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

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Discussion Overview

The discussion revolves around identifying which product will not be obtained in a Wurtz reaction, exploring the mechanisms involved, and considering the role of resonance structures in the stability of intermediates. The scope includes theoretical aspects of organic chemistry and homework-related problem-solving.

Discussion Character

  • Homework-related
  • Exploratory
  • Technical explanation

Main Points Raised

  • Some participants assert that one product will definitely be the major product, while questioning the implications of C-14 shifting position inside the ring.
  • There are suggestions to draw resonance structures of the radical or ionic intermediates to aid understanding.
  • Participants discuss the energy requirements for certain conversions, with some questioning whether the necessary energy is presumed to be available.
  • References are made to the allyl radical, with one participant acknowledging a recurring difficulty in identifying it.
  • A link is provided to an external resource that offers an overview of the resonance stability of allyl ions, radicals, and anions from a molecular orbital perspective.
  • One participant mentions a previous encounter with the allyl concept in a different problem context.
  • Another participant suggests keeping allylic resonance in mind when encountering double bonds, though they express uncertainty about memorization techniques.
  • One participant concludes that the answer to the original question is product (d), implying some level of confidence in that identification.

Areas of Agreement / Disagreement

Participants express varying levels of understanding regarding the allyl radical and its implications in the Wurtz reaction. There is no consensus on the identification of the product that will not be obtained, as the discussion includes multiple viewpoints and uncertainties.

Contextual Notes

Some assumptions about energy availability for reactions are not fully explored, and the discussion does not resolve the complexities of the mechanisms involved in the Wurtz reaction.

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?
IMG_20181130_204553.jpg
 

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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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