Which Product Won't Be Obtained in a Wurtz Reaction?

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SUMMARY

The discussion centers on the Wurtz reaction and the identification of products that can be formed. Participants conclude that the major product will be (a), while (d) will not be obtained. The conversation highlights the importance of understanding free radical and ionic mechanisms, as well as the resonance stability of allyl radicals. A key resource shared includes a link to a Master Organic Chemistry article that explains the molecular orbitals of allyl ions and radicals.

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  • Understanding of Wurtz reaction mechanisms
  • Knowledge of free radical and ionic mechanisms in organic chemistry
  • Familiarity with resonance structures and stability of radicals
  • Basic concepts of frontier molecular orbital theory
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  • Learn about resonance structures of allyl radicals and ions
  • Explore frontier molecular orbital theory and its applications
  • Research the implications of radical stability in organic reactions
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baldbrain
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Homework Statement


Which one of the following products will not be obtained in the given Wurtz reaction?
IMG_20181130_195951.JPG

The Attempt at a Solution


Well, (a) will definitely be the major product. We know that this reaction may proceed by a free radical or an ionic mechanism. But what's that got to do with the C-14 shifting position inside the ring? Any help?
 

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It might help to draw out the resonance structures of the radical/ionic intermediate.
 
TeethWhitener said:
It might help to draw out the resonance structures of the radical/ionic intermediate.
Well, won't that conversion require additional energy? Do we presume it is available?
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baldbrain said:
Well, won't that conversion require additional energy?
Why? Maybe draw the hydrogens explicitly.
 
TeethWhitener said:
Why? Maybe draw the hydrogens explicitly.
What difference does that make? Won't THIS ##\downarrow## require additional energy?
IMG_20181130_210412.jpg
 

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baldbrain said:
Won't THIS ↓↓\downarrow require additional energy?
Google "allyl radical."
 
TeethWhitener said:
Google "allyl radical."
****, you're right...I keep forgetting that.
 
I don't know why, but I still don't have a keen eye spotting the allyl radical. Get me?
 
  • #10
You might remember I stumbled upon this 'allyl' thingy even in that "same SN1 & SN2 product" problem.
Anyway, Thanks again.:smile:
 
  • #11
baldbrain said:
I don't know why, but I still don't have a keen eye spotting the allyl radical.
It's not a bad idea to have the possibility of allylic resonance in the back of your mind whenever you see a double bond. Other than that, I'm not sure there are any tricks to remembering it.
 
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  • #12
I forgot to mention that the answer would be (d). You might've already guessed that.
 
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