1-bromo-6-chlorodispiro [2.1.2^5.1^3] octane is used as a reagent in organic synthesis, particularly in the formation of spiro compounds. It can also be used as a starting material for the synthesis of other chemical compounds.

Is 1-bromo-6-chlorodispiro [2.1.2^5.1^3] octane hazardous?

Yes, 1-bromo-6-chlorodispiro [2.1.2^5.1^3] octane is considered hazardous and should be handled with caution. It is flammable and may cause skin and eye irritation. Proper safety precautions should be taken when handling this compound.

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