How many stereoisomers of C4H8Br2 have structural isomers?

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Discussion Overview

The discussion revolves around identifying the structural isomers of the compound C4H8Br2, including considerations of chirality and stereocenters. Participants explore the number of structural isomers and the implications of stereochemistry.

Discussion Character

  • Homework-related
  • Debate/contested
  • Exploratory

Main Points Raised

  • One participant lists nine structural isomers of C4H8Br2, including various dibromobutane and dibromo-2-methylpropane compounds.
  • Another participant reminds that chirality should be considered in the discussion.
  • A participant argues that chirality does not affect the formula name since the bromine atoms are attached to different carbons.
  • There is a clarification that the focus is on structural isomers rather than stereoisomers.
  • Multiple participants inquire about the number of stereocenters, with some suggesting there are none, while others identify at least two stereocenters from the listed isomers.
  • One participant identifies four specific isomers that contain stereocenters and seeks confirmation from others.

Areas of Agreement / Disagreement

Participants express differing views on the presence and number of stereocenters in the structural isomers, indicating that the discussion remains unresolved regarding the exact count and implications of chirality.

Contextual Notes

There is uncertainty regarding the complete enumeration of structural isomers and the identification of stereocenters, as well as the implications of chirality on the naming of the compounds.

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Homework Statement


Name the structural isomers of C4H8Br2 and remember to number the carbon atoms such that you minimize the numbers in the name.

How many stuctural isomers of C4H8Br2 are there?

The Attempt at a Solution


I'm not sure how many there should be. So far I've found 9:
1,1-dibromobutane
1,2-dibromobutane
1,3-dibromobutane
1,4-dibromobutane
2,2-dibromobutane
2,3-dibromobutane
1,1-dibromo-2-methylpropane
1,2-dibromo-2-methylpropane
1,3-dibromo-2-methylpropaneAre there anymore that I'm missing? I can't seem to find them.
 
Last edited:
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Don't forget chirality.
 
I don't think chirality will affect the actual formula name anymore since I've taken care of all chiral forms by putting the Br atoms attached to different carbons.
 
Oh, you're right. Structural isormers, not stereoisomers.

In that case, I think you've got them all.
 
How many stereocentres are there?

0 correct?
 
ChemIsHard said:
How many stereocentres are there?

0 correct?

No, I see at least two from the list given.
 
1,2-dibromo-2-methylpropane
1,3-dibromo-2-methylpropane

Being the two? The stereocentre is on the first carbon in both cases right?

Sorry for the numerous questions, I'm just a little confused!
 
Make a model and try to superimpose 'em.
 
I found four to have stereocentres:
1,2-dibromobutane
1,3-dibromobutane
2,3-dibromobutane
1,2-dibromo-2-methylpropane

Can anyone confirm this?
 

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