Wurtz Reaction

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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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Answers and Replies

  • #2
TeethWhitener
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It might help to draw out the resonance structures of the radical/ionic intermediate.
 
  • #3
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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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  • #4
TeethWhitener
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Well, won't that conversion require additional energy?
Why? Maybe draw the hydrogens explicitly.
 
  • #6
TeethWhitener
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Won't THIS ↓↓\downarrow require additional energy?
Google "allyl radical."
 
  • #9
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I don't know why, but I still don't have a keen eye spotting the allyl radical. Get me?
 
  • #10
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You might remember I stumbled upon this 'allyl' thingy even in that "same SN1 & SN2 product" problem.
Anyway, Thanks again.:smile:
 
  • #11
TeethWhitener
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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
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I forgot to mention that the answer would be (d). You might've already guessed that.
 
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